Why Learning to Trust Your Gut When Scaling Your C-Suite Is Key

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Back when my co-founder Bob Lindner and I were trying to figure out if we even had a viable business concept, building out an entire leadership team felt far into the future. Early on, when our resources were limited, every hire represented a major decision point.

Would the person we were vetting share our passion for solving complex problems? Did they possess the right skill set to scale the business? Could they lead teams and help them produce results? Would they help us build a culture that prioritizes science and imagination? These and many more questions constantly ran through my mind.

But time flies when you’re building a business, and before we knew it, we had secured seed funding and were making real inroads with health plan customers. We were absolutely obsessed with finding ways to bring down the healthcare industry’s annual $1 trillion in administrative spending — and it became clear that automation and Bob’s unique approach to AI was the way forward. As we grew beyond pilot projects and started bringing on national payers as customers, we soon found ourselves in the position of picking a set of partners to join us on this wild ride of scaling our startup.

Overall, our experience growing the company’s leadership team has been positive, but like every young business, we did make a few mistakes along the way. As an advocate of transparency and shared learnings, I’m eager to put forward the three main lessons learned while scaling our C-suite, in hopes that they help other entrepreneurs.

Tip #1: Be honest with yourself, know your limits and be willing to fill the gaps

I’ve never felt that we had to fit into the Silicon Valley mold of a tech startup. In fact, my co-founder and I both came into healthcare as industry outsiders. And we’ve always charted our own course, and that applies to hiring as much as it does to any other area of the company’s development.

Part of being successful in any leadership position is making an honest assessment of your own areas of expertise and then working hard to find superstars who can fill in the gaps. This goes beyond assessing skills like the ability to build a financial model or test automation. It requires deep reflection on your ability to coach, persuade and make balanced judgments under pressure. Find early partners that complement your skills, augment your strengths and fill gaps where you struggle.

Speaking of investors, on top of evaluating our gaps and seeking candidates to fill them, we had to answer to the people funding our passion project — who, quite reasonably, wanted some say in our initial executive hires.

Even taking these considerations into account, we still had a lot of freedom in terms of who we hired. When we met amazing people, even if they didn’t fit the exact position we had set out to hire for or look like a traditional candidate for an executive role on paper, nine times out of 10, we brought them on board.

Our chief people officer, for example, is an entrepreneur first and early in her career founded a hospitality chain. She discovered her love for growing and nurturing talent later in her career. She had talents and experience to bring that went beyond the traditional HR model — we believed it would be an asset, and we were right. So much of what we do in startups is based on instinct.

Tip #2: Every single early employee (including C-suites) needs to be scrappy

Being a C-suite at a startup almost isn’t worth a comparison to roles with similar titles at large, well-established companies. Every single person, from the bottom to the top, has to roll up their sleeves and be willing to take on tasks as large as building a first-of-its-kind technology and as small as restocking the toilet paper in the one working bathroom in the business’s first, corporate headquarters. Even today, with a workforce of 100 spread across the United States, we need our employees to be scrappy. And while many days I have the pleasure of strategizing about the business’s future, there are just as many when I personally am engaging in the trenches with the team to ensure our customers get the best from us. Our startup is our baby, and as the saying goes, it takes a village. In this case, a scrappy, smart and patient village.

For our team, that means everyone, including me, learns the job of our customer success team. We experience the product in a hands-on way and build empathy with our customers. In a crunch, anyone can jump in and meaningfully help a customer through a task.

Tip #3: Don’t assume that candidates that come from larger, successful brands will be a fit for your early-stage venture

My final tip speaks to an error that I’ve found is common among startup founders — hiring an experienced executive from a large, successful brand because you believe that person will bring whatever magic they made at X, Y, or Z household name to your business.

Executing on a well-structured plan and building strategy and procedures from scratch require wildly different skill sets. Some of our most talented leaders have built small companies and helped to grow them through acquisition or exit.

Remember, even at the growth stage, you are searching for architects and builders in every role. Our CFO came to us from a fitness tech startup. Not exactly what one might look for on a resume for an AI company leader, yet his background in managing cash and creating dynamic models to adapt to changing markets is serving us particularly well at this moment.

It’s worth repeating — trust your gut!

If you leave this piece remembering one thing, and one thing only, I hope it’s to trust your gut. Your startup is unique because of you. If it succeeds, it will be because you didn’t let others overly influence key decisions in the journey to company maturity.

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