Why the first move isn't a strategy deck
About this piece
These notes draw from ten years inside health insurance distribution and insurtech — across distribution, product, and growth roles — including a national FMO producer onboarding completed as a licensed agent in 2026, and a post-acquisition DTC buildout at a health insurance distribution business. On that build: funnel design, conversion optimization, and the product side of an AI/ML plan recommendation engine for the consumer channel. DTC became the highest growth contributor as the company scaled from $5M to $40M ARR.
The dinner was going well until a firefighter walked in. Full gear, full performance — the kind of unexpected moment that makes a room of strangers actually look at each other. We laughed. We relaxed. And then the conversation turned to DTC, and everyone went quiet again.
That contrast stayed with me. A room full of insurance professionals, comfortable enough to cheer for a firefighter, suddenly careful and coy the moment someone raised direct-to-consumer distribution. Everyone had a view. Nobody would say it plainly.
That's when I knew the strategy wasn't really on any slide deck.
The setup
I'd spent some time in insurtech across distribution, product, and growth roles at companies building the consumer side of health insurance. I came from the VC-backed side of the industry: fast-moving, experiment-driven, roughly 80% of colleagues who had never worked in traditional insurance before.
This time round, it is different. My title was new to the organization. My role was unclear to everyone. I know this because a VP from another team emailed me in the first few weeks to ask: "What is your role in the company?"
What the dinner was actually about
The coyness around DTC wasn't resistance to growth. It was something more specific: a belief, held deeply and quietly, that insurance needs to be sold — not bought. Their families had agents. Their friends had agents. The idea that a customer could navigate coverage alone felt not just unlikely but slightly irresponsible.
What I kept explaining was simpler than they expected. DTC isn't a replacement for agents. It's a lead generation channel. Performance marketing gets the customer to raise their hand. A human still picks up the phone.
Where the real authority sat
The person who sent me that email was a peer on the org chart. In practice, she controlled the thing that mattered most: institutional credibility over what we could and couldn't do.
Our compliance standoff came down to one distinction that took weeks to establish:
- What we called "experiments" were changes to UX and UI — not regulated text.
- I'm a licensed agent across 41 states — I knew exactly where the lines were.
- Her concerns weren't obstruction — they were information about our actual customers.
So I invited her into our weekly calls. Not as oversight — as a contributor. She was closer in age to our actual customer than anyone on our team. She caught things we missed. She asked questions that made our assumptions visible.
"She went from quiet and assessing to actively contributing — not because I managed her, but because I actually needed her."
Over three years, DTC became the highest growth contributor as the company scaled from $5M to $40M ARR. That didn't happen despite the agent channel veterans in the room. It happened partly because of them.
What AI gets wrong about insurance
Everyone is saying AI is the new DTC — that smarter recommendations and faster enrollment will finally remove the human from the loop. I don't think that's right. I have two kids. I know what it feels like to sit with a health insurance decision that actually matters — where the wrong choice isn't an inconvenience, it's a crisis. That conversation still needs a human. Not because the technology isn't good enough. Because trust isn't a feature you can ship.
Three things I believe after a decade of building this from the inside:
- Tech enables coverage solutions — it doesn't replace the humans who explain them.
- Shopping malls didn't disappear when e-commerce arrived. Agents won't either. The company that survives is the one that meets the consumer where they are, and not dictate how consumers should be spending their money.
- Reading the room is the highest-leverage operator skill in a licensed, regulated, relationship-driven industry — more than any growth playbook.
The operators who build the next generation of health insurance distribution will be the ones who can run a performance marketing funnel and earn the trust of a compliance VP — sometimes in the same week.
"I still have good relationships with the original team. Many have moved on. Some things are best solved over a good glass of Chardonnay."
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