Leadership, Investment, and Digital Health with Julia Bernstein

I’m excited to introduce my second guest, Julia Bernstein, COO of Brightside Health. With over 15 years of experience in healthcare, Julia has held leadership roles at notable companies such as Thirty Madison, Tempest, Beacon Health Options, and Ginger. In addition to her executive work, she’s an active investor and advisor (including her involvement with Care+Wear !). And most importantly, Julia is a great friend of mine!?

Q: I’m familiar with your impressive story, but I’d love for you to share your background with the audience, including how you reached this point in your career and what initially drew you to the digital health sector –?especially before so many saw it as an opportunity.

A: Sure! I’ve always had a strong interest in science, medicine, and health. I started out as a biology major, but after one challenging quarter, I switched to studying history and religion. Like many liberal arts majors who aren’t sure of their path, I ended up in strategy consulting.

I was fortunate to work on several healthcare projects at McKinsey, including some innovative strategy work with a major payer. I found the work fascinating—we were exploring new business models and technologies—but I also realized that writing PowerPoint presentations and leaving them on someone else's desk wasn’t satisfying to me. I wanted to be more hands-on in creating change. So, I decided to go to business school and transition into an operations role at a startup, with the goal of focusing on healthcare.

In 2012, I was lucky enough to attend Stanford Business School and landed in the Bay Area at a time when companies like Omada Health were just starting to emerge. I managed to talk my way into a business operations role—what we would now call chief of staff—at a company called Ginger.io, which is now part of Headspace Health. I spent the next five years in sales, sales operations, and business development at a few behavioral health and healthcare companies in the Bay Area, including Ginger and Beacon Health.?

This experience gave me a real crash course in disrupting healthcare from the outside in and understanding how the system works. I learned about the intricacies of how providers operate, how payers work, and what it’s like to sell a Medicaid contract. While I loved the work, after five or six years in sales, I found myself, four months postpartum, needing a change. I wanted to move to the operational side of things, have more stability, and also get the chance to build and lead a team.

For the past six years, I’ve focused on operations at a range of direct-to-consumer and direct-to-payer healthcare companies, mostly in New York. I worked at Tempest in the alcohol space, Thirty Madison in men’s and women’s health, and for the past year, I’ve been leading operations at Brightside Health, a telehealth provider offering mental health services across all 50 states. We’re focused on providing life-saving care to individuals 13 and older, through a combination of one-on-one therapy, psychiatry, a suicide prevention program, and an intensive outpatient program. ?I’m also an active angel investor, sit on a few corporate boards, do some advisory work, and I now live in the suburbs with my husband and two kids!?

Q: Can you kind of talk a little more about how you were able to successfully make that transition from sales to operations? I think you've done it in an area where it's actually very difficult to make that kind of a switch.?

A: That’s a great question. I think careers are more like zigzags than straight ladders, so it wasn’t a transition I really planned. It just came about with each new opportunity. Not all sales roles are created equal, and that’s one of the key lessons I learned along the way.

For example, when I was at Ginger and later at Beacon, the sales roles I had were more consultative in nature. We weren’t just pushing quick deals. The sales cycles were long—sometimes 12 to 18 months—and the implementation periods could last a year. So, when I was selling, it wasn’t just about closing a deal—it was more like a 2- to 3-year process. We’d spend time in a state getting to know the providers and the plans. For commercial deals, we’d focus on the commercial side, and for Medicaid deals, I’d be involved in lobbying at the state level.

Once we secured a deal, I didn’t get paid until it went live. That meant I ended up building massive 400-page RFPs, creating economic models, designing staffing plans, and managing the entire implementation process. It was sales, but it was also operational work at the same time. This experience gave me a really solid understanding of how things worked on the ground.

That experience set me up well for transitioning into operations. I was able to leverage the knowledge I gained and ultimately moved into a COO role. The CEO who saw my potential believed in me and gave me the opportunity to step into that leadership position, and I’ve been learning and growing in operations ever since.

Q: As the COO of Brightside Health and with multiple executive roles under your belt, how would you define your leadership approach? What is the best leadership advice you received that helped develop this approach over time????

A: I’d define my leadership approach as "trust but verify." I really believe in hiring skilled people—many of whom are experts in their areas far more than I am, given the breadth of my role. My job is to set them up for success by giving them clear expectations, offering support when needed, and trusting them to do their work. If I have concerns, I’ll ask questions, but otherwise, I try to let them take ownership and succeed. I believe in adjusting the level of support based on the situation.

It’s taken me some time to get to this point. I’ve been fortunate to have some incredible bosses, mentors, and now friends, who’ve shaped my approach. Early on in my health tech career, I worked for Karan Singh. Karan was a great example of how a leader should present themselves—calm under pressure, knowing what to get upset about (which is often not much!), and how to keep things in perspective. That’s a lesson I carry with me.

I was also lucky to work with Briana Duffy, now President for Carilion Behavioral Health. Briana has a unique ability to combine directness with empathy in her leadership style, and that's something I’ve tried to integrate into my own approach.

In the end, a lot of leadership is about learning by doing—figuring out what works for you and what resonates with others. And having had great mentors and bosses has been invaluable in helping me shape my style over time.

Q: As an angel investor in healthcare startups with an impressive portfolio, what key factors or qualities set the successful startups apart from the rest? What advice would you offer to founders in digital health seeking investment or who have just started out?

A: Care+Wear was our first investment, and I’ve learned a tremendous amount from it. It’s taught me a lot about being a better operator, how to approach investing, and I’ve also had the opportunity to participate in programs like AngelTrack.?

At this point, my biggest question for any founder is, "Do you understand how you’re going to get paid?" Because, while there are a lot of brilliant and passionate people in healthcare with great ideas who see a problem and want to fix it, we operate in a very complex system. The flow of funds is often confusing, and understanding not just the pain point and the solution, but also who’s going to pay for it and whether they have the means to do so, is absolutely critical. This is something I’ve learned to really probe and test when I evaluate and work with companies.

The other thing I’d mention is that I’m writing small checks. They won’t be life-changing amounts of money, but they come with support—whether through a formal advisory role, a board seat, or even informally. Most of the investments we make, which my husband and I do together (he’s not a healthcare guy, but I’ve trained him enough at this point that he could probably play one on TV), are in companies where we believe we can add value. His experience with deals and contract negotiations, combined with my background in healthcare and pattern recognition from having made over 20 investments (including companies I’ve worked for), is where we think we can make a real difference.

So, for me, it’s about understanding what problem the company is solving, how they plan to get paid for it, and how I can add value to help my investment go further.

Q: You’ve witnessed the evolution of digital health over the past 15 years. What do you consider to be the most significant change during this period, and what trends have emerged along the way that you see have the potential to create more change?

A: I think the biggest change I’ve seen in the last 15 years is the increasing consumer willingness to embrace new modalities of care. When I was at Ginger, we’d walk into meetings with a pitch deck that literally had a slide saying, "Your smartphone is your life’s diary." We were trying to convince people that smartphones could be a useful tool for healthcare. Fast forward, and smartphones are ubiquitous. Then we had to convince people about telehealth, and now we’re talking about AI-powered telehealth and other innovations.

So, the biggest change has been how open people are to accepting new ways of receiving care. It’s been amazing to watch how something that felt foreign or far-fetched 10 or 12 years ago is now fairly commonplace. I hope that regulation will continue to evolve alongside these innovations, especially as a telehealth advocate, but it’s been exciting to see how the landscape has shifted.

Looking ahead, I think AI is a big trend—though it's definitely a buzzword at this point. But the idea that software infrastructure can make care more efficient and effective is a powerful one. It’s something I think about a lot, both in terms of improving administrative tasks and how to make my nonclinical staff more efficient, as well as helping clinicians be more successful.

I’m also optimistic about the new wave of interventional treatments coming down the pipeline—whether it's cancer vaccines, new TMS protocols, or other advances. We’ve already seen incredible innovation, both in digital tools and in medical treatments, and I think that trend will continue to drive significant change in healthcare.

Q: I often discuss the importance of maintaining the human touch as technology advances. How do you see digital health companies maintaining the essential human connection? What strategies do you believe are crucial for achieving this balance??

A: At the core of healthcare, it’s about people. We see individuals on their worst days, but also on their best days. Our goal is to make their bad days a little brighter and help them feel seen and supported on their good days. This is something we think a lot about at Brightside when it comes to using technology.

We leverage AI, chatbots, and automation for simple customer service tasks, but always with the goal of having a human available to pick up the phone within 60 seconds if someone has a question. It’s easy to forget how much the basics matter—sometimes, just a simple, human touch goes a long way.

For example, one of my clinical leads developed a program called BrightNotes, where we send personal notes to patients who have experienced significant life events, just to let them know we’re thinking of them. It’s a small gesture, but it helps maintain that human connection.

Looking ahead, my word for 2025 is "integration." It’s about further integrating physical health with behavioral health, blending telehealth with in-person care, and incorporating technology into care without the mindset that it has to be either/or. Finding that balance will be key to maintaining the human connection as we move forward.

Thank you Julia for spending the time to share you insights with us!!