Will Young

Will Young is the co-founder and CEO of Sana, a health care company that provides Fortune 500-level health care to small businesses at affordable prices. Will has a passion for fixing the broken healthcare industry, and made his first charge at that when saw an underserved and often overlooked market in small businesses and their employees. Since 2018, Sana has grown to thousands of lives covered and over 100 employees. Prior to Sana, Will helped hundreds of small business owners manage payroll and benefits as the head of operations at Justworks, a venture-backed PEO. Will also spent two years at Google before earning his MBA from Harvard.

Where did the idea for Sana come from?

Before Sana, my co-founder Nathan and I were working at another startup called Justworks. We sold health insurance to hundreds of small businesses. Legacy health insurance carriers offered a product that was expensive and difficult for our customers to use. There was a clear opportunity to build a better health plan for small businesses. We built Sana around the needs of these customers and on modern technology.

What does your typical day look like and how do you make it productive?

I wake up and get my one year old daughter ready for the day with my wife, which is a wonderful way to start each day. Once work starts, I try to keep my calendar free for the first hour or two of the day and I use that time to explicitly write out my priorities. I make sure to keep the ball moving forward every day on a handful of strategic initiatives. It’s important to do that before I look at my calendar or email. At a fast growing startup it’s easy to slip into being reactive – there are just so many demands on your attention. You really need to carve out time for the proactive stuff. The rest of my day is spent doing meetings, emails, & calls.

How do you bring ideas to life?

In the early days Nathan & I would have ideas and then just build them ourselves. Now, we have so many talented people at Sana, it’s more of a filtering, consensus-building, and resource allocation process. I spend time with our execs debating and committing to a direction we want to go together, then we assign directly responsible individuals and financial resources to the highest priority initiatives.

What’s one trend that excites you?

There has been a surge in venture capital investment in digital health companies in the last couple years for treatments across the care spectrum (mental health, fertility & maternity, musculoskeletal, telemedicine, etc). Sana partners with a lot of these innovative startups and offers them to our clients. So as all of those solutions get better and better, our product gets better and better. It’s an exciting time to be a healthcare entrepreneur and to build Sana specifically.

What is one habit of yours that makes you more productive as an entrepreneur?

I spend a lot of time with my family, with Slack and email turned off. Building a company is a rollercoaster. Staying balanced and being in the right frame of mind when things are stressful matters more ultimately than working a few additional hours.

What advice would you give your younger self?

Take more risks, sooner. People (myself included) are generally too risk averse. Most people are worried about trying something and failing – whether a new job or starting a startup. The short term costs are obvious and painful (less guaranteed income, losing face in your social group), so people avoid taking risks, even though the long-term benefits of taking risks (personal growth, more ownership) are tremendous. Just from a personal growth standpoint, taking a lot of risk and being outside of your comfort zone is essential.

There is also tremendous asymmetry in returns in life and in startups (VCs talk a lot about power laws and it’s one of the amazing truths hiding in plain sight). A very small number of organizations drive the majority of returns and impact on the world, and if you want to maximize your impact you should try to be a part of one of them. The impact your career or business or non-profit makes on the world is actually the result of a portfolio of bets, and you’re generally better off making more, riskier bets than fewer, safer bets to maximize your chances of being associated with one of the outliers that drive most of the impact.

Tell us something that’s true that almost nobody agrees with you on.

Nathan & I founded Sana remotely (he was in Columbus, I was in SF) and hired all of our early employees remotely. At the time (pre-COVID), pretty much every investor (even the “contrarian” ones) told us that was a recipe for failure. Four years and 100 employees later we are still going strong with the fully remote model.

Obviously COVID changed a lot of people’s perspectives on this, but we were definitely outliers in the beginning.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Skip levels & customer interviews. One risk you have as founder or CEO once the company gets beyond a few dozen employees is losing touch with customers and employees who don’t report to you. You need to create a regular cadence to listen to customers & more junior employees so you actually understand what’s driving the business day to day.

What is one strategy that has helped you grow your business?

Automated NPS surveys of our customers. The best “growth hack” is happy customers because they become referrers and references. Staying laser focused on customer happiness and retention from the beginning is essential.

What is one failure you had as an entrepreneur, and how did you overcome it?

It took us a year and a half to get our first customer. That wasn’t just one failure – it was dozens of failures back to back to back to back to back – and it was excruciating. We eventually found product market fit through force of will. More specifically, by listening to prospective customers and iterating on the offering until we got to our first “yes”.

What is one business idea that you’re willing to give away to our readers?

This is in the weeds, healthcare specific, but I’ve always thought someone should create an “Open PPO” network. Doctors offices have all these redundant contracts with insurance companies and insurance companies have redundant provider contracting departments. So much wasteful redundant overhead. Someone should create a platform / marketplace with essentially contracting middleware and save everyone a lot of money.

What is the best $100 you recently spent? What and why?

I bought my wife a weighted blanket for her birthday. She loves it.

What is one piece of software or a web service that helps you be productive?

I started using Roam Research to take notes. It’s how I organize my thoughts at the start of the day and helps me keep track of priorities.

What is the one book that you recommend our community should read and why?

The 5 Dysfunctions of a Team is a great read for fast-growing startups. There are common patterns for how scaling breaks interpersonal relationships at the executive level and you need to navigate those if you want to be successful.

What is your favorite quote?

“The future is already here – it’s just not evenly distributed” – William Gibson

Key Learnings:

• Don’t allow scaling to put distance between you and your customers or your frontline team members. Stay in touch with them on a regular cadence to make sure you keep a 360 degree view of the business.
• Setting aside time to be proactive is key. Executives can spend their entire day reacting to the demands of others unless they’re intentional about setting time to proactively tackle the most important work.
• Being in balance and well-focused may be a bigger accelerant to productivity than a couple of extra hours “in the office.” Do what you need to do to stay balanced.
• Finding product-market fit is hard work, but worth it. You’re unlikely to nail it day 1; listen to why prospects aren’t buying, and iterate your way there.