Advice / Career Paths / Career Stories

Taking Risks With Your Career Is Scary. This Leader Is Proof It Pays Off.

Bryan Giaimo, the General Manager and Head of Platform at Stride.
Bryan Giaimo, the General Manager and Head of Platform at Stride.
| Courtesy of Bryan Giaimo

Bryan Giaimo has accomplished a lot in his career, from holding leadership positions at some of the biggest names in healthcare to co-founding a management consulting firm. But then came an opportunity to become the General Manager and Head of Platform at Stride, a digital health startup whose technology helps consumers, employers, health plans, and brokers streamline individual benefits enrollment. For many reasons, he knew it would be the perfect next step.

“I was ready to roll up my sleeves and start building from within to make an even larger impact in healthcare,” Giaimo says. “Stride stood out in a big way because of how passionate everyone at the company is about our mission to increase access to health coverage. The more people I talked to, the more excited I became about the role.”

The company’s remote work policy was another selling point; Giaimo, a father of three, now has the flexibility to spend more quality time with his family.

“Everyone at Stride understands the realities of doing important work while also having young kids,” he says. “That was extremely important to me.”

Here, Giaimo talks about why working in the healthcare industry is anything but boring, the greatest benefit of joining a smaller company, and the importance of leaving your comfort zone.

What inspired you to pivot away from consulting?

Consulting was a great place to learn about a broad mix of issues in a short period of time, and I very much enjoyed being able to work for multiple different companies and teams along the way. That said, it was difficult feeling like I was sitting on the sidelines “advising” others. The pivot out of consulting has been truly invigorating from that perspective.

What has been the greatest benefit so far of working for a smaller company in the healthcare industry?

At a smaller company, you are exposed to so many facets of the business that you typically don’t see in a larger organization. I’m not just talking about exposure to senior leadership, which is also true. You get to collaborate in a real way with other teams because everyone is working toward the same goal and coming together to get the job done. This is a massive opportunity to learn about areas that aren’t directly within your purview. More importantly, it helps you see and appreciate how all the different pieces of an organization need to come together in order to serve your customers.

What are you responsible for as the GM and Head of Platform at Stride?

I’m responsible for the strategy, sales, and client success functions that are aimed at growing and maintaining the portion of our business that serves enterprise customers—like health insurance companies and insurance agencies—with our white-labeled software platform. Tactically that means my team sets the strategy for where this line of business needs to go (what markets to serve and with what products); executes the sales and growth activities needed to reach new customers; and ensures that every one of our customers is successful in implementation, engagement, and ongoing support.

Part of what I love about this role is that making it all work well requires a significant amount of cross-functional collaboration with marketing, product, design, engineering, and operations. A big part of what my team does is make sure those areas are working together toward the common goal of growing our reach and serving our platform customers.

As a newer leader at the company, what’s a project or initiative you’ve taken on and what impact has it had on the business?

Early in the year, after getting some useful market feedback in client and sales conversations, we determined that we needed to provide an additional integration option for our enterprise customers. I was able to work with our cross-functional team to quickly build a business case for adding this new functionality, and then I worked with the design, product, and engineering teams to bring it to life. I love the process of seeing something through from market observation to testing to business case development to design and implementation. It turned out to be one of our more requested features so it was well worth the investment.

How do you think your direct reports would describe your leadership style?

With a high-performing team like I have today, I like to give as much trust and autonomy to my direct reports as I can. The reality is in many instances they know their areas of expertise much better than I do; my job is to set the strategy and direction for how to meet our business objectives and make sure I’m doing everything I can to make them successful. That said, I’m always willing and able to pitch in and get into the nitty gritty details when I need to!

What is the biggest challenge you’ve faced in your career and how did you overcome it?

The biggest challenge has been being able to put fears aside and jump headfirst into exciting but scary-looking opportunities. Several years ago, I left a great, stable, high-growth job at a large healthcare organization to help build a management consulting firm from the ground up. That was an incredibly difficult decision to take a big risk. Many people thought I was crazy for doing it (myself included). Similarly, it was another big step outside of my comfort zone to come to a startup digital health company and take on the role that I’m in now.

In both of those instances I was so glad I did. You learn the most when you’re uncomfortable, and you have to be willing to take the leap when you have the opportunity to do so. It’s much easier said than done, and even harder to remind yourself of that when you are facing those decisions in the moment.

What’s a common misconception about working in healthcare and how would you respond to it?

I’ve done a lot of work in the healthcare and insurance space and some people hear that and think it sounds pretty boring. The truth is there is so much interesting and exciting work going on in healthcare, and healthtech specifically. It’s a big, complex system with a lot of room for growth and improvement. And the impact you can have on people’s lives is a constant driving force to keep you motivated to build things even better. That’s a big part of the reason I joined Stride.

What’s your go-to activity to unwind after work these days?

With a 6-year-old and twin 4-year-olds at home, most of my activities have to do with shuttling around to soccer practices and swimming lessons or playing with the kids around the house. Part of the reason I love Stride’s remote culture is that it enables me to do that sort of thing. When I do get some time to unwind, I love my family’s Friday indoor pizza “picnics,” when we all watch a movie together while we eat, as well as our weekend morning walks to the local coffee shop.

What are you currently reading, watching, or listening to?

I just finished House of the Dragon and now I’m finally getting around to watching Ted Lasso, which I’m thoroughly enjoying. As for reading, I recently finished a book called Leadership in Turbulent Times by Doris Kearns Goodwin. It is a mix of history, politics, and leadership lessons, and covers a lot of ground but in a very accessible way—I loved it.

Updated 11/14/2022