Customer Service Operations Specialist

The Problem36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing.Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step.We're adding ~1,000 customers per month. We've grown 100x since last year. We're looking to do even more this year—and that's why we're hiring.The accounts that need an expert instead of a script—those are yours.The ThesisCommercial insurance gets complicated fast. A business opens a second location, wins a contract with insurance requirements it doesn't currently meet, adds a fleet, gets hit with a premium audit, grows out of the market it started in, or needs coverage that doesn't exist on a standard form. Those accounts don't need a queue. They need somebody with deep expertise and the latitude to act on it.That's this team. You take the accounts that call for real judgment, you work them directly with the underwriters and wholesalers, and you stay on them until the customer has an answer. Then your expertise becomes the playbook the rest of the service organization runs on, which is how a small team serves a book growing this fast.We're also building this tier now rather than handing you someone else's version of it. Harper's long-term plan puts service at the center of the company—expertise, retention and revenue all living in one organization—and the specialists we hire first will shape what that looks like.The RoleYou own our most complex accounts and the hardest customer situations. Premium audits and inspection recommendations that carry real deadlines. Renewals worth remarketing to get a business better terms. E&S and surplus lines placements, with the filings and binding packets that come with them. Premium finance arrangements and the paperwork behind them.Coverage questions that need someone who can read a policy form and a contract and explain what's actually covered. And the accounts at risk of cancellation, where somebody's coverage is genuinely on the line and a customer needs a person who will solve it.You own relationships too. Every underwriter and wholesaler we work with has a named owner on this team, and you'll be one of them. You're the person they pick up the phone for—and the person who can get a real answer for a customer because you've built that credibility over years.You're the last stop inside service, which means nothing you pick up gets handed to somebody else to figure out. You have the latitude to make the call, and when something genuinely needs a founder's decision you bring it to them with your recommendation attached. Complex cases get answers in days here, not weeks.What You'll DoOwn the complex accounts end to end — The situations that need experience rather than a script; you keep them until the customer has a real answerWork the markets on your customers' behalf — Partner with underwriters and wholesalers to place hard risks, remarket renewals for better terms, and find a home for businesses standard markets won't writeGuide customers through audits and inspections — Premium audits, payroll and sales verification, inspection recommendations with deadlines; make sure the final number and the required changes are right and understoodHandle E&S and surplus lines work — Eligibility, filings, surplus lines tax, binding packets, and the documentation that has to be correct the first timeMake coverage match the business — Businesses change constantly: new locations, vehicles, payroll, equipment, and contracts with new requirements; keep coverage, class codes and records current as they growSave accounts worth saving — Work payment, financing and cancellation situations with the customer and the finance company so coverage stays in forceBe the name your carriers know — Own specific underwriter and wholesaler relationships and build the kind of credibility that gets customers a better outcomeLevel up the team around you — Turn what you know into playbooks, train the service team, and grow the tier-two group into people who can handle more every monthMake the system smarter — Work in our service workbench daily and tell Product and Engineering what to automate, so your expertise scales past your own calendarYou Might Be a Fit If...You're the person colleagues bring the case nobody else can crackYou have real relationships with underwriters and wholesalers—and they take your callYou'd rather decide with the facts you have and document your reasoning than let an account sit for three weeksYou're tired of needing three approvals to do the obviously right thingYou can hold a case open for days without losing the thread, and keep twenty of them straightYou're curious about AI tools and want to tell engineers what to build, not wait for permissionYou want to build this function, not inherit someone else's version of itYou know startup pace is a real adjustment from a traditional brokerage and you want it anywayRequirements5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side rolesActive property & casualty license—we handle non-resident and reciprocal licensing across all 50 statesExisting carrier and wholesaler relationships you can put to workA track record owning complex commercial cases end to end, not just triaging themComfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls shortBased in New York City or San Francisco, or willing to relocate; this role is in-officeNice to HaveSurplus lines licenseE&S experience: surplus lines tax, filings, binding packets, DocuSign workflowsPremium finance depth: PFAs, reconciliation, finance-company defaults and cancellation reversalsWorkers' comp and class-code expertise, including NCCI audit disputesWholesaler, MGA or carrier underwriting-desk backgroundExperience at an insurtech or tech-forward brokerageCompensationSalary: $110,000–$150,000 + performance bonuses + equityLocation: San Francisco, Atlanta, or New York City, in-officeSchedule: Monday–Friday, 8 AM – 8 PM ET. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.Start date: ImmediateBenefitsHealth, dental, and vision insuranceCommuter benefitsTeam meals and snacksThe ProcessPeople screen — Initial fit and alignmentFounder screen — Insurance judgment, operating instinct, and culture fitSuper day — Work through real cases with the team and see how you operateTo ApplyIf you've spent years making the hard calls and watching them get second-guessed by people who couldn't make them, this is the seat where the decision is yours. Send your resume and tell us about the messiest commercial account you ever untangled—what was wrong, who you had to move, and how it ended.