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In our Decisions at Scale series, we look past headlines and milestones to explore the decisions that shape how companies grow and the insights leaders gain in the process.
Our first story comes from Healthee, an AI-powered platform that helps employees and HR teams navigate healthcare benefits with clarity whose Series B round we recently led.
This spotlight focuses on how conviction, credibility, and precise stakeholder mapping can open doors that most sales teams don’t even try to knock on.
The employer benefits market is tough to break into. Once a large organization is tied to an incumbent vendor, change becomes rare. So when Healthee identified a large financial institution already working with one of the most entrenched players in the market, the default response might have been: “not worth the effort.”
But the team didn’t walk away. As co-founder and CEO Guy Benjamin put it, “They weren’t looking to switch. But they did have pain points, and we believed our product could solve them better.”
The first call didn’t come from a cold outreach. It came through a warm introduction - a trusted connection who knew both sides.
Guy describes it as “credibility by association,” it got Healthee a fair hearing in a market where trust is currency - and it came through Key1, a reminder of how founder–investor partnerships can translate into tangible outcomes.
When the team first learned that the bank was already working with a leading competitor, the choice to stay in the conversation became a turning point.
Rather than see the competitor as a wall, the team treated their presence as proof there was a real need and a chance to show why Healthee could meet it better.
The team later shared the story internally as proof that even deeply entrenched customers can change course when the value is undeniable, and the team has the conviction to pursue it.
In complex enterprise sales, the decision maker isn’t always the most powerful voice in the room. For Healthee, winning over the customer’s broker was the best move.
In long sales cycles, mapping influence is as important as mapping the org chart. Champions come in unexpected roles, and the people shaping opinion often don’t have formal authority.
The Outcome: From Intro to Contract in Two Months
The deal moved unusually fast. Beyond the immediate business impact, it gave Healthee’s leadership team a deeper conviction in their enterprise motion.
As Guy puts it, “It’s not only about having the better product. It’s about being the team that listens, adapts, and makes it easy to say yes.”
In growth-stage markets where competition is fierce and large customers are slow to move, Healthee’s story is a reminder that the biggest opportunities often sit behind the doors everyone else assumes are closed.