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Go-to-Market Growth Lead

Harper (YC W25), San Francisco, California, United States, 94199

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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 run the floor that proves it works. The Thesis Think of it like running a market-making desk—your team takes in risk (leads, deals, customers) and services it. The better your systems, the more volume you can run, the more money everyone makes. The goal is simple: hit higher and higher automation metrics. The more your pod automates, the more deals you can run, the more you all get paid. The Role You’ll lead a high-volume sales floor. You own closing—you’re on the phone getting deals done. But you’re also working with your pod (FDE, intake, service, submission) to build the machine that feeds you better deals and handles everything around the close. You’re not coordinating from above. You’re in the pit, closing and building. What You’ll Do Run the floor — Lead a pod across the full funnel: intake → submission → service → close Build products with your team — Work with your FDE to ship voice AI, workflow tools, submission automation Hit automation metrics — Push toward 100% automation on repeatable tasks Own your verticals — Build expertise across sectors; develop playbooks your whole team runs Drive top-of-funnel GTM — Use sales feedback to optimize demand gen Close deals — This is your primary function; set the standard for call quality and close rate You Might Be a Fit If…

You want to run something—a floor, a team, a P&L You can translate customer objections into product fixes by end of day You see sales and GTM as one system You thrive in high-volume, high-intensity environments You want team upside, not just individual commission You can close—high-volume sales experience, handle objections, get deals done Requirements

Proven track record in high-volume sales or sales leadership Experience leading teams across multiple functions Ability to translate customer conversations into product/process improvements Comfortable working with engineers to spec and ship automation Based in San Francisco or willing to relocate Nice to Have

Insurance, fintech, or regulated industry experience Sales operations or revenue operations background Familiarity with AI/automation tools in sales Experience building playbooks that scale Compensation

Salary: $200,000 OTE (base + team-based bonus & equity) Variable/Commission: Team-based bonus, PE/IB style 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 want to run a floor, close deals, build products with engineers, and work with a team that actually operates like a team—send your resume and tell us about the last system you built. Compensation Range: $135K - $200K

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