At a glance: Atlanta (first seat) or San Francisco, on site · $65K to $90K in Atlanta, $85K to $115K in San Francisco, plus bonus and equity · No insurance experience needed · Payments, disputes, lending or reconciliation experience is the skill
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
Resolve the money problems that would otherwise cost a small business its coverage, from one bounced payment to a batch that went wrong for hundreds.
A payment does not reconcile. A customer disputes a charge. A cancellation notice conflicts with the account record. A financed policy has no finance agreement attached. You establish what is actually true, talk to the customer, and carry the issue to a documented resolution.
WHY NOW
Payment problems are the biggest reason small businesses lose coverage with us, and it is rarely because they will not pay. Most do not know they have to, because signing and paying are separate steps. We stood up a payments unit this fall with a simple rule: the queue is at zero every day. This seat makes it a function, alongside an AI operator who automates what you do by hand.
WHAT YOU OWN
- Payment questions, traced to the end. Current state, amount, owner and next action, proven from the records, not from one status field.
- Finance agreements. Match each financed policy to its agreement and fix the ones that do not match. A policy marked paid in full that was actually financed is the error that multiplies.
- Pending cancellations. Work the list from the carrier and finance company portals before the cancellation date, not after. The portal’s list is the truth, not our sheet.
- Disputes and refunds. Gather the records, coordinate the review, tell the customer, and record the outcome. Refunds go through one channel, every time.
- Reconciliation. Compare the customer, payment and policy records with outside confirmation before you close anything.
- The fix behind the fix. Automate the reconciliation you did by hand last month, and flag the patterns that need a product or finance change.
WHAT DONE MEANS
- Every conclusion names its evidence and the account or transaction it belongs to.
- Cancellation answers reflect the latest event in the chain, not the loudest notice.
- Repeat contacts go down because the issue was fixed and explained.
YOUR FIRST 90 DAYS
- Day 30: you work the pending-cancellation list on your own and close cases with the evidence attached.
- Day 60: you own one recurring money problem end to end, with a weekly number.
- Day 90: you have automated or eliminated at least one manual reconciliation step.
WHO THRIVES HERE
- You have worked in payment operations, disputes, collections, lending, fraud or accounts receivable, ideally somewhere with real volume.
- You can write a crisp message to an engineer and a calm one to a frustrated business owner in the same hour.
- You notice when a number is off by one payment, and you find out why.
- You know when to keep digging and when to escalate.
- You use spreadsheets, queries or AI tools to work faster, and you can show us what you built.
WHAT WE TEACH, WHAT YOU BRING
We teach premium finance, our carriers’ billing, and how a policy cancels and reinstates. You bring payments judgment, numeracy and calm on the phone with someone worried about losing their coverage.
WHO SHOULD NOT APPLY
- You want a back-office job with no customer conversations.
- You close cases when you transfer them.
- You decide payment or cancellation status from one field.
PAY, SCHEDULE AND PLACE
- Atlanta: $65K to $90K. San Francisco: $85K to $115K. Plus bonus and equity. The difference is location; the job is the same.
- In the office Monday to Friday, starting around 8 AM local. Weekly carrier sweeps, cancellation dates and finance-company cutoffs set the rhythm, and some weeks the list is long.
- Next steps: senior payments roles, team lead, or the team that automates payments.
BENEFITS
Health, dental and vision, plus each office’s meals and commuter or parking support.
HOW WE HIRE (USUALLY INSIDE TWO WEEKS)
- A call with our customer operations team. We reply within 48 hours at every stage.
- A work sample: three practice records that disagree about one customer’s payment. Find the truth and draft the message to the customer.
- A Super Day on site, working practice cases beside the team. We decide within 48 hours.
HOW TO APPLY
Send your resume and a short example of a money problem that crossed several systems or teams: how you found the real state, what you told the customer, and how you proved it was resolved.
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.
