Customer Operations Specialist, Payments
Description
Customer Operations Specialist, Payments
Role in one line: Resolve the customer problems that cross payments, disputes, cancellations, audits, and insurance operations before they become repeat calls or unresolved risk.
A payment does not reconcile. A customer raises a dispute. A cancellation notice conflicts with the account record. An audit creates a question nobody can answer from one screen. You establish the real state, speak with the customer, and carry the issue to a documented resolution.
Harper's systems can surface records and prepare routine service work. This role handles the customer problems that still require judgment, persistence, and direct communication across payments and insurance operations.
Why now
Harper serves a growing base of small businesses across many carriers, payment paths, and policy workflows. Routine requests belong with Customer Service. This specialist owns the harder cases that cross systems or require reconciliation across finance, insurance, and service records.
You own payments and disputes, plus the related cancellations, audits, insurance questions, phone work, and complex service problems that often arrive with them. The job is broad because the customer's problem rarely respects one system boundary.
What you own
Resolve payment questions. Trace the payment question through the available records and identify the current state, amount, owner, and next action.
Work disputes end to end. Establish the issue, gather the source records, explain the current state, coordinate the required review, and record the final outcome.
Handle cancellation complexity. Read the full event chain, including notices, effective cancellations, reinstatements, and rescissions, before telling a customer what is true.
Support audits. Help customers understand the audit request, identify the records needed, and route licensed or specialized questions to the correct owner.
Answer general insurance questions within authority. Explain process and recorded facts clearly. Escalate coverage advice and licensed decisions rather than guessing.
Talk to people. Use the phone when a live conversation will resolve confusion faster than another automated message.
Reconcile across systems. Compare the customer record, payment record, policy record, communications, and external confirmation before closing a case.
Own the next action. Keep one named owner, one current state, and one promised update point until the issue is complete.
Find the repeated cause. Flag patterns that should become a permanent product, process, training, or finance fix.
What resolved means
Cases preserve the customer's question, the amount or policy involved, the records checked, the owner, and the next action.
Payment conclusions name the evidence and the account or transaction they belong to.
Disputes end with a recorded resolution, customer notification, and any required financial or policy correction.
Cancellation answers reflect the latest event in the chain, not the loudest notice.
Repeat contacts decline because the underlying issue was resolved and explained clearly.
Who thrives here
You have worked in payments, disputes, cancellations, audits, insurance service, or another high-volume problem-solving environment.
You can read several systems without losing the customer's question.
You are calm and direct with people who are frustrated or confused.
You document facts carefully and distinguish a missing record from a missing real-world action.
You know when to keep investigating and when to escalate.
You are comfortable with phone work throughout the day.
You are based in Atlanta or San Francisco, or ready to relocate to one of those offices.
Who should not apply
You want a back-office role with no customer conversations.
You close cases when you transfer them.
You infer payment, cancellation, or coverage from one status field.
You avoid difficult conversations or detailed reconciliation.
You need a remote or hybrid default.
Benefits
Harper offers health, dental, and vision insurance. Office-specific benefits will be set by working location.
How to apply
Send your resume and a short example of a customer problem that crossed several systems or teams. Explain how you established the real state, what you told the customer, and how you proved the issue was resolved.
As published by ashby · 7 questions · 4 written answers
Basics
Name, Email, Resume
Short answers (1)
- LinkedIn URL
Pick from a list (2)
- Harper is on-site, full-time, in our San Francisco office, and the sales floor runs long, high-intensity days (our AEs are on roughly a 5am–7pm schedule, Mon–Fri). You'll also need to obtain an insurance producer license within ~30 days of starting (we pay for the training and exam). Can you do all of this? (Yes / No)
- Are you legally authorized to work in the United States optional
Written answers (4)
- Why Harper? What attracted you to this role?
- Almost nobody comes to Harper for insurance — what pulls people here is the mission and the AI-native rebuild of a broken, human-led industry, done at startup intensity. In 2–3 sentences: what specifically about Harper's bet (not "AI" or "startups" in general) makes you want to carry a revenue number here, and why phone-first, in-the-trenches selling over a strategy, partnerships, or back-office seat?
- Tell us about the best stretch of selling you personally did — your highest-volume or highest-conversion period. Give the real numbers (dials or live conversations per day, your quota attainment or close rate, where you ranked on the team) and name the single hardest part you had to push through. (2–3 sentences. Tell us what you did, not what your team did.)
- This is 100+ calls a day to small-business owners — transactional, short-cycle, high-velocity, not enterprise cycles, decks, or partnerships — and the "build the system / write the playbook" part happens on top of a full close sheet, not instead of it. What's your honest reaction to that day, and what was your most recent quota attainment (the actual %) at that kind of volume?
Y Combinator