Founding Account Executive
Harper, San Francisco, CA, United States
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. What You’ll Do
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 Might Be a Fit If…
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
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 Have
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)
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
Founder 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.
#J-18808-Ljbffr
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. What You’ll Do
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 Might Be a Fit If…
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
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 Have
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)
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
Founder 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.
#J-18808-Ljbffr