Sina Chehrazi on culture interviews, mock board meetings, and founder mental health

‍Sina Chehrazi is the CEO of Nayya, a healthcare benefits platform that helps employers and employees save time and money. A child of health practitioners, Sina found an early fascination with care: how others sought it out, regulatory impacts, to his own self-care. After attending Georgetown for business and law school, Sina leaned into his entrepreneurial instincts to start a company that reinvents how benefits are provided and chosen. His leadership style is one that relies on data and when it comes to confronting his own vulnerabilities, he’s humble and authentic. 

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Lessening pain

I grew up in a healthcare family in Northern California. When the holidays roll around, I'm about one of three people who doesn't practice medicine. So throughout my childhood, I frequently hung out at the nurse's station while my dad completed his rounds.

I would spend the day listening to him struggle with sending patients or records from one health facility or clinic to another—and I just thought that was normal. But at some point, I realized it wasn't. What left a lasting impact is knowing just how painful navigating healthcare is.

"It's painful when you're sick. It's painful when you're healthy. It’s painful when you’re trying to pick different plans. It’s painful trying to pay medical bills. No part of the process is easy or pleasant."  

That idea wormed into me. From there, I took a bit of a circuitous route by going to college and law school. During that time, I studied a lot of regulatory and healthcare policy and worked for several startups. My goal became lessening that pain I had seen as a kid. 

In the US, most people get their health coverage through their employer. So we started Nayya, which means renewal or a new approach, with a mission to give people peace and confidence when choosing and using their benefits. In turn, this helps protect household income while helping employers decrease what is one of their largest expenses. 

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How AI will change healthcare 

Even though it’s early days, we can start to see the impact that AI and connected data is making in healthcare, and the potential is massive. I believe it’ll make the complex industry more transparent and drive consumers towards their best action, with the best dollar use, forcing the market to improve itself. And that's really exciting to think about. It’s long overdue.

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The culture interview

We are a little over a hundred people now, so culture is becoming increasingly important. Moxie is one of our core values and you need it in healthcare. If you give up when you get the first no, it will be a challenge to truly drive change in this industry.

Something we’re proud to have as part of our culture is the mix of pace and rigor required for doing great work. Our values are internally well-known and we regularly weave them into conversations such as reoccurring all-hands meetings.

In an effort to help enforce our culture, we also have components of our interview dedicated to it. It's very difficult to level the playing field when it comes to interviewing because some people are better interviewers, and some are worse, but that only has a loose correlation with job performance. The goal of our culture interview is to remove all of that bias. It's not about the right answer. It's really about how you present yourself, what your values are and how those align with Nayya’s. If they don’t, that's fine, but I think both parties would rather find that out at the application stage rather than several months into a job.

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Data and operating cadence

Each month, our COO leads a two-hour meeting dedicated to reviewing operations that looks at every vital sign of the business. This helps us identify where we need to invest more, and where we need to iterate. It’s a great practice for any growing company, but it’s a process that takes a lot of work.

The leadership team goes all the way through the sales funnel, account management, and customer operations to product engagement and recruiting. It’s designed to cover the top metrics for each team. Part of the idea is that we can instantly turn all this preparation into a board meeting and relieve the admin burden on the team. 

Funnily, it’s like what Nayya does for consumers—there is immense value in centralizing data and drawing insights from it.

As a founder, having a great executive team around you is key to successfully running an organization. There's no real perfect job description for a CEO. CEOs come in so many different breeds and types. What matters is knowing where your strengths and weaknesses lie and recruiting execs who fill the gaps in your capabilities. A team that can translate data into action is especially key and can bolster your operations.

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Entrepreneurship is a mindset, not a technical skill

I was part of a teaching fellow program at Georgetown Law, where I talked to aspiring entrepreneurs, brought in guest speakers who were entrepreneurs, or interviewed founders.

One of my main takeaways was this constant deluge of things you deal with as a founder. It never ends, and there are no breaks. Having the mental and emotional capacity to deal with a life like that is rare—maybe it can be taught, maybe not—but what matters as an entrepreneur is understanding how much you can take on. It's not really about the news but how you react to it. It sounds easy, but if it was, everyone would do it. 

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Board dynamics

Because I had the luxury of talking to many entrepreneurs, interviewing them, and reading about them in school, I absorbed a lot on board construction.

Entrepreneurs can get into the trap of thinking that the board will build their business. But the board's there for governance and to recognize patterns. They aren’t there to solve your problems. There’ll be insight or advice, but their main objective is to ensure you don’t get off track. Your job is to win; their job is to coach. 

A great board can elevate a founder far past their native talent. Having a team of seasoned, intelligent investors and operators to help you is great when you can have it. Investors with ex-operating experience who've walked a mile in the shoes of a company leader were key to building my board.

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Founder mental health & personal development

With our partnership with Felicis, they offered to pay for development services for me through their founder’s pledge. Now, every week I go to therapy. If I didn't have the Felicis pledge, there's no way I would've ever started going. The fact that Felics not only completely subsidizes it but also endorses and normalizes it makes a huge difference.

"Striking a balance between being the CEO and my personal leadership evolution is a big focus."

You can call yourself the CEO, but it's like CEO of what? Anybody can put those three letters in their title. It's not really about the letters, it's about what they stand for. When I was younger, I looked at leaders as infallible. The reality is that they’re just the same as everyone else. I’d love to develop the most as a leader over the next few years by asking better questions and being more critical about the long term.

CEOs across organizations are working through a lot of the same challenges. To me, the most important thing is to be genuine. Your role as the CEO is to put a lot of checks and balances around alignment and executive leadership responsibilities. It’s less about fiefdoms and more about giving people a clear sense of ownership. 

The more a company scales, the more you worry about resource allocation and how investment performance is tracked. Questions like: how do you develop short-term mile markers? How do they feed up to long-term goals? And what's the communication around those short-term mile markers? It feels asinine, but it's what makes a company scalable.