Recruiting Lead

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.

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.

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.

• 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

• You’re a closer with a technical background (years recruiting engineers)

• You’ve scaled recruiting through rapid growth phases—not just early-stage setup, but the ebbs and flows of Series A through C

• You’ve built systems, not just filled roles—and you think about what breaks at 10x

• You have tenure and depth (2-3 year in-house stints where you saw real scale)

• 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 and build a team under you

• 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

• 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

• Salary: $185,000–$250,000 + performance bonuses & equity

• Location: San Francisco, in-office

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

1. People screen — Initial fit and alignment

2. Founder screen — Skills and culture fit

3. Super day — See how you operate in real time

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.