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.

Once a customer chooses Harper, you’re the reason they stay.

The Thesis

Getting a business insured is only the beginning. After that comes COIs, endorsements, billing questions, renewals, claims—the ongoing reality of being a policyholder. Most brokerages handle this with slow emails and voicemail tag. We handle it with AI and a small, sharp team that actually knows insurance.

Every issue you resolve and every interaction you document teaches our AI what to handle next. You’re not just serving customers—you’re building the system that makes service scale without scaling headcount. The people who learn this operation inside out become the backbone of the company as we grow 20x, 50x, 100x.

The Role

You own post-sale customer service. Business owners call you about their certificates of insurance, policy changes, billing questions, renewal timelines, and claims. You resolve what you can, escalate what you can’t, and make sure nothing falls through the cracks.

You’ll work alongside Sales, the CX team, and our AI systems daily. You need to know enough about commercial insurance to speak confidently with customers—and enough about our tools to move fast. Everything you do feeds back into the product.

What You’ll Do

• Handle customer inquiries all day — COIs, endorsements, billing, renewals, claims coordination; back-to-back, with accuracy and speed

• Own resolution end-to-end — Don’t just take the message; follow up with carriers, track status, close the loop with the customer

• Know the product — Understand policy types, coverage basics, and carrier processes well enough to answer real questions confidently

• Feed the AI system — Your documentation, tagging, and pattern recognition become training data that makes the product smarter

• Flag what’s broken — Surface recurring issues, edge cases, and friction points so they get fixed upstream by Product and Engineering

• Keep customers loyal — Every interaction is a chance to reinforce that Harper is different; professional, fast, and actually helpful

You Might Be a Fit If…

• You’ve worked in customer service, insurance operations, or a similar high-volume support role

• You can explain insurance concepts to a business owner without making their eyes glaze over

• You’re comfortable navigating multiple systems while on a call

• You take ownership of problems—you don’t pass them along and forget about them

• You’re detail-oriented and accurate even when you’re moving fast

• You’re excited about AI tools and want to work at a company building the future of the industry

• You want to grow into CX leadership, operations, or deeper insurance roles as the company scales

Requirements

• Prior experience in customer service, insurance support, or operations roles

• Strong communication skills—clear, professional, and patient

• Ability to multitask: talk, type, and navigate systems simultaneously

• Comfort with technology and willingness to learn new tools quickly

• Based in San Francisco or willing to relocate

Nice to Have

• Insurance industry experience (commercial lines, P&C, brokerage, or carrier-side)

• Bilingual (Spanish)

• CRM or ticketing system experience

• Familiarity with COIs, endorsements, claims processes, or carrier communications

Compensation

• Salary: $80,000 - $100,000 + performance bonuses + equity

• Location: San Francisco, in-office

• Schedule: Monday–Friday, overtime eligible

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

The Process

1. Team lead screen — Skills and culture fit

2. Manager screen — Alignment on pace and expectations

3. On-site day — Meet the team, see the operation, work through real scenarios

To Apply

This is a ground-floor opportunity at one of the fastest-growing companies in insurance. You’ll learn the operation from the inside, work directly with the team building the product, and grow as we scale. If you know insurance, love solving problems for real people, and want to be part of something that’s actually changing the industry—apply.