Jen Abel's 15-Step Map of an Enterprise Deal, From First Message to Signature
Lenny's Podcast
On her third appearance on Lenny's Podcast, Jen Abel, co-founder of JJellyfish and GM of enterprise sales at State Affairs, walked through one enterprise deal from the first outreach to the signed contract, step by step. Her central claim is that most people treat enterprise sales as a five-stage process (intro, demo, proposal, contracting, closed won or lost), when a real deal involves closer to fifteen distinct steps, several of which most sellers skip. Abel's recurring theme is information edge. Each extra conversation is a chance to learn something competitors don't know, and a chance to make the buyer feel they are building the purchase themselves rather than being sold to.
Why a playbook is only 80% of the job
Lenny Rachitsky asked why Abel gives this material away. Her answer was that the playbook only goes so far. Sales is one-on-one, and the variable is another person. Some buyers want small talk, some want to get straight to business, some are technical and some are not. If you ran the same flow every time, Abel said, it would probably miss about one in four times. The steps cover roughly 80% of the work. The other 20% is how you make someone feel, whether they feel heard, whether the conversation was fun, and whether you told a good story. She added that she posts this material on X partly because it works like a diary that keeps the ideas fresh for her.
She also argued that the process is the same whether the deal is $100,000 or $1 million. Her explanation is that enterprise organizations are more sensitive to the process a seller takes them through than to the product demo itself.
The case study: AI legal tech sold to SpaceX
To keep things concrete, Abel chose a hypothetical: selling an AI legal product to SpaceX's legal team, at a deal size of about $100,000. She picked SpaceX because it has been in the news and everyone is probably targeting it, so it is a hard logo to win. It is a technical company, but the target is a non-technical team. She picked legal because, in her view, it is the largest line item in enterprise budgets, sometimes three to four times other budgets, and "there's always more money for legal." Rachitsky joked that this explains why there are so many legal AI startups.
Step 1: Landing the meeting with the "pincer" model
According to Abel, there are only two useful entry points. The first is the top executive, which in this case is the general counsel or chief legal officer (titles vary, but the weight is the same). The second is the "N minus one," the person one level below, usually a VP or director. She acknowledged that others would disagree, but she would not target anyone further down. Her reasoning: below that level, the storyline turns into a game of telephone. You end up learning about user value from someone far from budget and executive discussions, when a $100,000 deal needs an executive sponsor to allocate the money.
She calls the approach the pincer model. The founder goes after the executive and the account executive or enterprise sales lead goes after the N minus one, working from the top and the floor toward the middle. The goal is for at least one of them to respond. Because the two contacts are only one step apart, whoever responds usually pulls in the other. The founder can ask who else on the buyer's team should join, or the AE can offer to bring in the founder and suggest including the boss. She described this as a parity rule: each side matches the other's seniority. Abel was firm that the founder is the best person to reach a corporate executive one-on-one, even at a Series B or C company, and that any founder building something meaningful should be "ecstatic" to get in front of SpaceX's chief legal officer.
To find names, Abel suggested asking OpenAI's or Anthropic's models who the chief legal officer and their deputy are, then gut-checking and searching from there. For channels, she said cold calling works for non-technical roles but not for highly technical people. Email, LinkedIn, and X also work. Enrichment tools such as Lemlist can find email addresses. She sometimes sends a LinkedIn note and then follows up saying she sent one, since most people don't check LinkedIn daily. C-level executives, she said, might notice a brand but won't respond to a marketing campaign. They respond one-on-one.
The two-to-three-sentence message: sell the alpha
The first message should be two to three sentences at most. Abel described two levels. Level one is the specific problem you solve, which has to go beyond "we're an AI tool," since every company has an AI mandate. What matters most is the second level, the alpha: what the executive can uncover or unlock by bringing in a new tool. New tools are risky and "no one wants it," so an executive who sponsors one and pushes it down through their organization needs something bigger than saving time on some activity. She compared these executives to founders of their own business units, who want to grow their influence, budget, or headcount. Rachitsky summarized it as selling an unfair advantage, and Abel agreed.
She also warned that "10x better" still sounds like a commodity. What breaks through, in what she called a "flood the zone" moment of everyone pushing into the enterprise, is a message about rethinking the business model or how the team is structured in the age of AI, not simply reducing resources. Her litmus test: if the executive brought this product to a board meeting, what would they say it lets them do? How would they show needle-moving impact to the COO or CEO? Because everyone is emailing the same people, the message has to feel different, and it should be refined over time as response rates come in. She added that if you cannot get an executive excited by your value proposition, you probably shouldn't be pursuing a top-down enterprise strategy. In her view, this is why founder-led sales matters: founders are the ones who work out that storyline.
Step 2: The intro call, the most important call of all
Abel called the intro call the most important one. It sets how the buyer thinks about and respects you, and it is the call where they are most open. Once things start to feel like a sales process, she said, buyers clam up. Almost all the information edge a seller can gain comes from this first call.
Her rules: keep it super informal. No demo, no slides. Have a one-on-one conversation for 30 minutes. If a C-suite executive is joining, the founder should be there too. She typically opens by saying she doesn't know if they even need the full 30 minutes, which puts the buyer at ease that she isn't trying to take their time. She frames the call as swapping intros, then asks the buyer to go first. The more she hears before speaking, the more precisely she can frame her pitch. Rachitsky noted this also means the buyer isn't sitting through the same pitch they hear from everyone.
Buyers usually give a short overview at first. Abel then asks broad questions: Do you have an AI mandate? How are you thinking about how work gets done today? What needs to change going into 2027 compared with 2026, if anything? She said the answers usually reflect conversations that have happened above the person, since change tends to come from the top. She avoids anchoring the buyer toward her product, because the more they talk, the more strings she can pull. In a made-up example, the legal lead says they want to bring more work in-house and rely much less on outside law firms. Abel would follow up by asking whether that is measured, what success would look like, and why now rather than next year, especially given everything else going on (in her role-play, a large IPO). The "why now" question is usually where buyers open up about how they want to restructure their team, and at that point the seller can present the product as the vehicle to get them there.
She spends roughly the last ten minutes explaining what her company does, while continuing to ask questions. Two more instructions stood out. First, do not record the call. Buyers may assume they are being recorded anyway, but they will not be open or vulnerable with a recorder present. Second, keep digging with "off the record" questions about what really matters to them, what they want to own, and how things unfolded. She cautioned that you can't simply pepper someone with questions; some people are poker-faced, and reading how far to go is improvisation.
Abel does not use a scripted pitch. She said every storyline she tells comes out slightly different, because scripts feel artificial and buyers sense they're being put in a box. This is why she thinks enterprise sales is so hard to hire for. In her words, "the most successful salespeople are not trained salespeople," which is why founders are good at it. They may be bad at following process, but they excel at pulling out information and getting people excited by a vision. She was equally blunt about frameworks: "the fastest way to commoditize yourself is to go into some sales script." BANT (budget, authority, need, timing) should stay in the back of your mind, but you should never ask those questions directly.
Qualification, vulnerability, and cost-driven buyers
Asked how often an intro call goes nowhere, Abel said two to three out of every four calls turn up something real. About one in four ends with her saying the gap between the buyer's maturity and her product is too big, and offering to revisit in a year. She attributed this mainly to maturity rather than talking to the wrong person, since knowing who to talk to is the enterprise AE's job, and so is disqualifying quickly.
Rachitsky raised the worry that drawing buyers out might feel manipulative. Abel's response was that buyers have budgets precisely to buy solutions to their problems. She also values it when buyers ask probing questions back, because that signals a real relationship. She recalled a client asking the previous week what her team's biggest learning of the year had been. Every product has bugs and gaps, she said, and being honest about them makes the process feel less like sales.
On buyers who only want to cut costs, she described two motions. In one, the buyer wants the cheapest way to do something low on the priority list, where 60% of the way there is fine and "no one's getting fired over it." In the other, the problem is high-risk, such as missed information, delays, or unfamiliarity with a new regulation in legal, and the seller can charge a $250,000–$500,000 land. Marketing and sales are driven by numbers, she said, while legal needs to stamp out risk.
Step 3: The follow-up call that co-designs the demo
In the standard pipeline, the intro is followed directly by a demo. Abel called the demo the carrot, since everyone wants to see what you described, and said you should use it as leverage to get the right people in the room. The purchase should never feel like one person's pet project. A director or VP needs the executive's fingerprints on it, and executives want the actual users to feel bought in. There will be a champion who drives the deal, and she noted that most champions are one step below the executive, but the effort has to feel collective.
So before the demo, she schedules another call with the champion. She asks for 30 minutes and expects about 15. On the call, she says she wants to make sure the right people attend and that she demos the right things, then asks what will resonate with the team. She might lay out five things the product can show, note that two seemed to matter in the first conversation, and let the champion decide. Often the champion wants those two plus a third that ties to their mandate. She may even ask the champion to raise a specific question during the demo, and the champion may suggest a better question. According to Abel, none of the competitors are taking these extra steps. The call ends by getting the demo on everyone's calendar for an hour.
She also asks whether to hold a pre-demo with one more colleague before the group session. The decision depends on how far along the buyer is: less certain buyers usually want to bring someone else in first. Abel pushes for a pre-demo because it means more intel. On that call she spends five minutes recapping what she has learned and asks the new person to add to it. By this point, two or three people are excited before the group demo, and the buyer feels they are building their own business case.
She described two ways to fail. One is jumping straight into a demo with no groundwork. The other is agreeing when an enterprise reaches out during due diligence and asks you to present to four or five people. Don't do it, she said. You are either a checkbox, or you are demoing with no competitive intel, and "you just lost the deal at that point." She summed up what wins: the buyer feeling the product is so close to who they are that it seems built specifically for them. You are always up against something, whether a competitor, an incumbent (most often), or doing nothing at all.
Asked where the time actually goes, Abel said she spends a lot of it reading between the lines of what buyers said, then confirming her interpretations on these smaller calls. She compared it to prompting a model: keep going deeper and the answers become more refined. "The whole game is to slow down to go fast," she said. All of this should fit within a 90-day sales cycle, depending on the buyer's maturity. The alternative, she argued, is selling the enterprise a $15,000 solution with nowhere to expand. In her view, if you are not growing from $100,000 or $250,000 to $350,000 or $500,000 the following year, it is not an enterprise motion.
Steps 4 and 5: Framing and running the demo
Step four is preparing the frame. On the preceding calls, Abel asks who will attend, what each person cares about, and what to avoid. The champion is now invested, since this is their chance to be credited with finding the tool. She also asks what a good demo looks like in that organization, for example how to split time between discussion and product.
In the demo itself, some attendees will not have been on any earlier calls. Abel restarts from the top (who we are, why we're doing this) but frames it entirely in the organization's terms, so newcomers feel it was built for them. She invites those newcomers to say what they want from the session so they "feel the love." She wants the process itself to feel different, not only the product and the pitch.
Her main instruction for the product walkthrough: 80% of the value comes from 20% of the product, and the earlier calls reveal which 20%. Don't demo everything without a reason. Showing extra features can unravel a tight narrative, because attendees start noting what they would never use, and enterprises then question paying for a tool when they would only use half of it. If buyers ask whether it can do something else, that's different; a response like "funny you say that, we just released it" reinforces the sense of fit. She described enterprise sales as very tight project management combined with very tight narrative and framing, and "a lot of improv," but she said it is doable because "it's just psychology."
On people who derail meetings, Abel said this is rarely a problem with executives, since it is hard to reach those titles while being long-winded. When someone does wander, she suggests parking the topic for a dedicated call.
Signs a salesperson is struggling, and whether AI replaces this
Rachitsky asked how a founder or sales leader can tell that a salesperson is underperforming. Abel pointed to three things: the time from intro call to demo, how many conversations happened between those stages, and whether the salesperson can say exactly what they will demo, why, and how they will open. Because every demo she has run has been different, she rejects the idea of a single scaled playbook for deals of $100,000 and up. When you are going after the logos every startup wants, you have to take a different approach, not "cram the pitch down their throat."
She said she isn't worried about AI replacing the role, because so much of it is human, such as whether you click with the person. She admitted she has had intro calls where the buyer did not appreciate how she ran them, and that this is fine.
Step 6: The post-demo debrief
As soon as the demo ends, Abel texts the champion and asks to call within five minutes for a raw reaction before they have talked to anyone else. Where did we lose someone? Where did it land? Does anyone need more time? She said there is always someone in the organization who could kill the deal, and the debrief is how you find and protect against that person. The information also helps later. If the deal goes quiet for two or three weeks, she can ask whether it would help to spend 15 or 20 minutes with a specific person to hear their concerns.
She defined the champion as the person who really wants the deal to happen and has been there from day one. That can be the executive, but in that case the executive still has to bring along the people below them.
Steps 7 through 9: Designing, preparing, and running the pilot
Step seven is agreeing on how a pilot and decision will work. Abel's preference is a very short pilot: two to three days, for three or four users. The champion (or the person closest to the executive) should be included, but not the C-level executive, who is not the real user. She will give up the pilot fee in exchange for this, because a short pilot lets her control the sales cycle. From experience, she said, people often spend about half a day in the product and get what they need, so a 48- to 72-hour pilot can cut two weeks off the cycle. If the product needs setup, she asks whether a sandbox can show the value even without the customer's data.
The other option applies when the product needs real integration with the customer's data. In that case, she recommends a one- to two-month pilot that the customer pays for, with the fee credited back if they move forward. A willingness to pay is "a huge, huge signal." She noted that the fee usually ends up coded as services anyway, and the credit starts the relationship on a good footing. The trade-off, she said, is a sales cycle roughly a month longer, which is acceptable because the price is probably higher. She tied pricing to cycle length: if you can close $100,000 in 90 days, do that repeatedly; if a deal takes nine months, you should probably charge $250,000–$300,000.
To keep a short pilot working, she onboards each user separately beforehand and gives them three specific, clearly described tasks. Success criteria are co-authored with the buyer. Users should not simply log in and wander, since that shifts the work back to them, and she said the seller's job is to take 99% of the work off the buyer's plate. When a user doesn't like the product, she asks what wasn't clear and where they got lost. The tighter the structure, the more consistent people's experiences are.
Before anyone enters the pilot, Abel works backward from a successful outcome. When do we want signatures? Can we close by the end of next month? Should procurement be involved now or later? Is there a security lead for due diligence? Whose paper will the contract be on? If the answer is that a commitment is a quarter away, she recommends delaying the pilot rather than burning momentum. Once the stages are used up, you have nothing left to move the deal forward.
Pricing, worked out with the champion
Pricing comes up after the demo and before the pilot. Abel avoids discussing it earlier because people who missed the initial conversations may see a number three times their current spend without understanding why. By this point, she said, a buyer who was really worried about price would have raised it. If pressed, she gives a ranged ballpark, for example "somewhere between 150 and 250," with many dependencies.
The detailed pricing conversation happens one-on-one with the champion. She tells them the price, asks how they will make the case internally, what they would cut, and whether a slide showing ROI would help. She expects one of three responses: full alignment, no strong concern, or "I don't know if I can go to bat for this number." In the third case, she doesn't offer a discount or name a number. She asks the champion to help figure out what would work. This is the one point where she puts the burden on them, because they might ask for $20,000 off when she would have gone much lower, and "you don't want to negotiate with yourself." One option is a two-year deal that steps up to full price in year two.
Forward deployed engineers
Rachitsky asked about forward deployed engineers (FDEs). Abel said her views go back and forth. If an FDE is there to take work off the customer and speed up the deal, she is fully in favor. If the FDE is needed because the product is too complex for customers to use alone, that is a bad sign. She said the model makes sense for a company like Palantir, whose multi-million-dollar deals support it, but a full-time engineer on a $100,000 deal makes the economics messy. She thinks FDEs fit better for expansion than for landing. Rachitsky noted that some account managers now simply use the FDE title, and mentioned that Palantir people have called FDEs at most companies "sparkling sales engineers."
Why the five-stage CRM pipeline is not a sales process
With nine steps done, Rachitsky returned to the five-stage pipeline. Abel said those stages exist for weighted forecasting. For example, an intro might be weighted at 10% of deal value, a proposal at 50%, and contracting at 80%. They are buckets for the pipeline, not the steps you take a customer through. In reality, she said, there are three to five critical meetings inside each bucket. Asked what share of founders and salespeople get this wrong, she said 90%. Her explanation is that enterprise sales should mirror, and try to control, the customer's buying process, rather than forcing customers into the vendor's process. For a $1 million deal, she would add more upfront meetings. For a $100,000 deal, a seller can move somewhat faster as long as qualification holds.
Step 10: The post-pilot session
After the pilot, feedback can come through a survey, one-on-one conversations with users, or the champion checking in internally. Abel stressed understanding what users actually did: time spent, bugs, which features they used. If most users only tried two of the three tasks, you want to know why before the review, so that a complaint like "we wish it did this" can be answered with the fact that it does and nobody tried it. During the pilot, she may tell the champion that someone logged in for 15 minutes and never got past step one, and ask them to check in, without telling users how to do their jobs.
She described the enterprise as built to have as much friction as possible: people who can kill the deal, procurement, legal, and finding the executive sponsor. The insider champion is the key to getting through it. When the champion goes quiet, that's the warning sign. A champion who has spent enough time with you will often call and say, "if I'm reading the tea leaves, we should sit on this for a minute." Rachitsky noted that silence is an easier way for a buyer to say no than confrontation.
Win rates and funnel benchmarks
Abel defines a qualified opportunity as one where you are talking to the right person, they are excited by the alpha, and they admit change needs to happen. She deliberately said "change" rather than "problem," because everyone pitches the same problems and that commoditizes you.
Her number for a healthy enterprise win rate, from qualified opportunity to signed contract, was about 30–35%, which she later adjusted to 25–35%. Her reasoning: if your win rate is higher than that, your price is too low. Some of the market isn't mature enough to buy, and those gaps are normal. Keeping prices consistent also matters because "the market talks." Charging one buyer's friend $50,000 and another company $500,000 will come out, especially among executives. Rachitsky said he sees exactly this kind of price comparison in founder WhatsApp groups. Abel added that roughly another 25% of lost deals come back a year later.
She gave rougher numbers for the funnel stages, and they shifted as she spoke. If targeting is good, about 50–75% of contacts become qualified leads. About half of those reach a demo, and a quarter advance beyond that. After that, she said, you shouldn't lose many if qualification is solid. From the pilot stage, she expects about 80% to succeed. If fewer do, either qualification is off or the seller has oversold a product that isn't ready. Smart buyers always want a pilot, she said, so it should be a standard part of the process.
Steps 11 through 14: Procurement, redlines, and signature
Step 11, papering prep and procurement timeline. Abel writes up the pre-pilot agreement in an email the champion can forward to procurement: what was agreed, pricing tied to signing by a certain date, and an incentive for hitting that date. "There's always got to be a reason to create urgency." She sends the contract as a Word document, not a PDF, because the buyer will redline it (and most enterprises can't access Google Docs). She asks whether they want to use her paper or their own, since using theirs is sometimes faster. She also warned that buyers often blame procurement to avoid giving bad news, saying the deal is "lost in procurement." In her experience, procurement is usually a roughly 30-day process, and its job is not to kill deals but to make sure the purchase matches how the company buys. Procurement is also the only path to getting paid, since business unit leaders can't pay you directly; payment comes from finance. Her advice is to start no implementation or onboarding until the contract is signed.
Step 12, paper review. Redlines will come back. Accept the easy ones. If there are many, ask to get the buyer's legal team on a live call instead of trading documents back and forth. Push on the terms that affect the business, let the rest go, and have your own lawyer review. ("Paper," she explained, is corporate-speak for the contract.)
Step 13, the procurement process. On the live call with procurement and legal, you work through the terms you can't accept. If the buyer's paper is used, it will contain "the kitchen sink." For example, if they ask a small company for $10 million in liability insurance, you can argue their exposure isn't that high. Everything is negotiable, but pick your battles. At this stage, she said, a deal won't fall apart over a clause; the work is making sure they understand your position.
Step 14, signature. Find out ahead of time who the signatory is, which is sometimes the CFO rather than the executive sponsor, so the champion can nudge them if signing is delayed. Asked how salespeople celebrate, Abel said the good feeling lasts about five minutes before they ask "what's the next one?" In sales, she said, you are only as good as your pipeline.
After the signature: expansion and services
For expansion, Abel said that a mature company will already know which products a customer can grow into. For companies closing their first ten enterprise customers, she thinks the founder should be involved after the deal to see which parts of the product are custom to that customer and whether to charge for services. Even though most companies focus on recurring revenue, she noted that services remain the largest line item in budgets. Enterprises know how to buy consultants and lawyers, so there is always money for services.
How buyers can say no without wasting time
Rachitsky asked the reverse question: how should a buyer end a process that isn't a fit? Abel's advice was to explain as early as possible why the timing isn't right or why the organization isn't mature enough. She said the team has to be structured to take on the technology. As mentioned earlier in the conversation, she noted that sometimes it's easier to sell services first and guide the customer toward the technology later, though sellers further along in enterprise maturity should lead with technology.
Buyers should also expect pushback. Abel has told hesitant clients that "you are a liability not closing this gap," while acknowledging you have to be in a position to say that. She reminds them of what they said on the first two calls, and if they are just "in a weird spot," she suggests starting smaller. But when there is a real barrier, such as an acquisition that freezes new vendors, she said you have to respect it.
Sales as product management, and where AI fits
Rachitsky observed that the whole process looks like product management: staying on top of many small tasks and trying to understand people's pain points so you can solve them. Abel agreed that the two roles are surprisingly similar. He also pointed out that AI barely came up in the conversation. Abel said that AI-generated reports or imagery sent to clients feel salesy because anyone can make them, and Rachitsky tied that back to the episode's question: what is your alpha? She also repeated her earlier advice to write your own emails rather than using boilerplate or AI, saying emails are "living and breathing" and recipients can practically hear you reading them aloud. She ended by inviting questions and noting that State Affairs is hiring for multiple enterprise sales roles, promising to teach new hires everything she knows.
So, we're going to do something really unique with this conversation. Basically, go through the enterprise sales life cycle step by step. Let's set this up.
Let's start with how do I even get the first meeting? We're in this flood the zone moment of everyone trying to break into the enterprise, but like what exactly are you solving for them as a problem? That's level one, but most importantly, the alpha and it needs to be different.
Step two is basically running the intro call.
This is the most important call out of all of them. This is what I like to do. Super informal. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call.
What are the benchmarks for how often you get through each of these stages?
The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low.
What are some signs that your salesperson is not doing a great job?
The most successful salespeople are not trained salespeople. Fastest way to commoditize yourself is to go into some sales script. Budget, authority, need, timing. Like that should be in the back of your brain. You never actually ask those questions.
What percentage do you think are just doing it wrong?
90%.
Wow.
Like it's literally so fun. People read these sales books, go to these sales trainings, they try and take someone else's game and run with it. And it never works that way. Most people think the sales process is five steps and we're already in step 10 and we're not even done.
The worst thing you can do in the sales process is
Today my guest is Jen Abel. This is her third time on the podcast. For those that don't know Jen, she's co-founder of JJellyfish, GM of enterprise sales at State Affairs, and most importantly is the person that I've learned the most from about the art and science of enterprise sales. In our first conversation, we went deep on founder sales. In our second conversation, we focused on the $1 million to $10 million enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a five-step process. It turns out it's closer to 15 steps.
Most people ignore a bunch of these steps that you'll hear about. We go through everything that you need to know at each step to significantly increase the odds that you close your deals. This episode is incredibly tactical and specific. You will learn a ton. I did for sure. Like I say in the episode, I always get so energized and just excited to sell something after talking to Jen. You will feel the same way after this conversation. I'm so thankful to Jen for sharing so much alpha with us. Before we get into it, don't forget to check out lennysproductpass.com for a free year of the hottest and most beautifully crafted AI products in the world available exclusively to Lenny's Newsletter subscribers. With that, I bring you Jen Abel.
Jen, thank you so much for being here. Welcome back to the podcast. A very rare third visit to the podcast. How does it feel?
Round three. Super excited to be here, Lenny.
I'm even more excited. So, we're going to do something really unique with this conversation. I've never done anything like this before. We're going to basically go through the enterprise sales life cycle step by step. You'll talk about this, but many people think it's like five steps. You talk about how it's actually something like 15 steps. A lot of people ignore a lot of these steps. And the idea is I want to create a very concrete and tactical playbook for how to do enterprise sales.
Okay.
We've had conversations, secrets.
All, let's go. Just suck them all out. Make everybody amazing at sales. It'll be great.
Awesome. And you know, this touches on just like why I think the podcast is really helpful to people and just the Valley vibe even though you don't live in the Valley. Just like there's so much win-win-win in helping people learn these things, you know, it may feel like why is she giving away all these things? But maybe actually let me ask you that, just like why do you share these things?
Well, it's so interesting because there's so much art to this that even if you gave someone a 15-step playbook, there's so much of a feeling that you have to go off of. Like sales is one-on-one, right? You're dealing with a variable, which is another individual. And if you ran the same flow every single time, it's going to probably not hit one out of every four times because everyone's different. Like some people like to joke, some people like the small talk opener, others want to jump right into it, some are technical, some are not technical, you know. So everybody's so different that even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of like how you make someone feel, do they feel heard, did you make it fun, did you tell a good story? I mean, that's also a huge part of this. Too much to cover today. So, we'll stick to the road map of like how to close these deals. But
I think the interesting thing about enterprise sales is even if you sell a $100,000 solution, it is the same exact process to sell a million-dollar solution. So that's why it's an interesting process, because the enterprise organizations are more sensitive to the process you take them through from a sales motion than they almost are with demoing the product.
Amazing. And I'll just give a plug for if people want to continue learning, your Twitter feed is just the best. You share all this stuff constantly.
Yeah. And I think you talk about there's like rational reasons to share this stuff, but it feels like there's just like I just need to get this stuff out. People need to
It's like a diary and it also helps me like keep it in my mind too.
Right?
It's like my own education.
Yeah, I know exactly what you mean. That's why I started writing. I was just like I just want to remember this stuff myself. I'm just going to share it and crystallize it.
Okay. So before we get into the steps, let's set this up. What are some things people should know? What's kind of like the case study of what we're going to be using here?
Let's use a company like SpaceX, right? Recently, you know, has seen massive news pressings. You know, everyone's probably targeting them, right? So, it's going to be a hard logo to go in and win. They are a technical organization, but I think what we do is target a non-technical team. So, we're going to like really get into like the nuance of this. So, let's do SpaceX. Why don't we pick legal? Let's have some fun with legal. The interesting thing about legal, it's the largest budget line item in the enterprise kind of budget, right? Sometimes three to four times other budgets and it's forever. There's always more money for legal.
That's why there's so many legal AI startups. I get it now.
100%.
Amazing. And I'll just add the reason I love to have you on this podcast is I've left both of our previous conversations just like fired up about selling. I have nothing to sell, but I'm always feeling like I want to sell something now. I feel like I've learned all these things. It feels so fun.
Sales. You're a master. You're actually a master at this. Sales is marketing. Marketing is sales to some extent, right? And
All right. You do that better than a lot of people. I feel like you're using some sales technique on me to make me feel good about myself. Okay. Anything else before we get into step one of the enterprise sales cycle?
No, I think it's just good. SpaceX and targeting the legal function.
And then like a 100K, let's say, deal. And to your point, it's the same process whether it's 100K or a million. And I will add a plug for a previous episode. You talk about why you want to be at least 100K something as a deal to be a real enterprise company that will survive because the ROI and just the whole economics of that stuff, but we won't get into that.
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Okay, step one, where does it start? How do you start selling someone on your product?
It's a great question. So, I think we'll start with like how do I even get the first meeting? How do I even engage with these people? There's so much nuance as you target, as you know, as we're using the case study of SpaceX today. You have the top of the rung, right, which is the general counsel, the head of legal, the chief legal officer. They all kind of have slightly different titles, but they all carry the same weight, which is like who's the lead of the team? And then underneath that, you have a bunch of people that carry a VP title, carry a director title, maybe just say lawyer on their LinkedIn.
So you have to do the work to figure out what is my entry point. And there's only two entry points. Starting at the very, very tippy top, meaning going direct to the decision maker, the chief legal officer, or finding the individual that would be maybe one step removed. Okay, I personally, other people would argue with this, I personally would not be targeting anybody else. It is the executive themselves or an N minus one.
Okay, so let's talk about like why. In order for an enterprise deal to move forward, you need to have this extremely compressed storyline that lands immediately to the objective that they want to solve for at the organization. It has to go beyond just an AI mandate. I think every company today has an AI mandate and I know everyone is an AI tool, but like what exactly are you solving for them as a problem? That's level one. But most importantly, the alpha: what does this executive uncover and unlock by bringing in a net new tool? Because bringing in a net new tool, okay, is risky. No one wants it.
So if we're targeting the chief legal officer and the N minus one, you get two to three sentences max. Okay, that might be through an email, LinkedIn, that might be through a phone call, that might be through an event, or that might be through some marketing capability. Most C-level executives don't respond to marketing. They might see your brand, they're not going to respond to a marketing campaign, okay? They will respond one-on-one. And the best individual to one-on-one to a corporate executive is the founder. Even if you're a Series B, Series C, right? The founder should be ecstatic to want to get in front of the chief legal officer at SpaceX. I think any founder that is, you know, building something really meaningful knows the important role of that.
Second is you can get your AE or enterprise sales lead to target the N minus one and you do what I call the pincer model, because you're going after two different people and trying to get them together. It's actually called the pincer model, which is start at the very, very top, find that kind of floor, and work in between them.
Okay. So these are the two layers you want to be targeting in landing that meeting, because if you go any further than that, you risk they're not going to be able to communicate your storyline. It's a game of telephone, right? And now you're learning from someone that is not near the budget or the executive discussions, right? Which is super risky because now you're learning about user value, not executive value. And a $100,000 deal needs an executive sponsor to sign off on it to allocate the budget. And this is why you need to start at these two layers only.
Wow. There's going to be fractals of questions and things to dig into with each of these steps. This is amazing. I love how just how specific and tactical you are with all of these things. I'm going to try to summarize a couple of these tips and then I have a follow-up question. Okay. So tip one is go after either the exec, so in this case, it'd be general counsel, head of legal sort of person, or N minus one. Love that way of describing it. Maybe a VP. You want to pitch them two or three sentences in like a text or email or at a conference. And the key is to focus on the alpha, like what your product will unlock for them. Love that. And it sounds like there's still like here's the problem we solve for you, but here's really the alpha we unlock.
Correct. Because for an executive to bring something in and be the sponsor and like share this and disseminate this down their command, they need to stand behind something beyond, hey, we're going to alleviate, you know, the time it takes to do X activity. That's not big enough. They're like a founder too of their own business unit. Like you got to sell the vision and how are these people going to get to the next stage, whether with their influence, get more budget, get more people, however they want to define that.
Yeah. So it sounds like they want to win, and to win you need something, an unfair advantage. That's exactly what you're pitching.
That's exactly right. Yep.
Okay. And then this pincer move. So the idea here is for the exec, say chief legal officer, general counsel, the founder needs to reach out.
Yep.
And then the AE reaches out to the N minus one contact and you go from both directions.
Yep.
And I imagine the goal is at least one of them responds.
That's correct. And then because you're only one step removed, they'll usually loop in that next person, or the founder could say, "Hey, I'm going to loop in my so-and-so colleague. Who on your team should we also include?" Or an enterprise executive could say, "Hey, I'm going to bring in my founder. Could we see if your boss might want to be a part of this, too?" It's that parity kind of rule.
Yeah. And they might be like, "Wait, I've heard of that. I think I heard that name before because I got this other email."
Exactly.
They may not remember. Okay. Two questions. How do you find this N minus one person? Any tricks? Is it just sitting on LinkedIn kind of figuring it out? And then two is any channel recommendations these days? Like what's the best way to try to contact these people?
So you can spar with OpenAI and Anthropic to let them do the quick scan of like, hey, I'm looking to target the chief legal officer of SpaceX and their deputy, who are possibly people I should be targeting, and then go off that and do your own gut check and search from there. But usually they'll give you the proper names. Now here's the interesting thing about this. Everyone
is probably also targeting those people. Okay? And this is why you need to be, and we talked about this in other episodes, it needs to feel so different and it needs to be about alpha. And if you don't have executive value, meaning you cannot get an executive excited by your value proposition, then you probably shouldn't be moving up into the enterprise doing a top-down strategy.
Got it. Okay. And then in terms of trying to reach out to them, any tips? Is it like the tools there to do to figure out their number, whatever?
They're all so unique. Cold calling works. Again, it depends on the role. You're not going to cold call a highly technical person, but a non-technical person, it works. Email, LinkedIn, Twitter.
Are there tools to find these emails and things? Is there something you recommend?
Yeah, there's a ton of tools that do enrichment. I'll try LinkedIn first and say, "Hey, I shot you a note on LinkedIn. I just want to make sure you got it." Most people don't check that on a daily basis, but yeah. I mean, you have Lemlist and all sorts of these enrichment tools that can give you the email, but I think the number one thing is assume they are getting hit with hundreds of emails. How are you going to message your storyline to stand out? And that's not easy to do, and that's really why I think, going back to our first episode, founder-led sales is so important to figure that piece out.
So that was my next question: what are some examples of two to three sentences, if you have some in your head, maybe even from your current job, that you think are good examples of this two-to-three-sentence pitch?
Yeah, I think it comes down to what is the differentiator to what you were offering, not even what do you do 10x better, because to them it still sounds like a commodity. How are you rethinking the business model? How can you help them rethink the way that they're structuring their team? We're in this flood-the-zone moment of everyone trying to break into the enterprise, and the number one thing that breaks into the enterprise is, "Oh, the way I'm modeling my business unit, here's how I should be thinking about it in the age of AI." And it needs to be different. It can't just be, "Oh, we'll help you reduce the number of resources here." No, no, no. How are they going to show needle-moving impact to their COO, CEO? If they were to bring it to the board meeting, what would they say about the product? "This product will allow me to do what?" That's the litmus test.
Is this a pitch that you iterate on over time? Because you're probably getting some percentage of people responding. So okay, so the advice is keep trying to reframe this.
That's exactly right.
Awesome. Okay, anything else on the first reach out before we get to the next step?
No, I think that's good.
Okay, let's do it. I started shaking your head before you said it, in case people are confused. Okay, step two. Step two is basically running the intro call.
Yes. Okay, this is the most important call out of all of them. Okay, because you are setting the tone with how they think about you, how they respect you in your role, in your craft, and the information they will tell you on the first call, they will clam up moving forward because it starts to feel like a sales process. So all of the information edge you can gain as a seller is on this first call. Okay? So keep it, and this is what I like, super informal. Don't show them anything. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes.
Okay? Now, again, if they're bringing in a C-suite executive, you better have your founder join that call as well. I don't know any founder that wouldn't want to be in the room with a Fortune 100 C-suite executive. So make sure you bring in your founder if you have that person on, but let's say you had the N-minus-one, you had the VP out. Okay, super brief. This is how I typically open: "Hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes." Put them on the back for, like, "Oh, this person's not trying to take up my time." "All I would like to do is swap intros, and if it makes sense, we can always get on another call and go much, much deeper. But I just want to better understand who you are, and I'd love to share what we are doing and why I specifically reached out to you." So I say, "Would you like to go first?" Always let them go first. Give yourself the edge, right? Because the more information you are receiving before you speak, the more you can frame it and tighten it to what they specifically care about. So
And they also aren't sitting there now listening to a pitch like everybody.
Yeah. Exactly. Now they're talking. Now they're conversing. Now it's like, okay, now it's fun. Now this person's not pitching me. I'm in a conversation and a dialogue. Okay. So now you're talking to them, and they usually do a very brief overview, and they're like, "Hey," we didn't get a chance to look up the chief legal officer at SpaceX. Obviously, this is just a case, but whoever that person's name is, "You know, I oversee the legal team and blah blah blah." Okay, great. They usually don't give you much. So they say, "Okay, interesting. How are you thinking about, do you guys have an AI mandate going on at the organization? How are you thinking about the existing way you guys are doing work? What are you looking for going into 2027? Does anything need to change?" Ask, does anything need to change? Because again, what they're going to usually default to is what conversations have happened above them and have been transcended down. So the change is usually dictated from the top, which is great. So, "What needs to change going into 2027 that you did in 2026, or maybe not at all?" And that's when they start to open up.
And again, you don't want to be too pointed of anchoring them towards your product, because again, the more they speak, you can start to pull on the strings that matter. So they could say something along the lines of, you know, I'm making this up at this point, "We are really looking to figure out how to bring more of this work in-house and rely far less on external law firms, right? Because now we have more tools and capabilities." Okay. "Is there a measurement to that right now? What does that look like internally in terms of if you've done that successfully in 2027?" And then they'll say, you're trying to understand how mature is this thought, right? Okay. So now they're going in and they say they can't really answer that fully, because, okay, "Why is that important now? Why not wait another year? I mean, you guys have so much going on. You just had this massive IPO. What's causing the team to want to reshape this or rework the way that they're managing internally?" And that's usually the moment where they start to really guide you in terms of how they want to structure their team. So now you're getting all of this information about where they want to go, right? Now when you talk about what you do, now you're the vehicle to get them there, right?
And so I try and spend maybe 10 minutes, the back 10 minutes, explaining what we do and just keep asking them questions. Be like, "Oh, that's so interesting. What an exciting role to be in." Be like, "Okay, full disclosure, right?" And by the way, I take a step back to that. Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable. They might assume it's being recorded, because I think everyone kind of operates under that assumption right now. But for the benefit of yourself, do not have a recorder present. Okay? "Off the record, between the two of us talking right now, of what you just shared, what really matters? What do you want to own? Or what's the chronological..." Keep digging, digging, digging, because the more you dig, the deeper you go, the more information they give. Okay, now you can't sit there and just pepper them with questions. This is that art piece of how open is this person. Some people are poker faces, some people are not. You will be able to go much deeper with some and not deeper with others. You just have to improv.
Okay. But after you now have that intel and you can now understand, okay, here's the frame I'm going to take, now you can give them the pitch. Okay. I will confirm every single conversation I have, the storyline that I tell looks slightly different. I do not have a scripted pitch or frame for any call, because it feels artificial. They feel it. It feels like you're putting them into a square box. The best thing you can do is listen actively and then feel confident enough to craft the pitch around what they just shared with you.
That last part seems really hard, to adjust and make up, like, here's what you're focusing on and here's how the product is going to solve that problem for you. So that's kind of where that art and skill comes in.
That's right. In enterprise sales, it's so, so hard to hire for, because the more someone is trained in sales, the less natural it feels. I know this is counterintuitive, and we spoke about this on another call. The most successful salespeople are not trained salespeople. That's why founders are so good at this. They don't give themselves enough credit. What are they not good at? Probably following this process. What are they great at? Pulling out information, pulling on strings, getting people excited by vision. No one can do that better than they can.
What percentage of the time are you just like, "Okay, this isn't actually going to help you that much"? So, just, we'll share we're up to... Okay, you're nodding, that happens.
I would say two to three out of every four calls there's something real.
There's something real.
Yeah, there's something real. One out of every four calls I'm like, "Listen, based off of the maturity of where you guys are and where we are, it's too much of a gap. I'd love to revisit this in a year, once you guys have a chance to solve for X, Y, or Z." That's such a great question about the qualification. Most people are not going to be qualified, not necessarily because you're talking to the wrong person, because if you're an enterprise executive or enterprise account executive, your job is to know who to talk to. Okay. And your job is also to quickly disqualify someone. And it's probably one in every four calls.
Awesome.
Simply because of maturity.
Cool. So you don't have to have this intense pressure to nail it on every call and here's the pitch. Okay. Awesome. What I also want to comment on is this idea of getting them to share a bunch. It may feel tricky, like you're tricking them into sharing all this, but really they have problems they want to solve, and you're there to help them solve a problem. And so why would they not want to just, like, "Okay, here's what we need help with. Here's the problem. Here's our priority." Their job is to buy solutions to these problems, right? That's why they have budgets.
Right. So that's why the fastest way to commoditize yourself is to go into some sales script like budget, authority, need, timing. That should be in the back of your brain. You never actually ask those questions.
Cool. Okay. So the core lesson here is focus on learning and extracting their priorities. And what I felt as you push them to get more real and really pressure test how big of a deal are these, why is this important?
Because you want them to ask you those questions, because that's when you know you're building a relationship. I had a client last week say to me, "What's the biggest learning your team has had this year?" Every product needs to get better. Every product has a bug. Every product, you know, isn't able to do X or Y as well as they said. And I'm like, "That's a really good... that's so funny. We just had a conversation about that," and she was like, "Thank you for sharing." They just want to know you're vulnerable, because then it feels less like sales.
I imagine priorities for a lot of companies these days is saving token costs. I know classically you don't want to focus on lowering costs as a sales pitch, "This is the cheaper option." Yeah. Thoughts on if that just comes up a bunch? Like legal, "We just need to save costs."
Yeah. So in pricing, there's usually going to be two motions. "I need the lowest cost way to do X because it's low on the totem pole, and I really don't care if it's 60% of the way there. No one's getting fired over it. I'd rather just save budget." Or you're solving a problem that you can charge, you know, a 250–500K land, because it is high risk. If you're dealing with legal, there's high risk to it, right? Missing information, being delayed on something, not having people understand the importance of some new regulation or law, not being buttoned up. So I think every organization looks different, right? Marketing and sales, it's very clear that numbers drive them. For legal, they need to stomp out risk.
Awesome. So yeah, basically this comes back to the idea of alpha and upside. The more you can be in that bucket, the more you can charge, the easier everything gets. Okay. Anything else before we get to step three?
No, I think for step one, that is the most important meeting, and I feel like people just spend so much time talking about themselves and miss all the competitive advantage to win the deal.
Yeah, your point about how as a buyer it's so low pressure at that point. You're just exploring, and so I could see why people come into it like, "Cool, let's learn. Let's see if this..." versus you're in the funnel, like, "Oh, I gotta actually make a decision. I'm gonna have to let them down if I don't want this." Yeah, that's like dating.
Yeah, their openness to share more starts to clam up a little bit more. But we'll talk about how to make sure that doesn't happen, too.
Amazing. Okay, great. Great foreshadowing. Okay, so step three is running a follow-up intro call.
Yes. Okay. So usually right now the stages that most people have is intro, demo, proposal, contracting, you know, closed won or closed lost. There's five stages. They're very basic. People usually go from an intro call straight to a demo. Okay. The demo is your carrot in the process. Everyone wants to see this amazing thing you just spoke about. Okay. So your job is to make sure that when you do that demo, the formal demo, you have the right people on the call, because if you don't, one, you lost your leverage to organize that group and rally them. But more importantly, you never want it to feel like one person's baby, right? If you're selling to that director or that VP, you need to make sure that that executive feels like it's part of their baby and they're helping craft it and they have their fingerprints on it. And vice versa, the C-suite wants the actual users to feel like they were bought in on this, too. Okay?
So you want to make this, and this is the tricky part, there's going to be someone that's going to champion it and get the deal done, but you've got to make it feel like a group effort. Okay? So the person that you had the intro call with, that's who you built the rapport with. That's your champion at this point, whether it's the C-suite executive or one step removed. I say champion, most champions are one step removed. But let's just say the C-suite executive has delegated this now to the champion
...to navigate. Okay, for that demo call. Now, before you do the demo, get on another call with them. "Hey, I had so much fun on our first call. I think that there is a great opportunity to support you guys." This call should be 15 minutes, by the way. "I'd love to do a demo, but before we do the demo, I want to make sure we have the right people in the room and I'm demoing the right things. Can you help me understand, from the conversation we had earlier and as I'm walking you through the product, what do you think would resonate with the team?" Now you're collecting more intel.
Okay. Now it starts to feel like, oh great, now they get to put their fingerprints on this. So it's like, "Okay, when we demo to this group, at this point I want this question to be asked. Can you ask this question in the meeting? Because I want them to understand the value." And they'll be like, "I'm actually going to ask this question because it's going to resonate more." So now you're building this demo alongside this internal executive, and none of your competitors are doing this.
No other startup you're competing with is taking these extra steps. You now have the alpha of the intel they are giving you from these conversations, and now they feel part of this journey. Okay, now they trust you.
So it's like, okay, now you're spending 15 minutes, or 30, right? Sometimes they won't give you that much more time, but ask for 30, probably do 15, and say, "Here are the five different things we can go into. From our first conversation, it sounds like these two things matter, but let me show you all five." And then they might say, "Okay, I want you to do those two that we spoke about, but I also want you to show this, because this is also part of our mandate, and this will make it feel holistic."
Okay, so now you just mapped out the storyline with an internal partner on their end, and now you have the names of the right people. Now you're going to close that call. "Great. Is there a time we can look at everyone's calendar and put this on the calendar?" Make the meeting an hour. The demo should be an hour.
Okay. Now, you can ask before this meeting, "Do we want to do a pre-demo to maybe someone else on your team that would be excited by this before we race to the group demo? Or should we just do the group demo?" They know their organization better than anyone else, and how pressing this need is. Now, if they're less mature in knowing if they want something like this, they probably want to bring in someone else before the big group. If they're like, "No, no, no, this is something we want to really move into," they probably are ready to go into a group. So, you just need to figure out where they are on that maturity arc of their decision.
Okay. So, now you have: do we want to go into pre-demo? Do we want to assume they checked off pre-demo, or do we want to do group demo?
How often does that pre-demo happen?
I try and push for it because, again, it's just more intel.
Yeah. So, let's assume there's a pre-demo.
Okay. So now you have a new colleague on the phone, and you could say, "Hey, for five minutes I'm just going to catch you up on the things that I just learned from so-and-so. What can you add to that? What do you think?" Do you see how you're just collecting more and more intel along the way? So now you're building the business case for them. Now they feel like they're buying, not being sold to. Okay? So now you have two or three people at this point already excited for the big group demo.
The worst thing you can do in the sales process when you move into demo is just go into one straight demo with no problem. Or worse, an enterprise organization might reach out to you because they're going through a due diligence process to say, "Hey, we'd love to see what you guys have built. Will you present this to four or five people?" Don't do it. You're either a checkbox, and you want to remove yourself from being a checkbox. Or two, you're about to demo your product with no competitive intel. You just lost the deal at that point.
Enterprise deals are won on "This feels so close to who we are. It feels like it was built specifically for me." That's the whole game.
Amazing. I love just how much alpha not only you're sharing with us. It feels like the theme of this is alpha, just like the alpha we're getting from this conversation. It also feels like a lot of this process is you getting alpha from the team. I don't know if alpha is the right word, but...
No, it is. It's information edge. Yeah. It's the information edge that whoever I'm up against is not getting.
And you have to assume in the enterprise, you're always up against something. You're up against not doing anything at all, or you're up against a competitor who does some, or an incumbent, right? Most likely the incumbent. But it's so crazy to me how many people just spew out a pitch with no... You also have to make it informal and fun. People also buy from people they like, right?
I love how, so far at least, it feels very doable. Not that difficult. Feels like I could do this. And it doesn't feel like it takes that much time to do any of these steps so far. It's like a call, learn some stuff, think about it. Are there any time buckets that aren't obvious, where you spend a bunch of time on your own thinking about something?
Yeah. I spend so much time thinking about reading in between the lines of what they were saying, and that's when I will follow up, like those kind of pre-run calls before a big demo. I'm clarifying all those questions, like, "Hey, I know you said this. Did I interpret that correctly? Is that the priority?" And then again, they'll go deeper. The more you infer, the questions you ask... It's almost like you just have to keep prompting. It's like prompting humans at this point, right? Go deeper and deeper and deeper, and the answers you're going to get are just going to get so much more refined. The whole game is to slow down to go fast. All of this should be within a 90-day sales cycle, based off of their maturity.
To some people listening, this may sound like a lot of work. I imagine that this is what separates companies and products that win deals versus not. You know, you could have a better product, you could have a better price, a lot of things, but just not executing in this way through the sales process is probably shooting yourself in the foot.
Or you're stuck at... you just sold the enterprise on a $15,000 solution, which goes where? How do you expand that? The whole game is expansion. If you're not going from 100K or 250K to 350 or 500 the following year, it's not an enterprise motion.
Okay. So, just to quickly summarize, we're at step one, landing the meeting.
Yep.
Then running the intro call. Then there's this follow-up intro call, which you pointed out is often ignored and a big opportunity to improve the demo. I love the way you describe the demo. It's kind of this carrot that you're holding that you can use a little bit to extract more.
Yeah. And then step four is prepping the pitch and framing the demo.
Yeah.
Is there more to share there?
No, I think we're at the point where it's like, okay, now you're running a big demo, right?
Cool. Yes.
So now you have all of the people involved in the demo. You might have somebody that's involved from their AI team that's going to support some rollout. You want all of the people involved in this decision at that table for the demo. That's how important it is to not rush it.
Okay, so now you're running the demo. Before that demo, on one of those calls: who are all these people? What do they care about? And what should I avoid? The person that you've now built this relationship with can give you all of the intel.
At this point, they want this to go forward. Now this is like a great star for them, of like, "I found this amazing tool. It's going to solve our problems, and now I get to put my name on it alongside one or two other people," right? So for that demo, just make sure you know exactly who's involved, what these people care about, and what a successful demo looks like for them. I just ask them, "Hey, people do demos all the time. What looks good? 30 minutes of discussion, maybe 10 minutes of showing? 10 minutes of discussion, 40 minutes in the product? You tell me what the organization likes."
And on that demo, there's going to be people that were not a part of any of these calls. Okay? Your job is to take a step back and restart with: here's who we are, here's why we are doing what we are doing. And it's fully in their frame. You now have all the context to put this in their frame. So now these net new people are like, "Holy—this was built for us." Sorry for my French. Now they're leaning in, being like, "Okay, all right. This is very aligned with what we need."
Because they have no idea. You've talked to all these people. No idea. Learned what their challenges are.
They're leaning in, being like, "This feels different." Now, this is also the whole part of being different. Not only is your product different, not only is your pitch different, the way you're going through the sales process is different. She was like, "Wow, these guys are good." Okay. All right. So now you could let them talk. Let these net new people talk. Be like, "Hey, I know we haven't had a chance to speak. What do you want to get out of the demo today? I want to make sure I focus for you." Now you're leaning a little bit more into these net new people so they feel the love. Okay?
And then when you demo the product, 80% of the value comes from 20% of the product, and you have learned on these previous calls what that 20% is. Do not demo everything unless there is some reason to, because now all of a sudden this tight frame, this tight narrative you've just crafted and spent all this time with, just gets thrown out the door, because it's like, "Oh well, I wouldn't use that. I wouldn't use that. Well, everything she just shared, that's really only over here." And you could just blow the whole thing up. And the amount of times enterprises are like, "Hey, I don't know if we want to spend this much money for half the tool. We wouldn't use half the tool." Now all of a sudden, you've just unraveled all the work you've just done.
Enterprise sales is super, super, super tight project management and super, super tight narrative and framing. Owning that frame, owning that frame to exactly who these people are. And that's why this role is so hard. Okay? Because it's a lot of improv, and it's a lot of leaning in, and it's a lot of reading in between the lines, but it's stuff that is doable. I mean, it's just psychology.
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How do you deal with someone that's just kind of taking things off track, or just talking too long? I imagine that's just a skill and an art, but any tips there?
The good news is that most senior people, like the people that you're doing your outreach to, it's very hard to get to that title if you're verbose and long-winded and take things off track. So that's the good thing about going after executives: those people are really dialed in. No one takes a meeting off track at an executive level. Now, of course, there are sometimes people that meander. You could say, "I love this conversation. Can we park it? Because I actually want to spend another call just dedicated to that." And if that needs to happen, then of course you can run with it.
Awesome. So there's kind of two people that might be leading this. Might be the founder, if you're still doing founder sales. Could be the AE, VP of sales...
VP of sales. Yep.
Okay. Say you're not the founder and you're the VP of sales, or you're leading this as a founder, what are some signs that your salesperson is not doing a great job up to this point? What are just smells of, like, I should release everything?
I would say, what is the timeline from intro call to demo? How many conversations have happened between those two buckets, of when people advance stages in the sales pipeline? Can the salesperson articulate exactly what they are going to be demoing, why they're going to be demoing it, and how they're going to open it? The demo looks different every single time. Every single time. I don't think I've ever run a demo and it looks the same. This is like when everyone comes back to, okay, what's the scaled playbook? What's the scaled approach with this? When you're selling $100,000 minimum, right? Again, it's the same effort as selling a million dollars. So, it could be a million-dollar deal. It's hard. You're cracking some of the largest logos that every single startup goes after. You've got to be different. You've got to take a different approach. It is not cram the pitch down their throat and hope that they want to buy something.
Feels like a job AI will not replace anytime soon, from here.
Yeah, I'm not worried about AI replacing it, because there's so much about it that's just human, right? Do you vibe with this person? I've definitely taken intro calls with a person who probably did not appreciate how I ran it, and that's okay. That happens.
It's such an interesting point I've never heard before, this idea of, when you're demoing, demo as narrow a slice of the product as you can that addresses their priorities and needs, because, to your point, they may feel like, "Why do we need all this stuff? We just want this one problem solved," and that's shooting yourself in the foot.
Or let them guide you. Like, "Can it also do this?" And be like, "Oh, it's so funny you say that. We just released this." And now all of a sudden it feels like, again, it's built for them. They want to feel like it was built for them and that it's different.
And they get alpha.
And get alpha.
Okay. So step six, you call the post-demo discussion.
Yes.
Also something you say everyone ignores. Talk about that.
Yes.
Okay. So as soon as the demo closes, you are texting the woman or the gentleman or whomever has helped guide you to this point. "How do you think that went? Can I call you in like five minutes? I want a fresh debrief." They will give you... and be like, "Raw reaction. I know you haven't spoken to...
anyone. What do you think? How do you think that went? Do you think we need to go deeper with anyone before anyone solidifies everything that was said? Where do you think we lost somebody? Where do you think we did well? Is there someone we need to spend more time with? There's always someone in the organization that's going to kill a deal. There's always somebody.
You need to protect that as much as possible and make sure everyone is aligned and excited by what this is. And again, the more intel you collect on these people, because again, if for some reason someone goes quiet for two weeks or 3 weeks, you can now prompt with, "Hey, I know you guys are still in the process of thinking through if this makes sense. Do you think it's worthy if I found 15 or 20 minutes with said individual to just hear their thoughts, and maybe we can approach this a little bit more closely with how they would want to see it?"
So you're just always looking for ways this might explode and not work. And this person that you're working with, would you call them... what was the term you used for them?
Champion. The champion.
Yeah. Because the champion can also be an executive, right?
Yeah. And they're excited at this point, in theory very excited for this to work out. They're on your side. They're not trying to...
And I define champion as who is the individual that really wants this to come to life, that was there from day one, not necessarily the person that... the C-suite executive could be the one shepherding this well, but they need to make sure that the people below them are brought in.
Okay. Anything else around the demo or the post-demo discussion before we move on to the next step?
No, I think we're good.
Okay. So the next step you call identifying pilot move forward process.
The best thing you can do, assuming that you've built an incredible solution, right? If you're now this far in, you usually have something that they... allow them. Now you can control the time on, "Hey, I want you guys to go in for two to three days, these specific users." Do not put your C-level executive into the product. They're not the user. Okay, who are the users of this? I want them to experience the magic and the power of what this is. Okay, run... don't charge.
You could charge them for a pilot if it's an extended period of time, but I'd rather forego the money and do a 2 to three day pilot so that at least I can control the sales cycle a bit more. Okay? But again, if they ask for a month and there's a good reason for it, do charge for that. But I'd rather go in for two to three days and let them see if they can get the value from it. Sometimes I understand that there needs to be some level of configuration and extensive onboarding that needs to happen, but is there a sandbox where they can assess the value, even if it's not on their own data?
So this isn't yet the pilot, this is just prepping for the actual...
Correct. So there's two different pilots you can run. A pilot that does not require their data to be in the product to get the value, or a pilot that you want to charge for because they need to see some level of integration on their end for the whole product to actually work, right? I understand that those are two very technical things. Let's talk about something that they can get in two to three days and it's pretty much of a light lift. Time box it to two or three days. Don't make it two weeks. Okay, I've done this enough times to say people will go in usually for half a day and get what they need out of it. Okay, shorten your sales cycle by two weeks by doing 48 or 72 hours. Now, if you need something a bit more integrated and it's a far more technical solution, what I'd highly recommend is do it for a month or two months, charge them for it, and then use that fee that you charge them for and credit it back to them if they move forward. Okay?
If they're willing to pay, that is a huge, huge signal. Especially if you're about to put in all this work, they have no problem paying for it. It's usually probably going to come out as services anyway because they're not buying technology. They're buying the services to go through it. And also make it a credit on the back end. Don't start the relationship up shift. Start the relationship off on a good foot.
I'm definitely feeling the feeling I feel when we chat, is like I just want to find something to sell. This is really...
It's fun. It's so fun. It's literally so fun. People...
I think people read these sales books, go to these sales trainings and they try and take someone else's game and run with it. And it never works that way. No one taught me this. I was just like, "Okay, if I collect more intel than the competitive set, that will be my special sauce."
And it's more fun that way. You're building a relationship more. You're chatting more often. You're not trying to just...
Yeah. Speed rock.
It feels more real. Yeah. Okay. A couple questions here. One is this idea of the two to three day pilot. How do you convince them you only get two to three days, because that feels tough.
So I would say, here, this is what we typically do. Who are the three or four people we want to put in and assess the value from a user perspective? Okay. Make sure it's your person, right, or the person closest to the C-suite. Don't put your C-suite executive in it. They're not going to go into the product. And then two or three other people. Okay. And I want you to say, we're going to do two or three days. I'm going to onboard you each differently. We're going to do two or three different onboard sessions before those two or three days. And I want you to go in and I want you to do these three specific tasks. Be very, very thoughtful and explicit and descriptive with what you want them to do.
Okay, here's how we're going to measure success. Define that with them. Co-author that. And that's no different than the thing that's a little bit longer where you require that integration and buildout. Co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate, 99% of it,
and help them discover the magic. Release it.
Help them discover the magic. And also continue to... you might have one of those users that's like, "Oh, I didn't like it." Great. In that three-stage process, you just ask: what didn't you like? What wasn't clear? What wasn't obvious? Where did you get lost? The tighter it is, the less people get lost, the more grounded it feels and the more consistent the experience is. You don't want people having different experiences.
Okay. So, just to make it clear the steps involved here, because we've gone through, I think, three kind of around the scene.
So much. Yeah. We've gone through so much. So, we're kind of on step nine. So, there's step seven, which is identifying the pilot move forward process. A lot of people ignore just...
Who that person is and what the steps are. Then there's prep for the pilot and then there's run the pilot.
Run the pilot. Exactly.
We've kind of talked through all these things.
Now, is there anything else? Yeah.
For prep for the pilot, the one thing I want to say is, okay, before we put everyone in, let's work backwards: if this is successful, how do we get this deal through? Okay.
Ahead of time. Before doing the...
Yes. Ahead of it. I should have clarified that this is all before the people's pilots start. This is in the pre-pilot stage. Okay. Assuming, fingers crossed, a successful pilot, which I feel confident it's going to be. One is, when do we want to get signatures on these papers? Let's work backwards from there. Do we think we can get this closed by the end of next month? Yes, I do. Great. Who needs to be involved in that? Do you have a procurement lead that should be educated in this process? And they might say, let's wait till after the pilot. Totally, but push them a little bit. Again, you're project managing it. Is there a security lead we should be working with to run due diligence on the product? Is there someone in legal, or is there a way for me to draft the paper to make this make sense? Now, the one thing I'm going to take a step back on is you would have already gone through pricing discussions with them post-demo.
Okay, try to hold out on talking about pricing until post-demo, because they might assume, "Oh, this is three times what I'm spending," and not know why it's three times, right? Because there's all these other people that might not have been involved in those initial discussions. Talk through pricing post-pilot once everyone's excited.
Post-pilot or post-demo?
Right. Post-demo. I apologize.
Okay, cool. Yeah.
So, and so you basically just kind of tell them, we'll figure out pricing once we understand what you're looking for.
This is in the pre-pilot stage. Talk about pricing.
Okay. Now, if they're this far along, if they're really concerned about pricing, they would have brought it up by now, right? So, these are the little cues, like, "Okay, I think I could probably push them a little bit here, right?" Or go a little bit further. Two is, if they ask and they push, give them a ballpark. "Well, it depends, but let's say it's somewhere between 150 and 250, and there's a lot of dependence on that," right? So, you can give them a ballpark, but work with your champion to say, "Listen, here's what the price is. I know you know why we price it this way. Before you put this in front of anybody, how are you going to make the case?" Right? Where are you going to cut? How are you going to defend it? How can I build out a slide to defend this for you and show you the ROI? Let them. They will tell you. You don't have to go blind into it.
And then if they come and then say, "Okay," and if they push back and they're like, "Listen, I don't know if I can go to bat for this," be like, "I hear you. Let's work on this together. What do you feel comfortable going to bat with? And can we do a step up for year two to get to the actual full value of what we know we charge?"
And do you include the slide or the price in the demo, or is that a post-demo conversation? If they push you to do it, give a ballpark,
but do pricing one-on-one with the individual you've been working with
because they will help. They might say, "Okay, I think we're all aligned." This is what's usually going to happen. There's three answers. We're all aligned. I'm not too concerned about this. I don't know if I feel comfortable going to bat with this number. That's when you say, "Okay, I hear you. Let's take a step back. Let's figure out how to make this work."
Don't say you're going to discount. Don't throw out numbers. Be like, "I need your help to tell me how to make this work." Now, this is the one part where you want to put it on them, because they might come back and say, "Is there any way we can cut 20K?" And you're like, "Oh, I would have gone much lower than that," right? You don't want to negotiate with yourself. But work with them. You've gotten to this point. You've shown so many people. Everyone's excited. This is when you know you can win them over through the co-authorship. And remember, you can always do the full value in year two and sign a two-year deal.
Awesome. The expand.
Okay. So, in the pilot step, how many people do you give access to the pilot? Any advice there?
Three. Three to four.
Okay. So, very small.
Very small. Very tight. Who are the power users? Who are the people that are going to be in on a daily level? You don't want everyone in there. You want it to feel like they're buying into it too, not the same people, but you do want that one individual that's been giving you all this intel to be part of the pilot, because you want them to get you prepped for everything.
So before we get to the next step, which is post-pilot discussion and session, I imagine many products, especially today, just take a lot of integration work and data ingestion and all that stuff, this whole FDE emergence. Thoughts there, if your product is just like, "Wow, it's going to take us a month to even get you onboarded"?
And that's when we talked about those two different pilots. There's like, "Hey, we can show you the value in two to three days," or it's the "Hey, we have to show you the value in 30 days." For a 30-day value, charge and credit it back to them, but know that your sales cycle is going to probably be a month longer because of that. But that's okay because you're probably charging more anyway.
Got it. And just do the work to integrate enough to make it...
Your price should be predicated on your sales cycle, right? If you can get a deal done in 90 days for 100K, do that all the time.
Right. If it takes nine months to get a deal done, you probably should be charging 250, 300K.
What are your thoughts on forward deployed engineers as a part of this process, just as a role?
My opinions sway back and forth. Is a forward deployed engineer there because the product's super hard to navigate, or is it there because you're taking the work off their plate? I think people use them. I'm all about it if it's taking the work off their plate and accelerating and controlling the situation, all day every day. But are you using a forward deployed engineer because your product's so gnarly and hard to do that they can't do it on their own? It's a bad sign.
Yeah.
Yeah. I feel like the original idea of forward deployed engineer, and the Palantir guys talk about this, the original idea was they work inside of your company building custom software for you to solve your problems, and then they figure out how to make that a broad product they can sell to other people.
Totally. And I think that an FDE is great for an expansion, for a land on... okay, if you're talking about a Palantir where it's much more complex, I understand why they did that. Right. But they're also charging multi-million dollar deals.
That's right.
Right. So the business model structure supports that. If you're selling a $100,000 deal and you're pulling a forward deployed engineer, your economics are going to get messy. You will not make money if you have a full-time engineer salesperson sitting there working on this.
And I also know there's a lot of folks in account management whose job is to service and expand and upsell, and they just take on the title of FDE, so they're just another salesperson.
Yeah, it's just a nice... Yeah, it's a cool title. I think the Palantir people called FDEs at most companies "sparkling sales engineers."
That's awesome.
Yeah.
Okay. Anything else on the pilot, up to the pilot step, before we get to the post session?
Yeah, I think because now you've talked about the timeline to, if this is successful, what does that look like? Again, you want to run this before you put everyone in it, because you might want to push out the pilot. If they're like, "Hey, listen, this is probably going to be another quarter." Well, put the people in the pilot now, because now you've lost all the... you need the momentum to continue. You need the steps to happen. So, use that: "Hey, if this is a successful pilot, how far out are we from a commitment from you guys?"
Oh, I see. Commitment. So, there's the commitment, and also just... which is equivalent to rolling it out to the company. That's exactly...
If they're not ready in a month to roll this out, if this is a huge success, then wait on doing...
Correct. Yeah.
Awesome. Because you're saying you may lose that momentum and
Yeah. You've already exhausted all the stages. You don't want to do that. You want the stages to align with how they're thinking, but you want to project manage as tightly as you can. And some of it's out of your control, but yeah.
And yeah, it's not like you can push them to deploy it broadly. That's a thing that is probably very hard to shift. So, so yeah, so understanding that and working with that seems really important. Okay. So, step 10. And again, as you pointed out at the beginning, most people think the sales process is five steps. And we're already in step 10, and we're not even done.
And you made this point actually before we started recording that you haven't touched on that I think is important to share, this idea that these five steps kind of emerged out of a CRM pipeline kind of check thing. Talk a bit about that.
Yeah, so everyone knows the traditional five steps. Intro, demo, proposal, contracting, and then closed won or closed lost, right? Those are the typical, or maybe there's some variation of that. That's not how you run the sales. Those are buckets to understand a weighted forecast, right? A proposal or something midfunnel might be weighted at 50% of the deal value for the pipeline. Something in contracting might be weighted at 80% and something in intro might be weighted at 10%. That's what those stages are for. That's not the stages you take a client through. Those are just the broad buckets.
And I think a lot of people use those buckets to say, okay, there's about five different meetings that need to happen, when it's like, no, there's three meetings, maybe up to five meetings in each of those buckets that are critical to get the deal done. Now, we're still speaking at it at a very macro level. Obviously selling a million-dollar deal, you want to have more of those upfront meetings. And you want to make sure you know who the executive sponsor is and all that. You always want to know who the executive sponsor is, but for a 100k deal, you probably can accelerate it a little faster. Again, ensuring that they're qualified.
And you've worked with a lot of founders and salespeople over the years. What percentage do you think are just doing it wrong in that way and treating it like this five-step process?
90%.
Wow.
Yeah. Because enterprise sales is mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process.
Amazing. Okay, let's keep going. Step 10, post-pilot session.
Yes. You can send a survey. They might want to send a survey. Get the intel, or one-on-one to each of these users and say, "Hey," or let your champion, I mean, there's a few ways you can do this. Or you can have your champion internally discuss and say, "Hey, how was that?" Okay, you need to make sure that you are mirroring their experience, right? From a technical perspective, how much time did they spend in the product? Did they run into any bugs? What were they using the most of?
Because you need to be prepared going into that call to say, "Hey, I know we gave everyone those three things, but most people only spent it on two." Why? And that might be okay, but you don't want them to be like, "Oh, well, you know, we wish it did this." Well, yeah, but no one spent time on that. We do do that, but no one spent time on that. So, you just need to control also that you're capturing what they did in those pilots and making sure that you're syncing up.
Or you could go to your champion and be like, "Hey, I know so and so logged in for 15 minutes today. They didn't get past step one." Don't tell them what they're doing. You shouldn't even be, but they didn't get past step one. "Can you check in on them and make sure they're having a good experience?" Use your champion to, again, they've invested so much time into you, guide them with where they should be focused as well. Because at the end of the day, getting a deal done at the enterprise, it is set up to have as much friction as possible, right? There's people that will kill the deal, then you got to deal with procurement, then you got to deal with legal, then you got to deal with finding the executive sponsor, right, which usually comes in the very top of the funnel. But there's so much friction to get a deal done. The project management and the individual on the inside, that's your key.
So funny. So many ways it could all fall apart.
What I was going to say is it feels like many people would naturally, they want to avoid confrontation. They won't want to say, we don't want this. They're going to probably be like, it's fine. It's good. It's good. Oh yeah. Everything's...
Like PCs.
That's right. That's right. And so it feels like a lot of this process is to pull out, okay, here's the concern. Here's the problem. Are there any other signs of, okay, they're actually not interested and this is not going well and I need to really...
This is why your internal champion is so important. When they go quiet on you, that's when you know. That's why this individual, and listen, this individual is going to, if they've spent enough time with you, they will call you and be like, "Listen, if I'm reading the tea leaves, we should sit on this for a minute. Let's pick this back up." That's why having someone on the inside is so, so, so critical.
And yeah, the easier approach is just to stop responding and just hope that the salesperson understands, or a little not excited.
Oh man. Okay. What are the benchmarks for how often you get through each of these stages? You mentioned a few, just like, yeah, from demo to the stage.
Usually once something is qualified, meaning you're speaking to the right person, they are excited by the alpha, they admit that there's change that needs to happen. Notice I didn't say problem, but change. People get so fixated on problems, which are important. They are important, but everyone speaks to the same problem and it commoditizes you, which is why I don't like to overly emphasize it. The win rate for enterprise, a good healthy win rate, is actually probably going to surprise you. It's not 50%. Meaning of all sales qualified leads or opportunities, a healthy win rate is usually around 30 to 35%.
From qualified lead to...
Qualified signed contract.
Meaning you speak to 100, you're closing anywhere between 30 to 35, maybe slightly less, maybe 25 to 30. That seems high actually. Yeah, somewhere between 25 and 35%. Why? If your win rate is higher than that, your price is too low. There's a lot of part of the market that's just not in a maturity perspective to take you on. And that's healthy, right? Those are all the chasms.
And the implication here is it's better off keeping your price high than winning more often.
Yes. Because the market talks too. The worst thing you can do is charge somebody's friend 50 and somebody else 500k. They talk. People, the market talks. You have to assume that.
Yeah. I'm in a lot of WhatsApp groups with founders and they do exactly that. What kind of deal do you get for this product?
That's exactly right. So assume the market talks, especially at the corporate executive level.
And someone might just not be ready yet. And that's okay. The amount of deals that boomerang a year later of the ones that have lost, that's probably another 25%. So it is totally normal and natural for deals to not advance, right? But a healthy win rate in the enterprise is typically, I would say, between 25 and 35%.
Okay, that is incredibly helpful to people. I know. How about key stages along the way, just percentage drop-off and...
So it's usually from qualified lead to, you're coming out of demo, it's probably, you'd lose half, and then...
Out of demo.
Out of demo. Yeah. And then...
Post demo. Yeah. That gets you to 30%. So from demo to, what was that step that you...
From demo to, the more you move down, the less those numbers, the less wide those numbers. So like...
Okay.
So let's say if you speak to, and you're doing a really good job targeting the right people, maybe 70, 50% of those people move to a qualified lead, or 50 to 75% move to qualified lead. Of that, then another half move to demo, and then from there another quarter advance beyond that. Once you're in the bottom of funnel, you usually don't lose too much from there, if you're doing good deal qualification.
So say you're at the pilot stage, what percentage should you expect? Drop-off and...
20.
80% succeed post pilot.
Correct. Yeah. Okay. Amazing. I find that. Yeah.
Okay. So, if you're below that, something's wrong with your pilot.
Yeah. Or you're not qualifying clearly, or... I see. Yeah.
You're almost doing too good a job convincing them this is the thing for them.
Correct. And the product's not there. Correct. So, yeah, that's where, and again, smart buyers always want to do a pilot. So, just have it part of your process.
Okay, there's four more steps to go before you're done, before the money's wired. Okay. So, step 11, papering prep, setting timeline for procurement.
Yes. So, you have now spoken pre-pilot about the timeline of what we're reverse engineering. Now, you're going to document it in an email so that the champion that you're working with can forward that to procurement to say, "Hey, here's what we agreed to. Here's the pricing that's predicated on us getting this signed by this date. Here's the," they give them something, "here's the kicker they're going to give us if we get to this date." There's always got to be a reason to create urgency.
And then what you want to do is say, here's our paper. Send a Word document. Do not send a PDF, because they're going to always redline. Always send a Word document of your paper and ask the question: do you want to use our paper? Here's a Word doc version. Or do you want to lift from it, and do you want to use your paper? It might be a lot faster to use their paper. That's why you give them the option. And that's why the timing isn't there, because they might say, "Well, in order for us to hit that time, we got to use our paper."
And it's not Google Docs. It's Word, like Microsoft Office...
Microsoft Word. Yeah. Most of these people can't access Google Docs. But yes.
And so this says post-pilot, feels like it's gone well. You're saying the next step is, here's the contract basically, get that to procurement that early.
And again, your internal champion is, you're working from N minus one from the executive sponsor, or it's the executive sponsor themselves. You wouldn't have made it, they're not going to put their team into a pilot if it doesn't have legs.
And an implication here is procurement is a way that your deal might still die even if people internally love your product.
Correct. If you get sent to procurement. So here's something interesting a lot of people don't realize: people will use procurement as the excuse to not want to give you the bad feedback. "Oh, I got to go talk." "Oh, it's procurement." "It's lost in procurement," or ah, right? Very easy to blame procurement.
Usually, procurement is a 30-day process between the back and forth on the legal, the papering. Procurement's job is not to kill the deal. It's just to make sure that it is aligned with how they need to buy. That's their job. Procurement is the only person that can get you paid. Do not start any work till you go through procurement. Business unit leaders can't just pay you. That needs to come from the finance team who pulls from the budget. So be very careful, don't start any work until obviously the papers are signed.
Start work meaning implementing, rolling out, people onboarding. Got it. Got it. Got it.
Okay. Amazing. Okay. So that's step 11. Papering prep. Setting timeline for procurement. Kind of getting on board with what is it going to take to sign by this date? Here's a little gift you'll get if you do it by this date, free month or whatever. Okay. Step 12, papering review.
Yes. The best thing you can do is, they're going to send you back redlines. No question. If the redlines are extensive, okay, go ahead and accept the things that are easy. If the redlines are extensive, see if you can get legal on a call live and just talk through them. That will accelerate your sales cycle.
Versus a bunch of back and forth.
A bunch of back and forth. Get them on a call. Be like, "Hey, everything, we're 80% of the way there. I have a few questions based off of your redline. Can we jump on a live call and just go through them?" Focus on the things that are going to impact the business and push in on those. Let the other stuff go if it's not super important. Obviously, have a lawyer look at it from your side. You're dealing with a commercial lawyer, commercial legal team, have a lawyer look at their redlines.
I imagine most companies have a legal counsel.
Yes, I would hope. I would hope so. Yes.
Okay, cool. So, paper review. So, that's reviewing basically. It's interesting, called the paper. Is there a more technical term for that? Like the...
Contract. I say paper. That's corpo language. Paper.
So interesting. Okay. Papering review. Okay. Step 13. Papering procurement process.
Yes. So this is where, we kind of talked about this. We kind of merged that conversation. This is when you are getting the procurement lead and the legal lead on a live call to work through the questions or the things you cannot accept. Now remember, if they give you their paper, there's going to be a lot in there that you're going to need to...
Redline.
Redline. They're expecting that. They're just giving you the kitchen sink, right? If they ask for $10 million of liability insurance as a smaller company, you can push back and be like, "Listen, your exposure with what we're doing is not that high." Or maybe it might be and you need that, but you know, they're going to give you the kitchen sink. Know that it's all negotiable.
But pick battles. Pick your battles.
Yeah. Don't be afraid the deal will fall apart if you see something in there.
At this point, the deal will not fall apart. You just need to work closely with them to make sure they understand where you're coming from. That's more what it is.
Okay. Okay. And the final step, signature. Tada.
Yep.
Anything special there other than signing?
No, this is the really exciting part, which is just figuring out who the signatory is before it goes routed for signature, so that your, make sure your internal client knows, you know, because sometimes it's the CFO. It's not the executive sponsor. And you just want to make sure everyone knows who that individual is, because if there's a delay, you just want to make sure they get pinged.
Damn, we did it, Jen. We did it. We got through all the steps. We just signed a massive contract. Congratulations. Let's go. Steak dinner, champagne. I don't know what salespeople do when they close a deal. Ding a bell. There's bells often.
You know what we do? Okay, what's the next one? That's it. Because you are in sales. You're only as good as your pipeline.
So fun. It must be the best feeling after all this work.
It is. But then you're like, "Oh, now..." Literally the feels is like 5 minutes and you're back to work.
Yeah. And I imagine part of this is also how do we expand this deal?
100%.
Is there anything there, just real quick, just how to start thinking about where this goes once the deal is signed?
Yeah. And this is where I think the expansion comes in. You either know the products that they can expand into, like you've been through this journey before and that's pretty straightforward. But
If you are early in the journey and you're closing your first 10 enterprise customers, you need the founder involved once these people are in to understand what part of the product is custom to what these people need, and do we want to build out, you know, do we want to charge for services? Again, here's the other thing too: services. And I know every company is an ARR, recurring revenue focus, but services is still the largest line item in budgets.
And so you're saying it's okay to offer services.
Yes. Yes.
Yeah.
Yeah. This has come up a number of times, I think with Jason Lemkin and you, just like the increasing, like there's a rise in services being a part of software companies.
To buy. It's what they know how to buy. They're so used to it. Consultants, lawyers, you name it. The budget, there's always budget for services.
Yeah. We talked about this last time, so we won't get too deep into it. Something else I wanted to ask you kind of at the end here. Say you're a buyer and you're talking to Jen and you're just not sure this is a fit. You don't want to disappoint. You don't want to drag you along. What are some things that people buying software products, working with a salesperson, how should they communicate? What should they be saying to kind of avoid disappointment?
Yeah, I would say as soon as humanly possible, explain why the timing is not right. It usually comes down to timing or why they're not mature enough to be able to be in a position to... It's interesting, your organization and the team has to be structured in a way to bring on the technology. Like there's a maturity you have to go through, and I know we talked about this before where sometimes it's easier to sell the service first and then do the technology and counsel them towards the technology. But if your sales maturity in the enterprise is further down the road, you want to start with selling the technology versus the services.
And if you talk about how it's not the right timing or not mature, I imagine the salesperson will try to prod you and push you to see if maybe you're not. So, it's okay to just tell them what you think.
It's, you know, what you can get. I've had clients say to me like, "Hey, I don't know if we're in a position to do this." And I've straight up said to them, "You are a liability not closing this gap." And sometimes they just need to be like... Again, you need to know if you're in a position to be able to say that.
Yeah.
But like, listen—
I know you need this.
I know you need this. I'm not accepting no as an answer. How do we figure this out together? Because again, use the intel they've given you towards that.
And interestingly, you're talking to a lot of their competitors, and you would think you have insight into, okay, here's what everyone else is doing in this space.
Yeah, exactly. Or like, "Hey, listen. On our first two calls, you told me how important this is. Did that change?" "No, we're just in a weird spot." I'd be like, "Okay, listen. Here's what we're going to do. Let's start it a little bit smaller. Let's get in. You admitted that this is something that you guys need. I know that we are going to crush it for you. I don't want X to get in the way of that." And then there's obviously going to be the cases where it's just not the right time. Like they might be going through an acquisition, right? And bringing on net new vendors is just not a priority right now. You just have to respect that too.
I love how this whole process... A lot of listeners of this podcast are product managers, product people. It just feels very producty and product manager in terms of the organization and the step by step and just staying on top of all these little things. It's so interesting how you don't think sales and product management are at all alike, but—
But they're so similar, and it's just like you being human, like the way a PM tries to understand what your pain points are. We're here to solve them.
Yeah, unexpected. We did it, Jen. We did it. We went through it all. Is there anything else? Anything else we haven't touched on? Anything else you want to, I don't know, leave listeners with before we wrap up?
We gave them a lot.
We did it, which was the goal. Just the right amount.
Yeah.
Yeah.
I'm excited for... Oh, I was gonna say, I love that AI, I don't think it came up, maybe one time in this conversation. Very rare these days in podcasts, which I love.
Well, it's interesting, so many people will create AI reports that they can send to their clients, or AI imagery, or, I don't know, you name your flavor. And it's like, anyone can do that. It just feels salesy.
What's your alpha? It always comes back to that.
Exactly.
And I know you talked about this last time, just craft your own email and text. Don't—
Don't use the boilerplate. Don't use your AI.
Emails are living and breathing. I swear to God that people can read you saying the email out loud.
Yeah. Okay, Jen.
This is awesome.
This was amazing, everything I wanted it to be. I'm excited for, not to talk about it, but just the AI summary of this especially. That's just going to be like step one here.
Yeah.
Final questions? Anything you want to plug? Anywhere you want to point people to, and how can listeners be useful to you?
Let me know if anyone has questions. I'm more than happy to go deeper into this. I would say, here's a plug: if anyone is interested in enterprise sales, we are actively hiring, and I will teach you everything I know.
Wow. And this is at State Affairs.
This is at State Affairs.
Holy... What an opportunity. Yeah. So there's multiple roles, not just one.
Multiple roles. Yeah.
Wow. You'll be paid to learn from Jen directly.
Yes. I will teach you everything I know.
Whoa. Okay, cool. We'll link to the job descriptions in the description if you want to check that out.
Awesome.
Amazing. Jen, thank you so much for being here.
Lenny, this was awesome.
It's awesome. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
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