Recruiting Lead

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. To do that, we need to assemble one of the highest-caliber teams in the industry. That’s where you come in. The Thesis You’ll be Harper’s first dedicated recruiting hire—building the talent function from the ground up while closing candidates yourself. You’ll build the systems that let Harper scale from 30 to 100+ without creating chaos. In 6-12 months, you’ll have built a repeatable recruiting machine AND filled critical roles yourself. The Role This isn’t a coordination role. You’re sourcing, selling, and closing exceptional people across engineering, sales, and GTM. Technical recruiting background preferred—you understand tech stacks, know which competitors to pull from, and have a developed mind map of the landscape. You work directly with founders. No committee. No approval chain. You source it, you sell it, you close it. What You’ll Do Close candidates yourself — Sourcing, screening, selling, closing engineering and GTM roles Build recruiting infrastructure — Repeatable sourcing strategies, structured interviews, calibrated scorecards Own technical recruiting — Understand the tech stack; evaluate whether an engineer is actually good Expand into GTM and operations — Once technical recruiting runs, build pipelines for sales/marketing/ops Partner with founders on hiring strategy — Push back when job specs don’t make sense You Might Be a Fit If… You’re a closer with a technical background (years recruiting engineers) You’ve built systems, not just filled roles You have tenure and depth (2-3 year in-house stints) You move at founder speed—close great candidates this week, not next month You can sell a trading floor culture (intense, loud, collaborative) You’re ready to own the function Requirements 4-8 years in recruiting (6-8 preferred) Technical recruiting background strongly preferred Experience building recruiting processes and systems Ability to source, sell, and close directly Deep understanding of technical roles and talent landscape Based in San Francisco or willing to relocate Nice to Have High-growth startup experience (Series A/B) Background recruiting for AI-native or technical sales organizations Employer brand and recruiting content experience Some people management experience Compensation Salary: $125,000–$185,000 + performance bonuses & equity 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 Founder screen — Skills and culture fit Super day — See how you operate in real time To Apply: If you’ve built recruiting infrastructure that scales and can close technical talent others can’t reach—send your resume and tell us about the hardest role you ever closed. Compensation Range: $125K - $185K #J-18808-Ljbffr Harper (YC W25)