Founding Account Executive

Harper•San Francisco, CA

3d•$100,000 - $200,000•Onsite

About The Position

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll be the closer who proves it works—and the architect who makes it scale. The Thesis This is a founding role. You’ll close deals from day one, but you’ll also build the sales infrastructure that lets us scale without adding headcount. Every workflow you design, every AI-assisted system you create, every playbook you write becomes company DNA. Winning in 6-12 months means revenue growth AND a sales engine that runs itself. The Role You’re a hardcore closer who could sell sunscreen in a snowstorm. But you’re also obsessed with using AI tools to close faster and providing the feedback that makes those tools better. You work directly with founders. No committee. No approval chain. You close it, you build it, you own the outcome. You don’t need insurance expertise on day one—we’ll teach you.

Requirements

Proven track record in high-velocity sales
Experience turning sales intuition into scalable systems
Comfort with environments where everything changes daily
Ability to leverage AI tools for sales automation
Based in San Francisco or willing to relocate
Willingness to obtain required insurance licenses (we’ll pay for training and licensing)

Nice To Haves

Ex-founder experience building and scaling sales teams
Background in insurance, fintech, or regulated industries
Track record of designing sales playbooks that scale
Insurance license (we’ll pay for training and licensing for the right candidate)

Responsibilities

Close deals — Master the playbook by week one, improve it by week two; measure success by revenue generated
Use AI tools to close faster — Leverage AI to eliminate friction and increase your velocity
Provide feedback that improves the tools — Your insights from live calls make our AI smarter
Expand into new lines — Close across new insurance products as we scale