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 thrives in SMB — fast cycles, high volume, transactional velocity. You're comfortable with 100+ calls a day and you don't need a 6-month enterprise sales cycle to feel productive.

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 SMB deals at volume — Handle 100+ calls daily with small business owners; 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, automate the mundane, and keep your conversion rate high even at scale

• Expand into new lines — Close across new insurance products as we scale

• You've built a career closing SMB — you understand the mindset of small business owners and know how to earn their trust fast

• You're a closer first — proven track record of closing at high velocity, high volume (100+ calls/day environments)

• You don't lose sharpness at scale — your close rate holds when the call count doubles

• 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 SMB sales — think transactional, short-cycle, high-volume

• This is not an enterprise role; lengthy deal cycles and complex procurement processes are not what we do

• Demonstrated ability to maintain quality and conversion at 100+ calls/day

• 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)

• Background in SMB-focused companies — insurance, fintech, or other regulated industries

• Track record of designing sales playbooks that scale

• Ex-founder experience building and scaling sales teams

• Insurance license

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

• Location: San Francisco, in-office

• Schedule: Monday–Friday, 5 AM–7 PM. This is not a typo. The hours are long. The people who thrive here wouldn’t have it any other way.

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

1. Lead screen — Initial fit and alignment

2. Founder 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.