Customer Service Representative

The Problem

36 million businesses in America need insurance—it's not optional.
77% are underinsured. 40% have no coverage  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.

Small business owners are used to their insurance broker never calling back. You're the reason ours do.

Insurance is the one bill a small business owner can't afford to get wrong, and most brokers make them work for it—voicemail, dead ends, a week of silence. Being the opposite of that is a real competitive advantage, and it's the entire point of this team. When someone calls Harper, they reach a person who finds their account, tells them exactly what's happening next, and then makes it happen.

That doesn't come from software. It comes from people who genuinely enjoy this kind of work: fast on the phone, dozens of open threads held in their head, and real satisfaction in taking a full list down to zero. It's a craft, and the people who are great at it become the customer's favorite part of doing business with us. There are real paths from this seat into service, sales, and operations.

You're on the phone with business owners all day—inbound and outbound—from our office in downtown San Francisco. Two shifts cover the day: an early one for East Coast customers and a later one through the West Coast close. You'll be assigned to one based on business need.

Inbound, you're the first person a customer talks to. You pull up the account, work out what they actually need, and tell them exactly when they'll hear back. Outbound, the list is yours: payments, documents, renewals, and the follow-ups that keep somebody's coverage from lapsing. The volume is real—back-to-back calls and long lists—and the people who love this job love that part.

You don't need an insurance background to start. We'll teach you the systems, the playbooks, and the vocabulary. What we're hiring for is judgment on the phone: hearing the difference between confused and genuinely upset, catching the thing the customer didn't say, and knowing exactly who to pull in when a problem is bigger than the call. Quoting and coverage advice belong to a licensed seller, so you'll never be asked to advise on a policy—everything else, you carry as far as it goes.

• Pick up and take it personally — You're the first human a business owner reaches; find their account fast, get to the real ask, and tell them precisely when they'll hear back

• Keep every promise you make — A callback time is a commitment; no customer should ever have to chase Harper to find out what happened

• Take the list to zero — Payments, documents, at-risk cancellations, renewals; an empty list at the end of your shift is the whole game

• Chase it like it's yours — Three attempts across three days on a standard follow-up, up to seven touches on a payment issue by phone, text, and email; you stop when it's solved, not when it's hard

• Own the whole answer — Track down the document, the payment link, or the one person who can unblock it; nothing gets closed just because it got called

• Leave a clean trail — Log what happened and what's still open, so the next teammate picks up mid-story and the customer never repeats themselves

• Get the right specialist in fast — Financing, coverage, and genuinely complex problems have owners; pulling them in quickly is part…