Founding Account Executive
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 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.
What You’ll Do
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 Might Be a Fit If…
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
Requirements
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)
Nice to Have
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
Compensation
Salary: $100,000–$200,000 + performance bonuses & commission
Location: San Francisco, in-office
Benefits
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
The Process
People screen — Initial fit and alignment
Lead screen — Skills and culture fit
Super day — See how you operate in real time
To Apply
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.
