Customer Success Manager, AI-Native

Harper•San Francisco, CA

1d•$110,000 - $130,000•Onsite

About The Position

Harper is hiring a Customer Success Manager to own a book of small-business customers after they purchase insurance. The manager is the named owner for each account, maintaining customer relationships, identifying changes in the business that could affect coverage, addressing coverage gaps, and coordinating with internal teams. The initial book is about 250 accounts. AI agents review account emails, calls, payments, and documents, flag changes, and draft outreach; the manager determines what matters and contacts customers. The role focuses on retention and relevant account expansion, particularly workers’ compensation, commercial auto, and property coverage. The manager monitors payment issues, pending cancellations, and audits; starts renewal work early with the renewals team; and creates automations to manage the book efficiently. The role does not include remarketing renewals, originating new business from scratch, or processing routine certificates. The position is based in Harper’s San Francisco office, Monday through Friday, with a start time around 7:30–8:00 a.m. It is phone-heavy and involves working directly with busy small-business owners. Harper teaches insurance and pays for the required license, which is expected within 30 days. Compensation is listed as $110,000–$130,000 base and $140,000–$175,000 on-target earnings, or $130,000–$155,000 base and $170,000–$205,000 on-target earnings at the senior level. About one quarter of on-target pay is variable, paid quarterly based on retained premium and bound expansion premium, beginning when the license is issued. Equity is also offered.

Requirements

Experience owning a book of customers at a fintech, software, or services company, with responsibility measured by retention, expansion, or activation.
Use of agents and automation in personal work, with examples of managing a larger book without adding hours.
Directness on the phone and comfort discussing money.
Obtain an insurance license; Harper teaches the insurance material and pays for the license, with the role description expecting licensure within 30 days.

Nice To Haves

Experience serving contractors, truckers, restaurants, or other small-business owners.
Prior insurance experience is not required.

Responsibilities

Own a book of approximately 250 small-business accounts as the named customer contact and close the loop on customer needs.
Monitor account activity and changes in customers’ businesses to identify coverage needs and risks early.
Ensure coverage matches customers’ businesses as they add vehicles, payroll, locations, or contracts.
Identify and pursue relevant coverage expansions, including workers’ compensation, commercial auto, and property, without recommending unneeded coverage.
Address payment problems, pending cancellations, and audits with the appropriate teammates.
Start renewal work early in coordination with the renewals team.
Use AI agents’ account reviews and drafted outreach to determine what requires action and contact customers.
Build automations for repetitive work to manage a larger book without adding hours.
Record reasons when customers leave and identify signs of possible departures before cancellation notices arrive.