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. In 6-12 months, you’ll have built a repeatable recruiting machine AND filled critical roles yourself.

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 — 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’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

• 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

• 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

• Salary: $125,000–$185,000 + 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.