Customer Service Representative

Harper•San Francisco, CA

19h•$22 - $26•Onsite

About The Position

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.

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 Haves

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

Responsibilities

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