Recruiting Lead

Harper•San Francisco, CA

15h•$185,000 - $250,000•Onsite

About The Position

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—and you’ll think about what we need 24 months from now, not just today’s reqs. In 6-12 months, you’ll have built a repeatable recruiting machine that can handle 10x growth AND filled critical roles yourself. This is execution AND strategy. 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.

Requirements

6-10 years in recruiting, with experience scaling through rapid growth (Series A-C)
2+ years managing recruiting teams of 3+ people
Technical recruiting background strongly preferred
Experience building recruiting processes and systems that survive 10x growth
Ability to source, sell, and close directly—not just manage
Deep understanding of technical roles and talent landscape
Based in San Francisco or willing to relocate

Nice To Haves

Experience at companies that scaled from 30 to 200+ (not just repeated Series A stints)
Background recruiting for AI-native or technical sales organizations
Employer brand and recruiting content experience
Experience building recruiting teams from scratch

Responsibilities

Close candidates yourself — Sourcing, screening, selling, closing engineering and GTM roles
Build recruiting infrastructure for 10x scale — Repeatable sourcing strategies, structured interviews, calibrated scorecards that don’t break when we triple headcount
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; think 24 months ahead
Build and lead a team — Hire and manage recruiters as we scale; set the bar for performance and velocity