As Chief Legal Officer at Pearl Health, Jon Goldin helps the company navigate the complex regulatory, contractual, and ethical landscape of value-based care — all while ensuring legal doesn’t slow innovation down. In this conversation, Jon reflects on his path to Pearl, the evolving role of in-house counsel in startups, and why the best legal teams are partners, not roadblocks.
What do you do at Pearl?
I’m the Chief Legal Officer, which means I help Pearl mitigate risks and comply with legal requirements. We’re in an extremely regulated space — Medicare, HIPAA, state laws — and we operate a contract-heavy business, so I work closely with our sales team, product team, and others to make sure we’re protecting the company while moving quickly.
What drew you to Pearl in the first place?
I’ve known Mike Kopko for over a decade — we met at a fundraiser for a mutual friend who was running for office — and we stayed in touch over the years. What really excited me about Pearl was the alignment between the public interest and the company’s profit motive. We make money by doing good, and if we don’t do good, we don’t make money. That’s rare and really motivating.
You joined Pearl as the first legal hire. How do you approach the role differently than a typical lawyer might?
My goal is not to be the person who just says no. I try to get involved early in projects, to understand what the team is trying to achieve. That way I can row in concert with them — contribute, refine, and make the idea better — not slow it down. We’re building the plane while we’re flying it, and Legal has to help make that possible.
Your work touches so many parts of the organization. How do you think about building trust and being a collaborative partner across teams?
One of the things that helps establish credibility and trust is simply logging time with people. It’s about making sure that when someone asks Legal for assistance, it doesn’t feel like they’re throwing a document into a black hole. You want people to know it’s not going to disrupt the schedule or slow down the forward motion of their work.
That applies whether we’re talking about product development, engineering adding sophisticated AI features, our growth team looking at new deals, or marketing crafting materials to promote Pearl’s message. Time spent listening and collaborating is essential.
Have you had opportunities to work with teams in more of a co-pilot role — especially during something like a sales process?
Yes, I’ve had the chance to partner closely with our growth team during the sales process, especially when we’re working with counterparties who might not be familiar with the Medicare programs we operate in. Those conversations often focus on how we can structure arrangements in a compliant way that also aligns with their goals.
It’s often more of a collaborative process than an adversarial one. When we can be proactive — discussing the options, clarifying the risks, and helping people understand what’s possible — it builds trust from the outset and sets everyone up for success.
What’s been most exciting about Pearl’s evolution so far?
The slope of our growth has been amazing. We went from 4,000 Medicare beneficiaries to over 150,000 in just a few years. As we collect more data and demonstrate the efficacy of our product, that growth will continue — especially as we expand into new technologies and other areas of healthcare like Medicare Advantage and commercial. We’re building something that could have a profound impact on the sustainability of the US healthcare system.
How do you describe value-based care to someone new to the concept?
It’s a system that changes the financial incentives in medicine. Instead of being paid for every procedure or visit, providers are rewarded for keeping patients healthy. It requires thinking more holistically — helping people between visits, not just during them. And that’s only possible if we give providers better data and tools to act on it.
What’s something you’ve learned from the team at Pearl?
There’s a deep sense of collaboration and kindness here. People have different superpowers — whether it’s sales, engineering, design — and we come together in a way that makes the whole greater than the sum of its parts. For those of the right generation, it’s like Voltron — when the different robots come together, they become a super robot. That’s core to Pearl and how we’re able to accomplish great things. The folks here are not only mission-driven and collaborative, but also kind. That combination is rare — and it makes a big difference when you’re tackling hard problems shoulder to shoulder.
Some have suggested Pearl has a bit of a nerdy culture — would you agree?
These are incredibly complicated subjects, and whether we’re talking about Medicare programs or individual team strengths, we sure can sound a little nerdy. But one of the great things is that everybody seems to groove off of the passion of their colleagues. When folks present to others on their area of expertise, there’s an energy that’s generated that other people feed off of — which is fantastic.
Is that energy and exchange something you see play out in moments like the weekly Team Summits?
Absolutely. I think our team summits are great opportunities to see, appreciate, and learn from the superpowers of our colleagues. Sometimes that means understanding how a new product feature works, or hearing about patient interactions from the customer success team, or seeing new marketing and design materials. Whatever it is, we get to witness the genius of our colleagues — and we genuinely enjoy learning from one another.
Back to your earlier question about being a little nerdy: I think we all enjoy the educational element of it. We’re cheerleaders for each other. We love to see our colleagues succeed because it’s good for the company, it’s good for the healthcare system — it’s a rising tide that lifts all boats.
I’ve heard people say that Pearl is full of folks who love to teach, but also love to be taught.
I agree. I’ve learned a tremendous amount just by listening to colleagues present on their areas of expertise. Whether it’s our growth team, our engineers working on AI, or our finance and marketing partners — I think everyone here enjoys both working in their area of strength and having the opportunity to learn more broadly.
If Pearl gave out superlatives, what might yours be?
At the risk of sounding immodest, maybe “most protective of the company.” I try to think about risks, mitigate them, and help Pearl move forward — without hampering our momentum or creativity.
As Pearl continues to grow, Jon’s work serves as both a safeguard and a catalyst — helping the company move fast without losing sight of what matters. By embedding himself early in cross-functional work, translating complexity into clarity, and building trust through collaboration, he’s helping ensure Pearl’s mission is not only legally sound, but sustainably built.
Interested in joining the Pearl team? We’re currently hiring across various departments and roles. Check out opportunities on our Careers Page.
