Innovation Blog

An Entrepreneur Shares Insights On Switch From Assessing Startups for 12 Years to Joining a Startup


I spent 12 years at Willis Towers Watson (WTW) consulting with employers’ HR, Benefits and Wellness teams. I led the Health Imagination team, assessing 100s of health care startups every year, helping bridge the gap between early stage companies and large employers who are trying to manage the health and wellbeing of their employees. It was truly an amazing role to sit at the intersection of the market meeting entrepreneurs and listening to employer pain points and feedback.

Eight months ago, I joined my favorite healthcare startup, Buoy Health. I had first met our CEO, Andrew Le, four years ago when he was pitching us at WTW. It was early days for Buoy at the time, but I was truly impressed with Andrew and always kept in touch.

After meeting up with Andrew last summer, I joined the Buoy team to help build the employer market. It’s been an incredible experience and the challenges, perks and emotions from this side of the table are quite different from the assessment side.

Lessons Learned From Assessing Startups

Challenges – when you see hundreds of companies every year, each entrepreneur has something unique about their story, their business, and the problem they are trying to solve. The challenge, as we used to say, was “innovating with purpose.” You might discover an amazing technology in a device or a cool breakthrough using genomics, but what’s the “so what?” Our key questions were always: Will it help lower costs, will it improve health, will people want to engage with it and will this provide a better employee experience? It was a challenge to keep up with all the changes.

Perks – you see EVERYTHING. There is a huge difference between companies just starting out and building a minimum viable product (MVP) vs. the companies who have had actual customers, employees are engaging with the service and results are measurable. That being said, I always took something away from every pitch. Even if it was not ready for prime time, the way someone approached a problem, the technology they were using, or the way they crafted their story was invaluable. I loved meeting new entrepreneurs and helping in any way I could.

Emotions – when you are in the middle, you share the emotions with both the startup and the employers who begin to implement the new solutions. On the startup side, you can see people get so excited to attend innovation days and get exposed to employers who may benefit from their solution. On the employer side, you share the skepticism at first, but then you too get excited because you have seen a consistent paint point – diabetes, maternity, overutilization of services, etc. – and finally have found a new approach!

The Ins and Outs of Joining A Startup

Challenges – Things can change daily so there are a lot of challenges, but it’s all in how you handle them. There is urgency. You need to get your message out, but you also need to control your messaging. Hiring is SO crucial. Focus is a must, but also incredibly difficult. Everything I used to hear when talking with entrepreneurs – all the clichés – are spot on. You definitely need to wear more hats every day, but that just means you learn a lot of new things!

Perks – It’s rewarding and impactful. Despite a small team, we all have such unique skillsets and can quickly contribute to tangible improvements in our business. We can move from consumer research to product design to development to in the hands of our users at a pace like nothing I’ve seen before. And even though the pace is fast, the attention to detail and thoughtfulness behind the scenes in each step is remarkable. When you are early stage, celebrating successes is a blast!

Emotions – Rollercoaster! It’s so important to have a team and a culture you can trust. I’m grateful that at Buoy we all know we have each other’s backs. In startup world, you know there will be times of stress and various highs and lows, but having an amazing team to celebrate the highs and to support (and fix) the lows, it makes everything worth it.

Reflection and Next Steps

We’re all in this together. Whether you are assessing, investing or building a health care startup, we all are trying to improve outcomes and make the healthcare system better. It’s the collective ecosystem that pushes us all in the right direction.

My inbox used to be full of entrepreneurs reaching out to pitch our team. Now my sent box is full gathering feedback from employers, health plans and consultants. Your network and their expertise is so incredibly valuable. I’ve been fortunate to tap into a lot of brains since making the transition!


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