joshcooper.net

About — Josh Cooper

01Professional

Chief Product & Technology Officer
PayGround

Since 2025 · Phoenix, AZ

PayGround started on the patient side: one place to see and pay everything you owe across a health system's hospitals, clinics, and labs, instead of six statements and six portals. Then we looked at the provider side and found it in no better shape, so the company now works both ends — providers collect more, more often, and faster; patients get something they'd willingly come back to. I own product, design, and engineering. I came in as SVP of Product in August 2025, took over product that November, and picked up technology in July 2026. We're just under fifty people, Phoenix-based and mostly remote, pushing toward a Series B.

The work is mostly structural. Two sides of a market, one platform, and health systems with a dozen billing entities behind a single patient — so most of my time goes to the architecture underneath that and to running product and engineering as one organization instead of two that negotiate. The bar we hold ourselves to is the barber you wait for: you'll sit there while other chairs are empty, because you trust the work and you can tell he cares about it.

Director of Product Management, Interoperability
Relatient

2024 to 2025 · Atlanta, GA

Relatient sells patient scheduling and engagement software to health systems and large practice groups. I owned interoperability — the integrations to scheduling, billing, intake, and reminders that make any of it work — and the case for what got built. A ninety-day change to how the teams planned cut sprint churn by forty percent and doubled release velocity, and I spent a good share of my time working with Finance and Ops on how the product was packaged and priced.

Director of Product Management
Rectangle Health

2021 to 2024 · Valhalla, NY

A practice management and payments platform used by roughly fifty thousand providers. I started as a technical PM building the company's first integration strategy and its technology partner program, then ran a team of twelve through the largest development effort the company had taken on: three separate products merged into one. ARR rose sixty-nine percent over that stretch and NPS fifty-five.

Systems Analyst to Product Manager, Integrations
Allscripts Healthcare, onsite at Springhill Medical Center

2013 to 2021 · Mobile, AL

Eight years, four titles, one paycheck. Allscripts signed it, but for the first seven I was a Springhill employee in every way that counted — same building, same badge line, same people, same problems. Springhill was Allscripts' flagship Sunrise site and ran every module top to bottom, financials to supply chain, so the work was as deep as hospital IT gets and I was close enough to the floor to see what the software was doing to the people using it.

The shift came when I took over product and integrations. I owned the roadmap — five thousand interfaces used by thirteen hundred staff, with a team of four analysts — and the long job of replacing flat files and overnight SFTP drops with HL7 and APIs. Cloverleaf, Mirth, Corepoint. Plumbing nobody notices until it stops. That's also when I started spending more time in the Allscripts office than the hospital, and eventually consulting across the eastern seaboard, which is where I learned Springhill's problems were everyone's problems.

02Personal

I grew up moving. My father served in both the Army and the Navy, and we relocated every one to three years — which meant an introverted kid who would rather have been playing video games had to get good at walking into a room where he knew nobody. I played baseball and football badly enough to make friends across a lot of different groups. That turned out to be the most useful thing I learned before college.

College itself I mostly wasted. I started in History, switched to Sociology because of one extraordinary professor, and loved it — the study of patterns and behavior at scale rather than one person at a time. I've come to think it's the most relevant degree I could have brought into this job. But I didn't want to be there for the rest of it, and I did just enough to finish. Just before I started, my father was diagnosed with lung and neck cancer and given six months. He lived another twenty. He never ate solid food again after 2009. We spent those years in and out of hospitals and specialists' offices, and I spent them waiting tables and then bartending — restless, reading rooms for a living.

There was a small technical college on my drive to work. I passed it something like a thousand times before I finally stopped, at twenty-five, and looked at the course list: an associate's in computer networking and administration, almost all of it the actual thing and very little of it the wrapper. I signed up for night classes and rearranged my shifts around them. Near the end of the program a vendor came recruiting unpaid desktop support interns for a local hospital — Springhill Medical Center in Mobile, where a lot of my family had been treated. I could get paid to do my hobby, and I could do it for the people who took care of the people I loved. I started in early 2012, fixing printers, removing viruses, and rebuilding PCs, and I was hooked immediately. I did it for free for a year, on top of the restaurant and the night classes. Then one of the paid technicians got caught smoking pot in his car on his lunch break, and in 2013 I got his job. I quit waiting tables and never went back.

What I'm curious about right now is mostly one question wearing two hats. At home, I'm working out the transition from the Josh I've always been to something more like a patriarch. I provide well, the way my father did — but every generation wants to correct something it felt was missing in its own, and I'd like to understand what I'm correcting before my kids have to explain it to me. At work it's the same shape. I spent a long time as an individual contributor who overachieved on the strength of a chip on my shoulder, and a chip doesn't transfer. Working out how to hand a team the results without handing them the grievance is the most interesting problem I have.

Outside of that: I think augmented reality is the next platform — not VR. Something closer to a JARVIS you talk to, arriving first through phones, then through sunglasses that actually look like sunglasses, then through something about the size of an earbud. I don't think the version that ends up under the skin is as far away as it sounds. Ask me in ten years.

03Education

A.S. Computer Networking & Technology, Remington College, 2013. B.A. Sociology, University of South Alabama, 2009.