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San Francisco, California, United States
Onsite
Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed — on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.
Role in one line: Turn the gap between what a customer bought and what they now need into a clear recommendation and a closed change.
The policy is sold. Then the customer comes back with a certificate of insurance request, or a contract whose insurance requirements look very different from what was originally discussed. That moment is not a service ticket. It is a second commercial conversation, and you own it.
Harper's systems keep the account history, the bound policy, and the new request together. You read the documents, find the gap, lead the customer conversation, and close the right coverage.
Harper's growing policy book creates a commercial moment after the sale. Customers return mid-term with certificate requests and contract requirements that do not match the coverage they bought. That gap needs a dedicated sales motion, not a service queue.
Harper has four Account Executive lanes: New Business, Renewals, Partnerships, and Service. Service is not renewals, and it is not the recovery work inside New Business. It is a smaller team than the other lanes and more brokerage-heavy. You read policies, certificates, and contract insurance requirements, then own the customer decision.
Pick up the account after the sale. Take the customer who comes back with a certificate of insurance request or requirements that differ from what was originally discussed.
Read the source documents. Compare the bound policy, the certificate request, and the contract insurance requirements line by line.
Name the gap. Identify exactly what the requirement asks for that the current coverage does not provide.
Build the coverage plan. Decide with placement and insurance experts how to close the gap credibly.
Lead the customer conversation. Explain the requirement, the current coverage, the options, the price, and the deadline in plain language.
Close the change. Ask for the business, collect the required decision and completion items, and keep ownership through bind.
Protect accuracy. Work within your license and authority. Never let a certificate or a promise overstate what the policy covers.
Record the outcome. Capture what the customer needed, why the gap appeared, and whether they bought, waited, or left.
Accounts that come back with a certificate request or new requirement have a verified comparison against the bound policy and a next customer action.
Recommendations make the current coverage, the requirement, the gap, the option, and the deadline clear.
Bound changes move forward with the accepted option and completion steps recorded.
Accounts that do not buy preserve the customer's stated reason, or an honest unknown when the reason is not available.
Mid-term conversion, retention, and booked revenue improve without selling coverage the requirement does not call for.
You have worked in commercial insurance brokerage or account management and can read a policy, a certificate of insurance, and a contract's insurance requirements.
You can tell a customer who thought they were covered that their requirement asks for more, and keep their trust.
You treat an existing customer's request as the start of a commercial conversation.
You use the policy, the certificate, and the contract instead of relying on one status.
You can earn and maintain the required commercial insurance licenses.
You are based in New York or San Francisco, or ready to relocate.
You want the highest quota and the most variable pay on the sales team.
You treat a certificate request as a service ticket.
You would rather issue a certificate than tell a customer their coverage falls short.
You avoid direct closing conversations.
You need a remote or hybrid default.
Salary: $150,000 to $200,000 OTE, with the mix weighted toward base relative to New Business and Renewals. Top performers earn more.
Equity: Yes.
Location: On-site, New York, Atlanta, or San Francisco. Based here or willing to relocate.
Schedule: Monday to Friday, roughly 8 a.m. to 7 p.m. or 8 p.m., in-office 5 days a week.
Licensing: Commercial insurance producer license required within ~30 days of start; Harper pays for training and licensing.
Harper offers health, dental, and vision insurance. Office-specific benefits are set by working location.
Send your resume and a short post-sale case. Explain the account, what the customer came back with, how the requirement differed from the bound coverage, how you handled the conversation, and the result.
The process has three steps: a 30-minute Zoom to meet the team, about two hours in the office to meet more people, and a super day, after which Harper decides. It moves as fast as you do.
