Customer Success Manager, AI-Native

At a glance: San Francisco, on site, five days · $110K to $130K base, $140K to $175K on-target; senior $130K to $155K base, $170K to $205K on-target · Plus equity · License within 30 days, paid by us · No insurance background needed

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

Own a book of small businesses after they buy, keep them covered as they grow, and run the whole book with agents.

A small business buys a policy and keeps moving. It hires its first employee, adds a truck, wins a contract that requires workers’ comp, opens a second location. Those are triggers, and they are predictable. At most brokerages nobody notices until the renewal, or the claim. At Harper you notice first.

Why now

Our most important accounts need one named owner, and today too many people touch them. Hundreds of our customers also need coverage they do not have yet, most often workers’ comp and commercial auto, and that is the cheapest growth we have. You start with about 250 accounts. Agents read every email, call, payment and document on each one, flag what changed, and draft the outreach. You decide what matters and make the call.

What you own

- One named owner per account, and it is you. The customer knows who to call, and you close the loop.
- Coverage that matches the business. New vehicles, payroll, locations and contracts. Catch the gap before it becomes a problem.
- Growth where it is real. Workers’ comp, commercial auto and property for businesses that need them. Never coverage they do not need.
- Accounts protected early. Payment problems, pending cancellations and audits: you see them first and get them fixed with the right teammate.
- Renewals started early, with our renewals team, well before the deadline.
- Your own automations. The parts of the book that eat your week, you automate.

What done means

- No surprise cancellations in your book.
- When a customer is thinking about leaving, you see it in the account before the notice arrives; when one leaves, the reason is on the record.
- Your book is bigger than when you started, and you did not add hours to run it.

Your first 90 days

- Day 30: you know your book, you are licensed or close, and every account has a current status and a next action.
- Day 60: you have automated what was eating your week, and your first expansions have closed.
- Day 90: no surprise cancellations, and the book has grown.

Who thrives here

- You have owned a book of customers at a fintech, software or services company, with a number: retention, expansion or activation.
- You use agents and automation in your own work and can show how you handled a bigger book without more hours.
- You are direct on the phone and comfortable talking about money.
- Bonus: you have served contractors, truckers, restaurants or other small business owners.

What we teach, what you bring

We teach the insurance and pay for your license. You bring book ownership, curiosity about what changed in a customer’s business, and the habit of building tools for yourself.

Who should not apply

- You want the highest quota and the most variable pay. Our renewals and new business teams carry more.
- You treat a request for a certificate as a ticket rather than a conversation.
- You want to run quarterly business reviews for ten strategic accounts. This is a book of hundreds.

Pay, schedule and place

- $110K to $130K base and $140K to $175K on-target, or $130K to $155K base and $170K to $205K on-target at the senior level. About a quarter of on-target pay is variable, paid quarterly on retained premium and bound expansion premium, starting when your license is issued. Plus equity.
- In the San Francisco office Monday to Friday, starting around 7:30 to 8 AM. Phone-heavy: small business owners are busy and direct, and they expect you to be the same.
- You do not remarket renewals or sell new business from scratch, and you do not process routine certificates. Those teams close; you bring them in and stay on the account.

Benefits

Health, dental and vision. Breakfast, lunch and dinner at the office, commuter benefits and a gym membership. Your license is on us.

How we hire (usually inside two weeks)

- A 15-minute call with a founder. We reply within 48 hours at every stage.
- A book sample: a synthetic book of 40 accounts. Find the real expansion opportunities and the accounts at risk, write the outreach for two, and take one hard call with us.
- 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 a customer you kept or grew: what you noticed first, how you noticed it, and what you built to notice it sooner next time.

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. 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.

Compensation

Base Salary $110K – $130K • Offers Equity