Founding Account Executive

Harper • San Francisco, CA

3d • $75,000 - $125,000 • Onsite

About The Position

We're on the frontier of building an AI-native professional services company. We're building the best AI commercial insurance distribution engine for scale.
The Problem
36 million businesses in America need insurance. It's not optional—regulations require it, contracts demand it, landlords won't lease without it. Yet the industry is broken.
77% of small businesses are underinsured. 40% have no coverage at all. Most don't even understand what their policies cover. They're running with risk because the distribution system failed them—too slow, too opaque, too confusing to navigate.
Over 90% of commercial insurance distribution is still human-led. The same manual process as 30 years ago—just with email instead of fax. Every policy requires dozens of complex decisions and hundreds of steps. Two-week processes that should take hours. Everyone hoping someone gets it right.
We're building the inverse: 90%+ AI-led, inching toward the higher 90s. Not by patching the existing system with basic automation—by building something fundamentally different where humans and AI seamlessly collaborate to execute complex workflows at unprecedented speed.
The Thesis
Every industry with human-bounded distribution consolidates rapidly once someone makes it computational. Search had thousands of engines until Google made ranking computational. Ride-hailing was fragmented until Uber made dispatch computational.
When distribution becomes computational, Jevons Paradox kicks in: increased efficiency leads to increased consumption. Better search didn't mean less searching—it meant vastly more. Cheaper rides didn't mean fewer trips—it meant transportation for use cases that never existed.
Insurance will follow the same pattern. When getting the right coverage becomes fast and frictionless, the 77% of underinsured businesses will finally get properly protected. The market expands, not contracts.
We're building the engine that makes that happen. You'll be the closer who proves it works—and the architect who makes it scale.
The Role
You're a hardcore closer who can sell ice to an eskimo. But you're also obsessed with building scalable, automated sales systems. You don't just follow processes—you transform them, making teams 10x more effective.
This is a founding role. You'll close deals and drive revenue 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.
You'll work directly with the founders. There's no committee. No approval chain. You close it, you build it, you own the outcome. While you'll be selling insurance products to businesses, you don't need to be an insurance expert on day one—we'll teach you the rest.

Requirements

• Proven track record of building and running high-performance sales at unprecedented speed
• Experience turning sales intuition into scalable automated systems
• Comfort with high-velocity environments where everything changes daily
• Ability to leverage AI tools for sales automation and workflow improvement
• Based in San Francisco (or willing to relocate)
• Willingness to obtain required insurance licenses within first 90 days

Nice To Haves

• Ex-founder experience building and scaling sales teams
• Background in insurance, fintech, or other regulated industries
• Experience with AI-assisted sales tools and automation
• Track record of designing sales playbooks that scale

Responsibilities

• Close deals. This is the core. You're the closer driving revenue. Master the playbook by end of week one, then improve it by week two. Measure success by deals closed and revenue generated, not hours worked.
• Build AI-assisted sales systems. Use AI to eliminate 95% of friction from lead-to-close workflow. Leverage AI for crafting pitches, automating lead generation, and building qualification workflows. Bridge the gap with AI tools until permanent automation is built.
• Transform the sales engine. Identify critical bottlenecks and launch AI-human workflows that improve throughput. Turn sales intuition and decision-making into scalable automated systems. Create processes that don't require additional headcount to scale.
• Design for rapid expansion. Build sales systems for new insurance lines. Create and continuously enhance playbooks that get smarter over time. Work closely with engineering to test AI solutions and provide rapid feedback.
• Question everything. If someone says "that's how insurance sales works," that's exactly where you start. The fastest sales process is no process. Every step must justify its existence. Make it smarter. Speed compounds.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed