Customer Success Manager, AI-Native

The role

You will own a book of about 250 small business accounts after they buy a policy. You will keep their coverage current as the business grows, and you will run the book with AI agents.

What you will do

• Own a named book of small business accounts after they buy.
• Track changes in each customer's business, such as new vehicles, payroll, locations and contracts, and close coverage gaps.
• Grow coverage where it is needed, such as workers' comp, commercial auto and property.
• Catch payment problems, pending cancellations and audits early and get them fixed.
• Start renewals early with the renewals team.
• Use agents to read account activity, flag changes and draft outreach.
• Automate the parts of the book that take up your week.

Required qualifications

• Experience owning a book of customers at a fintech, software or services company, with a measured result such as retention, expansion or activation.
• Experience using agents and automation in your own work, and showing how you handled a bigger book without more hours.
• Direct phone communication and comfort talking about money.
• Insurance license, obtained after hiring; Harper pays for it.

Nice to have

• Experience serving contractors, truckers, restaurants or other small business owners.

Benefits

• Health, dental and vision insurance.
• Breakfast, lunch and dinner at the office.
• Commuter benefits.
• Gym membership.
• Insurance license paid by the company.
• Equity.

Before you apply

• Harper will pay for the insurance license, which must be obtained within 30 days.
• Licensed roles require the state's background check for an insurance license; a record does not automatically rule you out.
• The hiring process includes a 15-minute call, a book sample of 40 synthetic accounts, and an on-site Super Day, usually within two weeks.

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, with agents and people working the same accounts.