Jason T. Ray on Decisive Leadership: Why Indecision Costs Job Shops More Than a Wrong Call

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Overview

Jason T. Ray, co-founder and CEO of Paperless Parts, is a recurring guest on Manufacturing Happy Hour. He has appeared roughly every hundred episodes, including around episode 20 and again at episode 120. This conversation was recorded in person in late April 2025 at the Tip Tap Room in Boston, which Ray describes as the restaurant where he and his wife went on more dates than anywhere else in the city. The theme that runs through the whole discussion is decisiveness. Ray's position is that during uncertain periods, such as tariffs, reshoring hype, CMMC deadlines, or AI, the leaders who hesitate fall behind. His summary: experienced CEOs usually already know the right long-term decision, and the real question is whether they have the conviction to get through the short term while it pays off.

25 min read

What Paperless Parts does, and why it stopped trying to do everything

Asked to describe his company as he would over a beer, Ray first says the answer keeps evolving. Paperless Parts builds a front-office platform for job shops and contract manufacturers. It covers estimating, managing RFQs, sending quotes, and collaborating securely with customers and outside vendors. He organizes the platform around four pillars.

Workflows. In Ray's account, estimating has become "a team sport." A shop used to rely on one person with 30 years of tribal knowledge who priced parts by gut feel, a feel built partly from living with past mistakes. Ray sees more shops now pulling expertise from each area of the shop into estimating, so Paperless Parts built collaboration tools for a centralized quoting process.

Costing and pricing automation. Ray calls this the company's core intellectual property: analyzing 3D models and 2D prints and automating as much as possible so that pricing is consistent. His co-founder describes it as "guardrails," meaning automated limits that let estimators move fast "without driving off the road."

Customer experience. Ray describes the quote as often being a shop's first impression. The goal is a quote that arrives quickly, communicates clearly, and offers different buying options, creating "the biggest strike zone you can to win that work."

APIs and connectivity. Paperless Parts integrates with ERP, CAD/CAM, and CRM systems. Ray says this pillar comes from being honest about how hard software is to build. Early on he had what he calls a "wet behind the ears founder mentality" and imagined building everything in a shop from front to back. He later concluded that doing so does customers a disservice, because a company can't do all of it well and ends up making compromises. The company decided to "nail this piece of the value stream" and make it easy to connect with everything else.

Is the skills gap still a leadership gap?

The host, Chris, says he regularly quotes a line from their previous interview in his keynotes. Ray had argued that when a problem has persisted for as long as the manufacturing skills gap has, it may really be a leadership gap. Asked whether that gap still exists, Ray says it is closing, though some gap will always remain as businesses change hands.

He gives the main credit to how much information now reaches shop owners. Owners used to have to seek out thought leadership themselves, by joining organizations like NTMA or finding a local manufacturers' network where peers were willing to share ideas. Ray says manufacturing has never been "so online," with podcasts, articles, and other resources delivering best-in-class information directly. When he asks his customer advisory board what they read and listen to, the answer used to be paging through The Fabricator or Modern Machine Shop now and then. Ray calls that good content, but he says today's content is more accessible, and owners are investing time in consuming it and putting it into practice.

He sees a newer problem, which he calls an experience gap. As owners exit, people who have never run a job shop are taking over. Ray describes job shops and contract manufacturers under about $25 million in revenue as "a unique beast": extremely complicated, always changing, and unlike other manufacturing environments. Leaders from general manufacturing sometimes assume they can run one of these shops, or a roll-up of several, using the lean and operations skills they already have. Ray cites Mike Tyson's line that everybody has a plan until they get punched in the mouth, and says this industry "is definitely a punch in the mouth sometimes."

Young people in positions of responsibility

Chris asks what else leaders are doing to close the gap. Ray says owners are increasingly giving real responsibility to people in their early or mid-twenties, often college-educated professionals. Before, many owners would have refused, reasoning that it took them until age 40 to earn that kind of authority. Ray argues that new ideas, plus the information now available, plus actual authority to make decisions, produce good outcomes.

Chris adds that early in his own sales career he was handed the accounts nobody else wanted. He sees recent graduates, including those coming out of trade school, as having fresh knowledge, ambition, and energy that deserve more responsibility.

Ray then describes a second effect of the flow of information, which he calls "softening the ground." It is hard for an owner to introduce an idea such as a profit-sharing incentive model or a new approach to team building when the workforce has never heard of it. It is much easier when employees have already encountered the same ideas and see themselves as working in an industry many people consider "very sexy and very cool." Ray says the people attending Paperless Parts webinars and clicking on its content are not only owners. They come from across the shop.

Leading through crisis: "I may be wrong, but I'm never in doubt"

The conversation moves to tariffs, which manufacturers were trying to navigate at the time of recording. Chris notes that COVID was a similar moment and that more will follow, and he asks how to lead through unpredictable times. He points Ray back to his Navy background.

Ray repeats something his stepfather told him when he entered the military: "I may be wrong, but I'm never in doubt." In Ray's view, uncertainty pushes leaders toward indecision. Indecision wastes people's time and can "shatter your team's confidence" in the leader's ability to make calls. The most successful crisis leaders he has seen act decisively. He clarifies that this does not mean sticking with a wrong decision until the company fails. It means picking a direction and following it until data or signals show it is wrong, then pivoting without hesitation.

He cites Elon Musk, who, as Ray recounts it, said in the early days of Tesla and SpaceX that the average Fortune 500 CEO makes one major decision every six months while Musk made one a month. Ray explains the reasoning: over six months, the faster leader makes six decisions. Even if three are wrong, three months remain to make three right ones. That leader ends the period with at least three confident, correct decisions, while the typical leader has made one.

His Navy example comes from leaving port in Dubai. The ship was moving through fog when the crew looked over the side and saw the bottom, which Ray says is not something you ever want to see in the Navy. They called "all back" and reversed engines. When the fog cleared, there was an island directly ahead that the ship would have "T-boned." It was new and not on the map. Ray connects it to land reclamation in the region funded by oil money. The point, he says, is that you make the decisive call in the moment, in this case reverse to avoid running aground, and then reassess and set a new course. You don't leave the ship going backwards. People looking to a leader are looking for decisions, and part of that is being willing to say, in effect, "I was wrong, not because I'm stupid, but because we didn't have all the data, and now we can pivot."

What job shops should watch, and the cost of waiting

Applied to job shops, Ray says the industry faces both massive tariff uncertainty and "an enormous hype cycle" around reshoring. He mentions surveys, attributing one to McKinsey, projecting half a trillion dollars of work returning to the US, and other agencies estimating it would take four years just to tool up for that work. Owners have to work out what these conflicting signals mean for their own business.

The leading indicators he would track as a shop owner are RFQ volume, broken out by existing customers and new ones. He would also go to every existing customer to understand their thinking. The question he would ask is less "will you keep ordering from me" and more "how can we be the best partner to you through this?" He would put his cards on the table about available capacity. Making these decisions in isolation, he says, "will do you no good."

His second point concerns long-term conviction. Many owners know the right five-year decision, such as expanding the shop, building a new building, or adding machines, but get nervous and decide to wait. Ray's argument turns on lead times. Every capacity investment, whether production, estimating, or sales, takes time to complete. A building started today won't be finished for a year. Owners who wait for a signal instead of trusting 30 years of experience end up deciding too late. Then the orders or RFQs arrive and they lack the capacity to handle them. The people he has seen succeed through uncertainty are those who don't waver on decisions they know are right, whether that means expanding capacity, training the team, or investing in a fix for a known problem. They are better positioned when the pendulum swings back, which, he says, it always does.

His example is his co-founder Jay Jacobs, who built Rapid. In 2008, when everyone was tightening spending, Jacobs bought a machine shop, betting that prototype machining work would come back strongly and wanting to be ready to catch it. Chris suggests the purchase was probably a bargain, and Ray agrees: being decisive when others hesitate lets you capture those deals.

Data versus information

Ray adds a distinction. Manufacturing, in his view, may have more data than any other industry, but there is a large gap between data and information. Data sitting unstructured in an ERP, a CRM, and email, and never analyzed, doesn't become information. He thinks many shops conflate the two and believe they run on data when they don't.

He uses RFQ traffic as the example. If RFQs arrive in five different inboxes and nobody logs who sent them, how many line items and what quantities they contain, how fast they're coming, and what the turnaround times are, the shop has scattered data. It cannot tell, for example, that one sector's RFQ traffic is rising as semiconductor work returns to the US while another has slowed sharply. Without that pulse, Ray says, owners can't make informed decisions, and that is what leads to indecision. Chris notes that AI has come up on the show as one tool that may help turn data into information.

CMMC: what to demand from software vendors

Chris recalls that CMMC was "coming" in their first conversation, delayed in the second, and is now here. He summarizes it as the security requirement shops must meet to do government work. Ray first gives context: his customers in the defense industrial base "have never been busier," with a wave of funded defense-tech startups, such as Anduril.

His core advice is that shops need to know the right questions to ask. They will rely on software vendors and managed service providers, but they have to be able to cut through the noise. He says vendors often claim "we're on GovCloud," and that claim "means nothing." A software solution can sit on GovCloud and still not allow its customers to reach CMMC compliance.

Ray lays out his view of the requirements. Cloud-based manufacturing software, which describes most modern tools, makes the vendor a cloud service provider, and in his account such providers must meet NIST SP 800-53. He says that when a software company talks about NIST 800-171 in this context, it is "the first indication that they actually don't know what they're doing," because that is not the standard that applies to the vendor. He tells manufacturers they have the right to demand two documents from every vendor: an attestation letter, which shows the vendor has been audited, and a site security plan, which shows how the vendor is addressing what the audit found. The risk he wants shops to avoid is spending heavily on compliance inside their own four walls and then failing the audit because a vendor fell short.

On whether CMMC will actually be enforced, Ray says there has been a lot of talk that it might be cut or removed from the budget. He reports that about two weeks before the recording, the DoD CIO told a conference that the train is coming and everyone had better get on board, that there had been plenty of time, and that the department would not pull punches with primes whose supply chains weren't compliant. The audience, he says, included supply chain heads from GE Aerospace, Northrop Grumman, Raytheon, and Lockheed Martin. His conclusion is that "it all rolls downhill." Shops should make a decisive choice either way: decide not to take on ITAR or CUI work, or commit to compliance to win aerospace and defense business, and in that case push their vendors to prove they'll support it.

The tiptoeing, and a lost Northrop RFQ

Asked whether shops are actually deciding, Ray says there is "a little bit of tiptoeing." Some were waiting to see whether the program would be cut, which he believes is decisively not happening. Others are waiting to see whether something like student loan relief will appear: a government subsidy, or OEMs deciding to pay for their suppliers' audits.

He frames the choice as a comparison. If compliance costs $70,000, the most a subsidy could ever return is $70,000. Not complying carries fines that he describes as now uncapped. And there is the work a shop gives up. He tells of a customer who had to walk away from a large Northrop government RFQ because they weren't CMMC certified. It was a chance to land a new customer and potentially generational long-term-agreement (LTA) work. The owner told Ray they had delayed while waiting to see what would happen. The RFQ stated that CMMC compliance was required even to access it, and they didn't get the work.

Chris calls it a simple ROI calculation. Ray picks up on the term. He finds that very few manufacturers know how to calculate ROI outside of a machine purchase. They can reason well about how many hours a machine will run, how fast it will cut chips, and how much extra revenue, perhaps $250,000, it will bring. For less tangible investments they stall on whether the benefit will really materialize. His advice: if you know there's a problem, you have a way to solve it, and you've done the work to evaluate the solution, "pull the trigger."

AI: pick the low-hanging fruit and use it as a thought partner

On whether job shop leaders are focused on the right things with AI or caught up in hype, Ray says everyone is talking about it, as they must. Some are wasting time on problems the technology can't yet solve. He compares it to an orange tree with no ladder: some people struggle to climb for the fruit at the top when they could pick what hangs within reach. His advice is to deliberately capture the low-hanging fruit and use the technology for what it does well today.

In his view, AI today will not produce estimates for you or program a part for you, though it might help. It can help draft a more effective email to a customer, organize data, and help you understand what is happening in an industry. The most effective users he sees treat it as a thought partner. His example: tell the AI you run a job shop with 40% aerospace and defense work, 20% semiconductors, and the rest a mix of medical devices, industrial work, and "cats and dogs," then ask what it would be thinking about if it ran that shop. It might come back with tariff considerations and five variables to watch, and you can keep questioning it, about specific materials for example, and use it as a counterbalance that helps you develop your thinking faster.

He compares it to the move from calculating by hand to using a calculator. The calculator didn't remove the need to know what to enter. Likewise, the questions and prompts you give AI determine the quality of what you get back.

"Your business is making parts": the Lego lesson

Ray adds a point about partners, drawing on a favorite case study from his MBA. As he tells it, Lego expanded into theme parks, restaurants, movies, and "Lego everything," was losing money in many divisions, and was going under. A new CEO slammed a plastic brick on the table and declared that this was the business. The company divested everything else, returned to its core high-margin product, and in Ray's telling grew exponentially from there.

The lesson he draws is that a contract manufacturer's business is making parts, not software. Building your own ERP or rigging up AI to create your own scheduling boards may be appealing, but the total cost of ownership is far higher. He says prospects who ended a sales cycle years ago by deciding to build their own solution or stitch tools together to replicate what they saw in demos come back at what he describes as almost a 100% close rate, because building scalable, secure software is so hard. Just as a job shop wouldn't build its own CNC machine, it shouldn't build its own software. Shops should become good at identifying the best partners, not at integrating emerging technologies themselves.

He describes that integration work as his job. He says there are clear cases of software companies adding AI without anticipating the computation and server costs and then having to double their prices. Ray says Paperless Parts is not changing its pricing as it adds AI, because it is doing so intentionally.

Scaling from prototype to production: the shift math

Chris asks how job shops can scale, particularly from prototype to production. Ray says the question comes up often as customers move from one shift to two or three. They land what he calls "shift-making opportunities" and ask how to price them, because all their pricing assumes equipment running eight hours a day, five days a week, with overhead (perhaps 30%) allocated to those hours.

He walks through an example. A laser cutter costs $1 million, and the owner wants to pay it off in five years, so it must generate at least $200,000 a year. Add roughly $50,000 a year for cost of capital and maintenance, and the machine needs about $250,000 a year. One shift without lights-out running gives at most 2,000 hours a year at 100% utilization, which nobody achieves. Ray uses 1,200 hours, about 60%, which he says some might call overly conservative but he doesn't think is. Recovering $250,000 over 1,200 hours yields a laser rate of roughly $200 an hour. He adds, "I think that math is right."

The dilemma is what happens when a shop is about to double capacity with a second shift. Should it lower prices for all existing customers, or only for the shift-making job? Ray says this is where many owners get stuck in the move to production. Production buyers expect high asset utilization and return on assets. They expect the laser to run 20 hours a day, and if it doesn't, they take a "shame on you" attitude. Shops then hear that they're too expensive and don't understand why. Ray says it comes back to understanding this math.

His view is that adding shifts is the cheapest way to scale, but he stresses that cheap is not easy. Scaling in manufacturing is human- and capital-intensive. Still, doubling capacity on one shift means buying many more machines, while running the same machines twice as long gives a shop a chance. He sees owners experimenting with schedules: four 10-hour days, which frees Friday through Sunday for a separate crew working three 12-hour shifts, or hours like 10 a.m. to 10 p.m. for parents who handle school drop-off. Structuring shifts around people's lives, he says, helps attract the talent needed to staff them.

Getting the team to buy into growth

Asked how to bring the rest of the team along, Ray says every decision requires buy-in and points to "what's in it for me." The underlying cultural message he describes is that the business is everyone's ship, or "life raft": if it sinks, all the jobs go away, so everyone should want it to be better. Beyond that, a better business can mean higher pay, easier or more interesting work, new responsibilities and skills, or something as simple as a weekly team lunch.

He says he sees these approaches working. The old model was an owner checking the bank balance at year's end and handing out Christmas checks with a handshake. More owners now see that as a lost opportunity to build momentum and buy-in throughout the year, sharing both wins and downsides.

Citing Jocko Willink's ideas on ownership and retrospectives, Ray says the best shops sit down with the worst parts they made and "live in it." They talk openly about why they misquoted a job, why it didn't run well, and whether they can take on similar work in the future or what they'd need to be ready for it, raising the whole shop's level so the mistakes don't recur. Shops that just grit their teeth and promise to remember next time lose that chance to build culture.

Ray says the focus on culture and team building has changed "night and day" since he entered the industry. He acknowledges he may be seeing this through his own customer base, and Chris notes that Paperless Parts customers likely skew proactive. Still, Ray believes culture is becoming table stakes for attracting talent, which ties back to the leadership gap discussion.

What Ray does differently now: written plans

Asked what he does as a leader today that he didn't do two to five years ago, Ray says the company is scaling toward a goal of a $100 million, highly profitable business, so it can reinvest faster in value for customers. The biggest change is that he now asks people for plans. In the early days, the team fought fires all day. Plans were loose and went out the window as soon as they were written. There is still plenty of firefighting, but he now asks his leadership team to step back and write intentional plans for their goals. Not "we're going to sell more," but how.

His metaphor is an orchestra: as it grows, it needs conducting so everyone reads the same sheet at the same tempo, because larger groups are harder to keep in unison. He calls this a completely new challenge for him. He sees himself as the forcing function: "We're following the plan until it's not the plan, and then we're going to write a new plan," but there will always be a written plan. Chris links this to the earlier theme of deciding and pivoting, and Ray says plans are what give a company long-term conviction to weather storms that are likely temporary. That leads back to his claim that experienced CEOs know the right long-term decision. The question is whether they have the conviction to see its benefits, the ROI, come to fruition.

International supply chains and "Cutting Through the Noise"

Asked what they hadn't covered, Ray mentions that Paperless Parts had just launched in Australia and New Zealand, and he raises international supply chains. He argues that everything moves like a pendulum and that globalization swung "a little bit too far," past the point of healthy collaboration into dependence. Chris mentions he is heading to MIT that day to discuss the topic. Ray says the key question is the right level of global collaboration without falling into dependence. He expects the country to "figure that out over the next 12 months" and thinks it could be a good reset toward focusing on what must be done domestically.

Finally, Chris asks about Ray's video series Cutting Through the Noise. Ray says it started by accident: he and a co-founder were "ripping on a topic" during a recorded call, and the company's CMO suggested sharing it on LinkedIn, which drew a strong response. His reasoning for the series is that manufacturers are busy and don't have time to synthesize the flood of content. CMMC is his example of a noisy topic. He wants to cover only the most important thing at a given moment, and "if there's nothing to talk about, we just won't talk."