Payments Operations Specialist

The role

You will resolve payment problems that could cost a small business its insurance coverage, from a single bounced payment to batch errors affecting hundreds of accounts. You will trace each payment issue to its actual state, talk with customers, and carry problems to documented resolution, while also automating manual reconciliation work.

What you will do

• Trace payment questions to the end: current state, amount, owner and next action, proven from records.
• Match each financed policy to its finance agreement and fix mismatches.
• Work pending cancellations from carrier and finance company portals before the cancellation date.
• Handle disputes and refunds: gather records, coordinate review, inform the customer, record the outcome.
• Reconcile customer, payment and policy records against outside confirmation before closing items.
• Automate manual reconciliation and flag patterns that need product or finance changes.

Required qualifications

• Experience in payment operations, disputes, collections, lending, fraud or accounts receivable, ideally at real volume.
• Ability to write a clear message to an engineer and a calm message to a frustrated business owner.
• Attention to detail: notice when a number is off by one payment and find out why.
• Judgment on when to keep investigating and when to escalate.
• Use of spreadsheets, queries or AI tools to work faster.

Benefits

• Health insurance
• Dental insurance
• Vision insurance
• Meals at each office
• Commuter or parking support at each office
• Bonus
• Equity

Before you apply

• Harper is an equal opportunity employer and offers accommodations during the hiring process on request.
• For San Francisco roles, applicants with arrest and conviction records will be considered in a manner consistent with the San Francisco Fair Chance Ordinance.
• Hiring process: call with customer operations team, then a work sample of three practice records, then an on-site Super Day.

About the company

Harper is an AI-native commercial insurance brokerage backed by Y Combinator, with offices in San Francisco and Atlanta. It handles insurance work end to end for about 1,000 new small businesses a month.