Jason Ray had fifty parts to find quotes for. His co-founder, Jay Jacobs, sent him out to see how the market worked. Ray approached forty shops. Two responded. Somewhere between a drawing and a finished component, American manufacturing had developed a persistent talent for leaving a customer waiting.
The experiment gave a small, countable shape to a problem Ray already knew from military logistics. Before anyone could cut metal, someone had to work out a price and agree to the job. Even a capable factory could be difficult to buy from. The machinery might be ready; the conversation was stuck.
That gap became the business of Paperless Parts, the Boston software company Ray co-founded in 2017 and leads as CEO. His route there involved an economics degree, a recession, naval service, and an unsuccessful effort to buy a machine shop. It is a career assembled from plans that became more interesting when they failed to cooperate.
One early sourcing exercise, as recalled by Ray. Each square represents one shop; yellow marks the two responses.
Wall Street had other plans
At Trinity College, Ray studied economics and history and wrestled. He graduated in 2008, a year with a particularly unhelpful attitude toward young people expecting to enter finance. Wall Street had seemed a plausible destination. The economic downturn required a different calculation, and Ray applied to naval officer candidate training.
His education had depended on financial aid. Before graduation, an internship at financial public relations firm Finsbury gave him another sort of assistance: alumni willing to take a student seriously. Andy Merrill and Tripp Kyle taught him about working in business. Years later, when Ray had jobs to offer, he would revisit that experience from the other side of the desk.
There is an appealing economy to this part of his story. An introduction becomes an internship; an internship becomes a memory of being helped; that memory eventually becomes a hiring practice. The return on an afternoon spent with a student can be difficult to enter in a spreadsheet.
A supply officer meets the supply chain
In the Navy, Ray served as a supply and logistics officer and worked on advanced manufacturing initiatives, including additive manufacturing. The work put him close to the distance between what an organization needed and what its purchasing processes could deliver.
He has recalled the difficulty of buying parts from American machine shops while serving aboard a minesweeper in the Persian Gulf. Later work at the Pentagon deepened his involvement with manufacturing. The attraction was practical: physical equipment depends on physical components, and a supply problem can survive a remarkable amount of paperwork.
Ray also earned an MBA at Babson College. His subsequent work included manufacturing consulting focused on process improvement and automation. Across those experiences, he kept returning to the friction around obtaining custom parts. A drawing could describe something precisely while the commercial process around it remained slow and fragmented. Manufacturing software offered a place to work on that mismatch.
The shop he never bought
Ray initially wanted to own a machine shop. Jacobs, who had built the sheet metal prototyping business RAPID, advised his search fund. After about a year looking, no acquisition followed. Ray worried about businesses whose essential knowledge resided in the departing owner’s head.
In 2016, Jacobs encouraged him to summarize the problems he had observed. The summary looked like a software business. Ray pointed out his lack of software experience. Jacobs replied: “You’ll figure it out.” He suggested Boston and the name Paperless Parts.
Ray had gone looking for a business to acquire. He emerged with a business to build and a subject he would have to learn.
“You’ll figure it out.”
Jay Jacobs’s advice to Ray, as Ray later recalled it
The customers found another use for it
Paperless Parts began with a marketplace approach, an attempt to make finding manufacturers easier. The model encountered a stubborn detail: custom manufacturing prices move with materials, timing, capacity, and the specifics of a job. A price on a marketplace could differ from the price a buyer obtained directly. Confidence suffered.
Meanwhile, participating manufacturers found something useful inside the system. They could upload parts, use its pricing capabilities, and produce quotes for their own customers. The people supplying the marketplace were showing the company a different business.
Paperless Parts shifted toward selling software to manufacturers. Ray’s team could help a shop handle its existing relationships more efficiently, with tools suited to estimating and quoting. It was a revealing adjustment. Customers had provided feedback by putting the product to work. The founders’ task was to notice which work mattered.
- 01 / A designA customer has a part to make.
- 02 / A quoteThe shop evaluates the job and sets a price.
- 03 / ProductionAn accepted job moves toward a physical part.
An editorial schematic of the workflow. The highlighted step is Paperless Parts’ focus.
The information has to survive the handoff
Ray’s writing about job costing shows how closely he pays attention to the routine beneath a software promise. Costs depend on accurate records. If employees fail to enter information consistently or allocate their time correctly, the resulting numbers lose their usefulness. Buying a system does not automatically fix the habits that feed it.
He has described machine monitoring as a way to obtain production information directly, reducing dependence on manual recording. The next question is how to bring that knowledge back into the next quote. Work completed yesterday should help a shop understand work it might accept tomorrow.
That attention to the handoff helps explain his choice of business. A quote joins technical understanding to a commercial commitment. It asks a manufacturer to translate what it knows about making something into a promise a customer can act on. Ray chose to build around that translation, with all its ordinary, expensive opportunities for misunderstanding.
Hiring, with a return address
As the company grew, Ray drew on Trinity’s alumni network. Dana Wensberg, a physics and engineering student, joined as an intern and later became a computational geometry software engineer. Other students followed. By the summer of 2019, four Trinity class years were represented in the business.
The connection had a mechanism beyond school affection. Former interns went back to campus and helped identify the next group. Ben Barton heard about Paperless Parts through Wensberg’s enthusiasm after an internship. A good experience became a credible recruitment message because someone who had done the work was delivering it.
Ray’s later comments on hiring emphasized the expense of coordination. In a 2022 discussion of the software talent market, he argued for paying more for capable people and keeping teams smaller. Adding employees increases the number of conversations required to get something done. His rowing analogy is apt for a former naval officer: one person can steer alone; a hundred need considerably more organization.
A management problem has managers in it
Ray brings a similarly direct argument to manufacturing’s talent debate. In his public conversations, the familiar skills gap becomes a question about management. How are employers investing, organizing work, and making their businesses places where capable people want to stay?
It is an argument with some bite because it gives the people in charge something to do. An investment mindset, in his account, changes both the business and the kind of team it can attract. His software work and his leadership advice share an interest in the choices surrounding skilled labor: what gets attention, what gets funded, and what consumes time.
In 2021, Paperless Parts announced a $30 million Series B led by OpenView. The planned uses included further estimating automation and tools for interpreting technical drawings. The funding put resources behind a specific proposition: job shops deserved software built around their particular work.
Series B announced in September 2021, led by OpenView. Company financing, not Ray’s personal wealth.
The business subsequently appeared at number 96 in Deloitte’s 2023 Technology Fast 500, with reported revenue growth of 1,527% over the ranking’s measurement period. Those are company results. They give a sense of how far the quoting problem had carried Ray’s original investigation.
Still asking what holds up the work
By 2026, Ray was also hosting Cutting Through the Noise, a series of conversations about the decisions facing custom manufacturers. An August episode with Athena Manufacturing’s Matt Newman examined disciplined growth. A conversation with All Metals Fabricating’s Lance Thrailkill explored getting employees involved before buying new technology.
The subjects extend beyond software features. Faster equipment can move a constraint elsewhere. A purchase can look sensible on paper and still fail to become useful in practice. Ray’s interviews give shop leaders room to discuss those complications, with the people making the decisions doing the talking.
He also continued appearing in industry discussions, including a September 2026 IMTS panel on when to turn work down. That is a telling subject for someone whose early experiment produced so few replies. A manufacturer needs a way to evaluate an opportunity, decide whether it fits, and communicate the answer.
Ray also speaks plainly about effort and resilience. His account of success puts weight on working hard and continuing after setbacks. Those convictions sit comfortably beside the less glamorous episodes in his career: a changed plan after graduation, an acquisition that never closed, and a product whose customers helped redirect it.
Ray’s ambition has remained attached to making manufacturing easier to do business with. The machinery is an essential part of that story. So are the estimate, the introduction, the experienced employee, and the customer waiting for a response. His career has followed those less theatrical dependencies with considerable persistence. Before a part takes shape, somebody has to answer.