Founding Account Executive

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.

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.

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.

• 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

• You’re a closer first—proven track record of closing at high velocity

• You’re obsessed with systems—you figure out how to 10x team effectiveness

• You leverage AI strategically (crafting pitches, building automated qualification workflows)

• You think in first principles and build complex systems in one-third the normal time

• Ex-founders are a plus

• 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)

• 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)

• Salary: $100,000–$200,000 + performance bonuses & commission

• Location: San Francisco, in-office

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

1. Founder screen — Initial fit and alignment

2. Lead screen — Skills and culture fit

3. Super day — See how you operate in real time

If you’re excited about building something massive and owning a meaningful piece of it—send your resume and tell us about the last sales system you built or broke.