Recruiting Lead at Harper (W25)
$125K - $185K  •  0.01% - 0.10%
AI-native commercial insurance brokerage
San Francisco
Full-time
US citizen/visa only
3+ years
About Harper
About the role

We're on the frontier of building an AI-native professional services company. We're building the best AI commercial insurance distribution engine for scale.

The Problem

36 million businesses in America need insurance. It's not optional—regulations require it, contracts demand it, landlords won't lease without it. Yet the industry is broken.

77% of small businesses are underinsured. 40% have no coverage at all. Most don't even understand what their policies cover. They're running with risk because the distribution system failed them—too slow, too opaque, too confusing to navigate.

Over 90% of commercial insurance distribution is still human-led. The same manual process as 30 years ago—just with email instead of fax. Brokers playing phone tag with underwriters. Customers chasing quotes for weeks. Everyone hoping someone gets it right.

We're building the inverse: 90%+ AI-led, inching toward the higher 90s. To do that, we need to assemble one of the highest-caliber teams in the industry. That's where you come in.

The Thesis

Every industry with human-bounded distribution consolidates rapidly once someone makes it computational. Search had thousands of engines until Google made ranking computational. Ride-hailing was fragmented until Uber made dispatch computational.

When distribution becomes computational, Jevons Paradox kicks in: increased efficiency leads to increased consumption. Better search didn't mean less searching—it meant vastly more. Cheaper rides didn't mean fewer trips—it meant transportation for use cases that never existed.

Insurance will follow the same pattern. When getting the right coverage becomes fast and frictionless, the 77% of underinsured businesses will finally get properly protected. The market expands, not contracts.

We're building the engine that makes that happen. You'll build the team that builds the engine.

The Role

You'll be Harper's first dedicated recruiting hire—building the talent function from the ground up while closing candidates yourself. This isn't a coordination role. You're sourcing, selling, and closing exceptional people across engineering, sales, and GTM.

You've seen what good recruiting systems look like. You understand the infrastructure needed to scale from 30 to 100+ without creating chaos and debt that someone else has to clean up later. You'll build repeatable processes—sourcing playbooks, structured interviews, calibrated scorecards—while staying hands-on in the pipeline.

Technical recruiting background preferred. You understand tech stacks, know which competitors to pull from, and have a developed mind map of the technical landscape. You can learn GTM recruiting; the reverse is harder.

You'll work directly with the founders. There's no committee. No approval chain. You source it, you sell it, you close it, you own the outcome.

What You'll Do

Close candidates yourself. This is the core. You're in the weeds every day—sourcing, screening, selling, and closing. Engineering roles, GTM roles, whatever the company needs. You know how to find candidates others can't reach and convince them to join before they hit the market.

Build the recruiting infrastructure. Create the systems that let Harper scale without breaking. Repeatable sourcing strategies, structured interview processes, calibrated scorecards, candidate experience that reflects who we are. No chaos, no debt—just a machine that works.

Own technical recruiting. You understand the tech stack and how everything is interconnected. You know which companies to pull from. You can evaluate whether an engineer is actually good, not just credentialed. This is your home base.

Expand into GTM and operations. Once technical recruiting is running, you'll build pipelines for sales, marketing, and ops roles. Your technical foundation makes learning these functions easier—you understand how the pieces fit together.

Partner with founders on hiring strategy. Translate org needs into hiring plans. Push back when job specs don't make sense. Help us figure out what we actually need, not just what we think we want.

Build toward scale. As Harper grows, so does the function. You'll eventually bring on specialized recruiters underneath you. But first, you prove you can do it yourself and build the systems they'll inherit.

You Might Be a Fit If…

You're a closer with a technical background. You've spent years recruiting engineers and technical roles. You understand tech stacks, you know the landscape, you have a mental map of where great people come from. You can evaluate technical talent, not just screen resumes.

You've built systems, not just filled roles. You've seen what good recruiting infrastructure looks like. You know how to create processes that scale—sourcing playbooks, interview loops, offer calibration—without becoming bureaucratic.

You have tenure and depth. You've done 2-3 year in-house stints. You've stayed long enough to see what works, what breaks, and how to fix it.

You move at founder speed. No two-week feedback loops. No committee reviews. If a great candidate is in the pipe, you close them this week. You operate like the roles you're hiring for.

You can sell a trading floor. Harper's culture is intense, loud, collaborative, high-velocity. That filters out a lot of people—and that's the point. You know how to attract candidates who thrive in that environment.

You're ready to own the function. You've maybe managed people, maybe not—but you understand what it takes to build a recruiting org. You want strategic leeway to create the right systems, not just execute someone else's playbook.

Requirements

  • 4-8 years in recruiting, ideally 6-8 years

  • Technical recruiting background strongly preferred

  • Experience building recruiting processes and systems, not just filling roles

  • Ability to source, sell, and close candidates directly—not just coordinate

  • Deep understanding of technical roles, tech stacks, and the engineering talent landscape

  • Based in San Francisco or willing to relocate

Nice to Have

  • Experience at high-growth startups (Series A/B stage)

  • Background recruiting for AI-native or technical sales organizations

  • Experience building employer brand and recruiting content

  • Some people management experience

Compensation

Salary: $125,000 - $185,000 (based on experience)

Equity: Yes

Location: San Francisco, in-office. We build together.

The Process

  1. Founder screen — Initial fit and alignment

  2. People screen — Skills and culture fit

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

To Apply

We're building a vertically integrated AI platform that connects go-to-market, sales operations, customer service, and retention under one architectural roof. That integration creates compounding through feedback loops—every interaction makes the system smarter. Thousands of businesses already trust us.

Most recruiting roles are about filling requisitions. Post the job, screen the resumes, schedule the interviews, hope the hiring manager makes a good call. At Harper, you'll build the talent function from scratch. Your systems will determine the quality of every hire we make. Your closes will shape the company's DNA.

If you've built recruiting infrastructure that scales, if you can close technical talent that others can't reach, if you want to own the function that builds a generational company—send your resume and tell us about the hardest role you ever closed.

We're a championship-minded team. We push each other. We move fast. We care about craft. If that sounds like where you belong, let's talk.

Other jobs at Harper

fulltimeSan Francisco$75K - $125K0.01% - 0.10%1+ years

fulltimeSan Francisco$150K - $200K0.10% - 0.25%1+ years

fulltimeSan Francisco$100K - $140K0.01% - 0.10%1+ years

fulltimeSan Francisco$100K - $140K0.01% - 0.20%Any (new grads ok)

fulltimeSan FranciscoFull stack$140K - $200K0.05% - 0.25%3+ years

fulltimeSan FranciscoRecruiter$125K - $185K0.01% - 0.10%3+ years

fulltimeSan Francisco$80K - $100K0.01% - 0.10%3+ years

fulltimeSan FranciscoFull stack$140K - $200K0.01% - 0.20%3+ years

fulltimeSan FranciscoFull stack$170K - $275K0.10% - 0.50%3+ years

fulltimeUnited States / Remote (US)$40K - $50KAny (new grads ok)

fulltimeSan Francisco$100K - $140K3+ years

fulltimeSan FranciscoFull stack$160K - $230K0.01% - 0.20%3+ years

fulltimeSan Francisco$180K - $220K6+ years

fulltimeSan Francisco$120K - $150K3+ years

fulltimeSan FranciscoFull stack$130K - $190K0.05% - 0.25%3+ years

Hundreds of YC startups are hiring on Work at a Startup.

Sign up to see more ›