Job Details

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 100xsince 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.

What You'll Do

• 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 Might Be a Fit If...

• 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

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 Have

• 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

Compensation

• Salary: $185,000-$250,000 + performance bonuses & equity
• Location: San Francisco, in-office
• Schedule: Monday-Friday, 5 AM - 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.

Benefits

• Health, dental, and vision insurance
• Commuter benefits
• Team meals and snacks

The Process

1. People screen - Initial fit and alignment
2. Founder screen - Skills and culture fit
3. 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.