Enterprise Account Executive

Insurance brokerages lose an estimated $130B each year to manual work — reviewing policies page by page, rekeying data between systems, and pushing paperwork that should have been automated a long time ago.

Coverflow is the AI platform changing that. We plug directly into brokerage systems to automate the workflows that eat up thousands of hours every year — across commercial, personal, and employee benefits lines.

We've processed over $5B in premium flow, grown revenue more than 15x since launch, and are backed by AIX Ventures, Founder Collective, and Afore Capital. Leading regional and national agencies already trust us with thousands of policies every week.

We're hiring an enterprise AE to own the full sales cycle into the biggest brokerages in the country — top 100 firms. Five- and six-figure contracts, multi-stakeholder buying committees, executive alignment, and structured procurement cycles.

You’ll drive outbound, build executive relationships, navigate complex procurement, and work hand-in-hand with product to turn feedback into features. You’ll also help shape our enterprise sales playbook as we scale.

This isn’t shelfware. Our platform saves real hours for real people, and you’ll be a trusted advisor helping brokerages modernize how they operate.

3+ years closing B2B software deals at the enterprise level with a real track record against quota. Experience selling $100K+ ACV through consultative, relationship-driven cycles. You learn fast, communicate clearly, and aren’t afraid of ambiguity. Insurance or fintech background is a plus. Early-stage startup experience is a bonus. We need a hunter.

$300K+ OTE with uncapped commission. Full medical, dental, vision, and 401(k). Team lunches, transportation stipend, and regular off‑sites. In‑person in San Francisco. Must be authorized to work in the U.S.