Enterprise Account Executive — Insurance AI (Seed-stage)

Enterprise Account Executive

Snapshot: $90K–$150K base

• $200K–$330K OTE + equity
• San Francisco
• On-site (5 days when not traveling)
• No visa sponsorship
• 3–10 yrs enterprise closing

THE OPPORTUNITY

Our client is a seed-stage, venture-backed AI company (:10 people) rebuilding how insurance brokerages operate — automating complex workflows across commercial, personal, and employee-benefits lines. They've processed over $1B in premium flow and achieved 15x+ revenue growth since launching last year, inside a $400B+ industry.

This is a pure-hunter enterprise role: you'll own the full cycle and close the largest insurance brokerages in the US, working directly with leadership and product.

What You'll Do

Own the entire sales cycle from cold outreach to signed contract for enterprise accounts. Travel consistently for on-sites, conferences, and dinners to build relationships and close face-to-face. Run consultative, relationship-based sales in a historically traditional industry. Help evolve the enterprise sales playbook alongside leadership and product.

Manage and expand relationships post-sale to drive expansion revenue.

What Success Looks Like

First 90 days: learn the product and brokerage buyer, build a travel-driven pipeline, and advance early enterprise deals. First year: consistently close large brokerages, sharpen the playbook, and build durable expansion relationships.

MUST-HAVES

3–10 years closing B2B software deals to enterprise accounts; comfort with heavy travel and in-person selling; a scrappy, self-driven approach.

NICE-TO-HAVES

Insurance, insurtech, or fintech experience; a background selling into brokerages or traditional industries; founding/early-AE experience.

Compensation & Benefits

$90K–$150K base (USD), $200K–$330K OTE, competitive equity.

LOCATION & WORK MODEL

On-site in San Francisco, 5 days in office when not traveling. Consistent travel expected.

HIRING PROCESS

Initial screen with a company leader (15–30 min) → take-home exercise → on-site team interview (:1 day) → conversation with CTO & GTM advisor (30–60 min) → references.

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.