Entry Point: I joined Gravie right after their Series B fundraising as the Head of Demand Generation Marketing.

Needs: Gravie reinvented how health insurance works in the US. No small feat! In order to accelerate growth, I was hired to build pipeline for the core small/medium sized business health insurance offering. This is a category that has lots of pain and cost friction, but often a buyer persona that isn’t well-informed of options outside the status quo small group plans.

Team: CMO, Head of Demand Generation (me), marketing managers (2), and Sales Development Representatives.

Focus areas: Because the market was wide, horizontal, seasonal, and under-informed, we focused on outbound, organic inbound, and regional events, and some PR.

Positioning. We also went through a re-positioning spring for website redesign and a core set of informational videos.

Marketing-led Outbound. I worked closely with the founders to build the first Sales Development Representative team. My role in that was hiring, training and coaching, as well as setting up the CRM-outreach tools and reporting. With a great, eager, small group we were able to scale quite well.

Inbound. We also applied Hubspot and worked with a content partner to develop organic inbound.

Events. Our regional event strategy was aligned with a new product strategy. This meant getting out into

PR. The team also won a Silver Quill Award for Public Relations impact, specifically related to market expansion. We made a splash in Boston newspapers too after “deflategate.”

Business Results:

I was brought in for board meetings on a quarterly basis to showcase our progress. We scaled to a repeatable, predictable CAC and meeting volume.

Gravie has proceeded to continue to grow rapidly, with multiple product lines, scaled national growth, and over $463M in fundraising as of June 2026.

If you want to get deeper into results with this privately-held business, I’m happy to put you in touch with the leadership team.