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.

You're the underwriting lens that makes sure everything we build actually holds up in the real world.

The Thesis

You'll pull up real submissions and AI outputs on day one. You'll review what our system generated, compare it to what a carrier underwriter would actually expect, and tell us—directly—what's wrong. You've done this your entire career. The difference here is that your judgment doesn't get applied to 50 deals. It gets scaled across thousands.

Harper has its own operating system and AI infrastructure. We're not looking for someone to recommend vendor tools or bring in external processes. We need someone who's lived the carrier side—who knows what makes a submission stand out vs. get kicked back—and wants to shape our systems from the inside. You're not the AI. You're the person who makes sure the AI thinks like an underwriter.

The Role

You won't manage a book of business, bind policies, or own carrier relationships. But this isn't less work than a traditional underwriting seat—it's different work, and it's harder. Your focus is on product and process—making sure our systems work the way the industry actually works, every day, in the details.

You'll sit next to engineers and shape how our AI thinks about risk. You're a thought partner, not a requestor who submits feedback and waits. When something's wrong with a submission workflow, you don't write a memo—you walk over and fix it together. There is no established underwriting review function waiting for you. No QA team, no structured review process. You're building this while doing the work.

This is a small team, high-intensity environment. The CEO is in the details on submissions, quoting speed, and carrier relationships. Everyone operates well beyond their job description. If that sounds like where you do your best work, keep reading.

What You'll Do

• Review real submissions and AI outputs daily — Pull up what our system generated, compare it to what a carrier underwriter would expect, and tell us what's broken; this is your core loop, not a periodic review

• Build the underwriting review function from scratch — There's no established QA process for submission quality; you define what good looks like, create the review cadence, and own the standard

• Gate what ships — Review risk assessment logic, submission workflows, and quoting outputs before they reach customers; nothing with underwriting implications goes live without your sign-off

• Shape how our AI thinks about risk — Work directly with engineers to translate underwriting judgment into system logic; you're a thought partner sitting next to the team, not a requestor sending requirements over email

• Give us carrier-side feedback — Tell us what carriers and wholesale partners actually care about; what frustrates them about working with brokerages; help us build processes that make their lives easier

• Flag what we're missing — Coverage gaps, compliance issues, edge cases, and submission quality problems that a carrier-side underwriter would catch immediately but our team might miss

You Might Be a Fit If...

• Your instinct is to pull up the actual submissions before reading any strategy docs

• You've spent 7+ years in commercial P&C underwriting and you know the submission-to-bind lifecycle cold

• You'd rather shape an internal AI system than recommend buying a vendor solution

• You're comfortable giving direct, unfiltered feedback and poking holes in how things work

• You want to sit next to engineers and shape the product, not send feedback memos from across the office

• You can explain underwriting concepts clearly to people who aren't underwriters—and you enjoy it

• You want to work at the pace of a company adding ~1,000 customers a month, not a carrier review cycle

Requirements

• 7+ years of commercial P&C underwriting experience

• Deep working knowledge of commercial lines products—GL, BOP, WC, commercial property, professional liability, and/or cyber

• Experience evaluating submissions, assessing risk, and working with brokers or agents on the carrier side

• Able to be a thought partner with engineers—not just translating underwriting concepts, but thinking through how to encode them into systems

• Comfortable building without an established underwriting review team or QA infrastructure—you're creating this function, not stepping into one

• Comfortable in a high-intensity, in-office, fast-paced environment with fixed working hours

• Based in San Francisco or willing to relocate

Nice to Have

• Insurance designations (CPCU, AU, AINS, CIC, ARM)

• Experience at an MGA, program administrator, or wholesaler

• Familiarity with how AI/ML is being applied in insurance

• Surplus lines or non-admitted market experience

• Prior startup or high-growth company experience

Compensation

• Salary: $150,000–$190,000 + performance bonuses & equity

• Location: San Francisco, in-office

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

You've seen firsthand how brokerages submit to carriers—and everything that goes wrong along the way. If you want your underwriting judgment to shape how an AI-first brokerage builds its systems, not just review individual deals—send your resume and a few lines on what's broken about how brokerages submit to carriers today and what you'd fix first.

Compensation Range: $150K - $190K