Senior Customer Operations Specialist

At a glance: Atlanta or San Francisco, on site · $85K to $110K in Atlanta, $105K to $130K in San Francisco, plus bonus and equity · Licensed, or licensed within 30 days, paid by us

Harper is an AI-native commercial insurance brokerage, backed by Y Combinator, with offices in San Francisco and Atlanta. We do the insurance work end to end for about 1,000 new small businesses a month, with agents and people working the same accounts.

ROLE IN ONE LINE

Take the cases that are too messy for the standard queue and carry each one all the way to done.

A policy was canceled for nonpayment, the customer says he paid, and the carrier and the finance company disagree. A contractor needs coverage rewritten before a job starts Monday. A certificate request exposes a gap in the policy. These cases do not fit a script.

WHY NOW

About 15% of our service cases are the hard ones, and they take most of the time. The pattern we are fixing: too many hands touch a hard case and nobody takes the next step. This seat is the closer. Our tools put the whole history on one screen, so you start solving instead of digging, and an insurance specialist sits nearby for the judgment calls that need deep expertise.

WHAT YOU OWN

• Cancel and rewrite. Read the full chain of notices, cancellations and reinstatements before telling a customer what is true. Then fix it.
• Complex certificates and endorsements, the ones that need a policy read against a contract.
• Recovery. Deals that stalled, policies that lapsed, coverage that was set up wrong. You bind on the spot when you can.
• The honest conversation. When a customer’s coverage is wrong, you tell them the truth, the options and the deadline, and keep their trust. Refund is not the default.
• The three-times rule. If the same problem happens three times, it becomes a playbook, a check or a product request with the evidence attached.

WHAT DONE MEANS

• Every case has one owner, one current state and one promised update until it is closed.
• Cases that used to bounce between three people close with one.
• The customer knows what happened and why, in plain English.

YOUR FIRST 90 DAYS

• Day 30: you own a lane of hard cases on your own, with evidence on every close.
• Day 60: your cases stop coming back.
• Day 90: the playbook is better because of what you wrote down, and a newer teammate handles one case type you used to.

WHO THRIVES HERE

• You have done detailed, customer-facing work for a few years and moved up quickly.
• You can hold twenty open cases without losing the thread.
• When the records disagree and the customer is angry, you slow down and get it right.
• You use AI tools to find answers faster and can show us how.

WHAT WE TEACH, WHAT YOU BRING

We teach our carriers, finance companies and playbooks, and we pay for your license. You bring persistence, judgment about when to dig and when to escalate, and proof that you learn fast. Insurance experience helps; speed of learning matters more. For now we hire this seat from outside; over time most of these seats go to people promoted from our licensed team.

WHO SHOULD NOT APPLY

• You close cases by transferring them.
• You decide what happened from one status field.
• You need a fixed process to do your best work.

PAY, SCHEDULE AND PLACE

• Atlanta: $85K to $110K. San Francisco: $105K to $130K. Plus bonus and equity. The difference is location; the job is the same.
• In the office Monday to Friday, starting around 8 AM local. These are the cases customers are most upset about, and we stay with them until they are fixed.
• Next steps: insurance specialist for people who go deep on insurance, or Forward Deployed Operator for people who build.

BENEFITS

Health, dental and vision, plus each office’s meals and commuter or parking support. Your license is on us.

HOW WE HIRE (USUALLY INSIDE TWO WEEKS)

1. A call with a founder. We reply within 48 hours at every stage.
2. A work sample: three practice records that disagree about one customer. Find the truth and write what you would tell the customer.
3. A Super Day on site, working practice cases beside the team. We decide within 48 hours.

HOW TO APPLY

Send your resume and tell us about the messiest customer problem you untangled: what was wrong, who you had to move, and how it ended.

Harper is an equal opportunity employer. If you need an accommodation at any point in the process, tell us and we will make it work. For San Francisco roles, we will consider qualified applicants with arrest and conviction records in a manner consistent with the San Francisco Fair Chance Ordinance. Licensed roles require the state’s background check for an insurance license; a record does not automatically rule you out.