7 Go-to-Market Lessons From Building a $150M Mental Health Platform

When Brad Kittredge talks about getting Brightside’s first national insurance contract, he doesn’t mention months of negotiations or formal pilot programs. Instead, he describes walking into Cigna with a 30-page report and saying: “Here are the results of the pilot you guys didn’t know you were doing with us.”

In a recent episode of Category Visionaries, Brad Kittredge, CEO & Co-Founder of Brightside, shared the unconventional strategies that took his virtual mental health platform from zero to 135 million covered lives. His journey offers a masterclass in navigating regulated markets, breaking through credibility barriers, and building defensible differentiation in crowded categories.

Here are seven go-to-market lessons that matter for founders building in complex, regulated industries.

1. Build Your Differentiated Thesis Before You Build Your Product

Brad didn’t start coding on day one. He started by identifying where the entire market was getting it wrong. While everyone else was talking about access and treating mental health care as a commodity, Brad saw a different problem: “Everyone talking about access, we’re sort of treating mental health care as a commodity, acting we just need more appointments, and if we have more appointments, we’ll solve this problem.”

His contrarian insight: “If we take that same crappy care that I saw at a great health system and move it online, we’re not solving the problem. What we need is to use this transition from traditional care to virtual care as an opportunity to remake them all from the ground up.”

This thesis did two things. First, it gave Brad a compelling story to recruit exceptional co-founders who were otherwise happy in their roles. Second, it created a foundation for differentiation that would matter later when competitors flooded the market.

The lesson: In crowded markets, you need more than a product thesis. You need a market thesis that explains why everyone else is solving the wrong problem. Spend time refining this before you write a line of code.

2. Know Exactly What You Need to Prove First

Brad faced skepticism from nearly everyone he pitched in 2017. This was pre-pandemic, when telemedicine adoption was in single digits. He remembers clearly: “I had been trying to pitch it in parallel and a lot of people said, I don’t know if consumers are going to be comfortable with that. I don’t think someone would choose to like see a doctor online that way.”

Rather than trying to prove everything at once, Brad focused on the single most important assumption: would consumers actually use remote mental health care? His CTO Jeremy started writing code in September 2017. They launched their alpha in January 2018. Within a week, they had their first revenue.

“Within two days of maybe putting up our site with no ad spend or maybe $100 of ad spend, we got our first purchase. And so Jeremy got a text message on his phone with the stripe verification of a charge and he kept that screenshot. And the feeling that we had when that happened was like, oh man, this is real. This is going to work.”

The lesson: In regulated industries, you can’t move fast and break things. But you can move fast on proving your core assumptions. Identify the one thing that needs to be true for your business to work, and build the minimum to prove it.

3. Turn Cash Customers Into Data Assets for B2B Sales

Brad recognized early that Brightside faced a classic chicken-and-egg problem. Most people want to use their insurance for healthcare, but insurance companies won’t contract with unproven startups. His solution was elegant: “We decided that the strategy we might take is to start by accepting cash and that we can get customers that way, and that the way to build credibility was going to be with data. Instead of just going and telling people what we can do, let’s go show them with the data.”

The execution was strategic. Even while charging cash, Brightside collected insurance information from every customer. When they had 500 members with Cigna insurance who had been customers for at least three months, Brad made his move: “We analyzed all the data and turned it into like a 30 page report with a bunch of, you know, charts and takeaways and insights. And then I just went knocking on every door I could find at Cigna.”

The positioning was brilliant: “Because a lot of healthcare companies get stuck in pilot purgatory. And I didn’t want them to even suggest that’s how we start together.”

The lesson: In B2B markets with long sales cycles, your early customers can be more valuable as proof points than as revenue sources. Design your go-to-market strategy to build data assets that enable enterprise sales, even if you start with a consumer model.

4. Let Unit Economics Drive Your Revenue Model Evolution

Brad’s move from cash to insurance wasn’t just about market size. It was about unit economics: “More people are going to want to pay with their insurance. And when you think about the value proposition, if you’re going to get healthcare, whether you’re going to pay out of pocket or pay with your insurance, obviously your out of pocket cost is just way lower with your insurance.”

This created a clear hypothesis about acquisition costs: “That translates back into this assumption or thesis that we could acquire those customers for a much lower acquisition costs, that our CAC would be much lower, and that our CAC to LTV ratio would be much more attractive inside the insurance networks rather than cash outside.”

The thesis proved out: “We have dramatically lower acquisition costs because of the value proposition when we can accept someone’s insurance, we have a great LTV with insurance and great unit economics and revenue dynamics.”

The lesson: Revenue model decisions should be driven by clear hypotheses about unit economics, not just market size or ease of implementation. Map out how each model affects CAC, LTV, and the ratio between them.

5. Follow the Cost Curve to Find Your Wedge

As competitors entered the market, Brad faced a differentiation crisis: “We still found when were going to talk to payers and that we had many other competitors enter the market in that interim, that people were having a hard time telling us apart from everybody else, saying, like, everybody talks about quality, everybody says they’re great and that they can offer more access.”

His solution came from analyzing where value really lived: “It’s true for many conditions in the healthcare industry, and very much so for mental health care, that the distribution of costs within a patient population is very uneven. So you’ve got a small portion of people that have more complex, severe, or acute conditions driving a massively disproportionate share of the total costs of that population.”

This led to a counterintuitive decision: build a crisis care program for suicide prevention—exactly the kind of high-risk, complex cases that competitors were avoiding. Brad explains his thinking: “To me, that was just really planting a flag, saying, we are going to be the best at treating the hardest cases. We’re not going to shy away. We’re going to do the hard work. And that’s how we’re going to differentiate from everybody else in the market.”

The competitive moat was clear: “I don’t think anybody else has the DNA to want to follow us in doing this and doing this really hard work and impactful work.”

The lesson: In mature markets, differentiation often lies in solving the problems everyone else is avoiding. Follow the cost curve to find where the real value creation happens, even if it’s harder to execute.

6. Force Yourself to Learn Your Non-Intuitive Skills

Brad is refreshingly honest about his early mistakes: “When I look back at what I’ve been good at and not good at, the early marketing is probably what I was not good at.”

The problem was natural tendency: “When I had items on my to do list that were either like some product or design work or some marketing work, I naturally gravitated towards the product tasks and the marketing tasks kind of stayed on my to do list because they were harder, they were less intuitive to me.”

In hindsight, he wishes he’d done things differently: “I should have and wish I had, or if I could do it over again, would lean much more into forcing myself to accelerate my marketing learning curve, to get much more adept at that sooner and really understand our funnel instrumentation and our sort of Adwords process to be able to drive better results sooner there.”

The lesson: Your natural inclinations as a founder will create blind spots. Identify the critical skills that don’t come naturally and force yourself to develop them early. The tasks that stay on your to-do list longest are often the ones that matter most.

7. Understand That Regulatory Risk Is Existential Risk

Brad takes regulatory risk seriously because the stakes are different than other business risks: “Any Founder operating in a regulated industry needs to think about those things, because those are things that. Where you have existential risk, right? Most of your risks are things that might, you know, accelerate your growth rate or diminish your growth rate. But regulatory risk can, like, put you out of business overnight if you are on the wrong side of it.”

His approach was to make conservative choices where it mattered most. For example, Brightside chose not to prescribe controlled substances like benzodiazepines or stimulants, even when it was legally permissible: “We made a decision from a clinical and a safety standpoint. Even when that was very easy and straightforward online, we chose not to do it for what I think are some pretty obvious reasons. And so we’re not exposed to the regulatory risk there.”

The lesson: In regulated industries, some decisions aren’t about maximizing short-term growth—they’re about surviving long enough to build the business you want. Identify where regulatory risk could be existential and make conservative choices there, even if they limit growth in the near term.

The Throughline

What connects these lessons is a pattern of strategic thinking that separates companies that break through from those that get stuck. Brad didn’t just build a better product. He built a differentiated thesis, proved it incrementally, turned customers into sales assets, followed the money to find his wedge, and made decisions that balanced growth with sustainability.

The result isn’t just a successful company. It’s a playbook for navigating the unique challenges of regulated markets—where credibility is currency, differentiation is survival, and the willingness to do hard things creates lasting competitive advantage.