Founding Enterprise Account Executive — Insurance AI (Seed-stage)

Founding Enterprise Account Executive Snapshot: $125K–$170K base · $230K–$340K OTE (50/50) + equity · San Francisco (primary), NYC, or Chicago · Hybrid (2–3 days in office) · Visa sponsorship available · 3–8 yrs closing experience THE OPPORTUNITY Our client is a seed-stage, venture-backed AI company (~16 people) building the "AI Analyst" for insurance P&L and actuarial teams — automating the compliance and data work that eats 30%+ of their week. Early traction is exceptional: a 100% head-to-head win rate against legacy competitors and 80% of POCs converting to paid, inside a $6 trillion market. This is a true founding sales hire: you'll build the enterprise motion from scratch and partner directly with the founder CEO to close six-figure deals with the largest insurance carriers in the country. WHAT YOU'LL DO Own your pipeline end to end — outbound sourcing (~85% outbound), discovery, demos, and closing $200K+ deals. Build the sales playbook and GTM processes as the founding sales hire. Take over the full sales lifecycle from the CEO (30–60 day cycles). Drive expansion (a recent customer rolled out to 400+ users within months). Navigate multi-stakeholder deals with chief actuaries, heads of product, and P&L owners. WHAT SUCCESS LOOKS LIKE First 90 days: ramp on the product and ICP, take over live deals from the CEO, and build a self-sourced pipeline. First year: own and hit an enterprise number, codify the repeatable playbook, and lay the groundwork for the sales team that scales behind you. MUST-HAVES 3+ years closing B2B SaaS at startups with $200K+ ACV; at least one year of enterprise closing; startup grit and comfort selling to senior, technical buyers. NICE-TO-HAVES Experience in insurance, fintech, or another regulated industry; a track record as an early/founding AE; consultative, multi-threaded enterprise deal experience. COMPENSATION & BENEFITS $125K–$170K base (USD), $230K–$340K OTE on a 50/50 split, competitive equity, visa sponsorship available. LOCATION & WORK MODEL Hybrid, 2–3 days in office. San Francisco (primary); New York (hybrid once the office opens); Chicago (remote). HIRING PROCESS Recruiter screen (20 min) → hiring-manager screen (45 min) → product demo / working session (40 min) → onsite (4 parts, ~3 hrs). ABOUT THIS SEARCH This is a confidential search managed by our recruiting team on behalf of our client. We've kept the company name off the posting — apply and we'll share full details and introduce you directly. We're an equal-opportunity partner and welcome applicants of all backgrounds; compensation reflects the role's posted range.