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Salary: USD 110,000 - 150,000 / annual
Harper is an AI-driven commercial insurance platform serving 36 million businesses in America. The company is automating 90%+ of commercial insurance workflows while keeping humans central to complex decisions. Growing ~1,000 customers per month and 100x year-over-year, Harper is building a service organization where expertise, retention, and revenue converge.
As a Customer Service Operations Specialist, you will own the most complex commercial insurance accounts and hardest customer situations. You are the last stop inside service—nothing you pick up gets handed off. You work directly with underwriters and wholesalers on behalf of customers, handling premium audits, inspection recommendations, E&S and surplus lines placements, coverage questions requiring policy expertise, and accounts at risk of cancellation. You guide customers through audits and inspections, manage premium finance arrangements, keep coverage current as businesses grow, and save accounts worth saving by working payment and financing situations.
You own relationships with specific underwriters and wholesalers, building credibility that gets customers better outcomes. You have the latitude to make calls independently; when something needs a founder decision, you bring it with your recommendation. Complex cases get answers in days, not weeks. You also level up the team by turning your expertise into playbooks and training, and you work daily in Harper's service workbench, telling Product and Engineering what to automate so your expertise scales.
This role is for someone who has spent years making hard calls in commercial insurance and is tired of being second-guessed. You thrive on complexity, own cases end-to-end, and want to build a function rather than inherit one. The schedule is Monday–Friday, 8 AM–8 PM ET; the hours are long and the learning curve steep, but the people who thrive here wouldn't have it any other way.
REQUIREMENTS:
- 5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side roles
- Active property & casualty license (company handles non-resident and reciprocal licensing across all 50 states)
- Existing carrier and wholesaler relationships you can activate
- Track record owning complex commercial cases end-to-end, not just triaging
- Comfort with technology; you'll work in the service workbench daily and be expected to identify gaps
- Based in New York City or San Francisco, or willing to relocate; this role is in-office
NICE TO HAVE:
- Surplus lines license
- E&S experience (surplus lines tax, filings, binding packets, DocuSign workflows)
- Premium finance depth (PFAs, reconciliation, finance-company defaults, cancellation reversals)
- Workers' comp and class-code expertise, including NCCI audit disputes
- Wholesaler, MGA, or carrier underwriting-desk background
- Experience at an insurtech or tech-forward brokerage
