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Scott Shreeve, MD

Hey there!

I'm the CEO of Crossover Health, a patient-centered, membership-based medical group that is redesigning the practice, delivery, and experience of health care. We offer urgent, primary, and online care to our members who can access our technology platform, practice model, and provider network from anywhere and anytime to optimize their health. Email Me



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David Sunderland recently joined Crossover as Vice President of Finance, after a multifaceted career with companies in varied industries and through an eventful IPO process. The world of finance, and now Crossover, are fortunate that he decided against a career in pro football, and instead, chose to bring a professional intensity along with his love of competition to his career as a finance leader. 

Would love to learn the backstory of where you grew up, how you were educated, and what you worked on before joining Crossover?

I was born and brought up in Maryland, and went to Lehigh University in Pennsylvania, which is where I studied finance and met my wife (she played lacrosse and I was on the football team). I had been a three-sport athlete in high school, but my size and frame led me to play the gridiron where I enjoyed quite a bit of success. After my college career wrapped up, I tried out for the Baltimore Ravens; competing at that level was an amazing personal experience for me. Unfortunately, I didn’t make the cut and it was only after that dream had come to an end that I started to take stock of the toll the sport had already had on my body. I came to peace with the outcome and was ready to move on.

I started my finance career at Black & Decker, and then moved to international finance management at a division of the Thomson Corporation called Thomson Prometric, based in Baltimore. Prometric was a pioneer in computer-based testing and assessment. I spent almost five years there, and got a lot of valuable experience early on in my career. I worked for some great leaders and mentors and was given the opportunity to spend two years working in Australia as the finance lead at Thomson’s Asia Pacific office. I was based in Sydney, but spent a lot of time in Singapore and China, as well as in the company’s office in Kuala Lumpur. It was a phenomenal opportunity at a young age to learn about different cultures and understand what a regional view looked like versus a corporate view. 

Once that assignment was complete, I moved back to Baltimore and realized I needed a change of scenery and a change of pace. I landed a position with Gateway in San Diego, and later transitioned to Senior Manager of Financial Analysis at the Orange County offices of HSBC, a global bank. My boss at the time pushed me to attend the MBA program at UC Irvine. She knew I’d be on the younger side but thought I had a lot of potential and would be a great fit. It was a tremendous program, and exposed me to a lot of great people. It ended up being a catalyst to look for something new after almost four years at the bank. I decided to make a move to Oakley, the sunglass company, and again, had an awesome time, working with the sales and product teams,  manufacturing, supply chain, and business analytics. My role was to support the business with finance insights, reporting, and I ultimately became a strategic partner. Oakley had such a powerful culture—and I saw how it really shaped the business. It was a great experience and I learned so much from my colleagues and leaders. 

I next had an opportunity to join Emerald Expositions, a company that runs B-to-B tradeshows and events for companies. It was my first experience as part of a private, equity-backed firm, and I like to say that I got 20 years of experience in the six years I was there, first as a VP and then later as the Senior Vice President of Finance. 

The plan was to carve Emerald out of the PE firm that had acquired it, so I had to create a standalone finance infrastructure—including all the parts that set it up like the planning process, how we would budget and forecast, and putting in the right systems that would allow us to scale and grow. I had to develop the planning process from scratch and hire and lead the team. The process eventually led to an IPO. In my time there, we went through all the ups and downs a business can experience—we closed 19 acquisitions, went through management changes, learned how to deal with pre-public and post-public stress, and worked through several major pivots to the strategy. It was an awesome journey working with investors, going through the process to become a public company, and then experiencing life on the main stage of Wall Street.

Seeing the impact of not hitting your numbers out of the gate—when you have to change guidance, field the questions you get from investors, and recraft the story—was a lot to go through with the leadership team, specifically the CFO and the CEO. The events ultimately led to a lot of management changes and it was eye-opening to be right in the center of all that storm. It really shaped the way I talk about the “narrative beyond the numbers” and I got to see directly the impact that can have on the price action of the stock as well. 

You have a remarkably broad range of experience. How has that influenced how you set up systems and manage within a business? 

That’s a great question. I never wanted to be tied into one industry. In my field, whether it’s industry A, B, C, or D, you’re always looking at the same set of challenges: How should we look at data? How should we invest in systems and platforms to get data out to our leadership team? How do we interpret that information? 

My approach has always been to get really good at knowing how to address these challenges, and then applying it across any industry. It doesn’t matter if it’s banking, healthcare services, or consumer products, you’re still trying to solve the same problems. Of course you have different metrics, different variables, and different data points, but you can still apply best practices. You can use all of it to learn and grow from your experience, not just from your current company but also (because I’m so industry agnostic) from what you did in the past and in different sectors. 

I suspect that finance is probably more amenable to that attitude than almost any other part of a company.

Yeah, you’re exactly right. Once you master the basic skills, and the basic architecture of how a company runs, you will find that regardless of the industry, most companies have to be run financially in a similar way—things like reporting, forecasting, budgeting, etc. are pretty consistent. I also found that it makes for an interesting career to get really good at solving the issues in one industry and then seeing how that experience might be applied to other industries. Also, in terms of finance people, most will decide to try a vertical route in their career—sticking primarily within a single industry. I’ve conscientiously tried to be deliberate about going horizontal across industries to broaden my learning and experience. I think it has really paid off for me personally. 

How has all of this experience affected the way you look at specific finance challenges?

Really hard challenges also create great opportunities to learn and grow. I’m really big on mentorship, leadership, and helping people see experience through a learning lens. The day you stop learning is the day you stunt your growth. I have had this brought home to me over my career in so many different ways—which has really given me a growth mindset within my discipline. I am always open to systems, process, and new ways to do things better at scale because I think the broad view I have gained over my career has allowed me to have a strong experience base to draw from. 

How did you end up coming to Crossover? 

In early 2020, the CFO of Emerald was let go and the board brought in a new CFO, along with a lot of other management changes. This was right before COVID hit and around the time my father passed away from cancer, which was a very challenging time for me personally. I started to consider switching industries because I could see the long-term effects that COVID was going to have on the health of the events space industry. I mean, we are reliant on conferences to generate revenue and we couldn’t see many scenarios when that was going to come back anytime soon. So it was really a combination of factors that led me to the feeling of just needing a fresh start. I wanted to take all that I had accomplished and learned over the last six years—both personally and professionally—and share it with another company where I could help create value. 

I started to talk to people in my network, people I regard as mentors, about what my next step should be. I also worked with a recruiter I’ve known and used for years. I wasn’t even aware of Crossover but went through the interview process and liked the story. I have a lot of respect for people like Nate and Scott that have that entrepreneurial spirit where they can start something from nothing and create a really powerful environment for people. I admire the fortitude that it takes to do that, and hearing their story and journey made me think; even though I’m not a “healthcare guy” and I’ve never worked in this industry, maybe there are things I can do that will bring value to the company. My mentors said just jump in with both feet, you’ll do great. The way I was raised taught me that when great opportunities like this come along you should be thankful, humbled, and then be prepared to absolutely crush the opportunity. I have always been willing to bet on myself and this opportunity was another gift to open and trust in myself to be able to deliver. I will take those odds all day long!

Part 2 of our interview with David will speak about his new role at Crossover, the correct framework to consider the role of finance, and how the company’s vision and model will require an amazing finance team to help Crossover scale to meet the incredible opportunity it is chasing.

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