Customer Service Operations Specialist

THE PROBLEM

36 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 THESIS

Commercial 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 ROLE

You 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 DO

• Own the complex accounts end to end — The situations that need experience rather than a script; you keep them until the customer has a real answer
• Work 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 write
• Guide 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 understood
• Handle E&S and surplus lines work — Eligibility, filings, surplus lines tax, binding packets, and the documentation that has to be correct the first time
• Make 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 grow
• Save accounts worth saving — Work payment, financing and cancellation situations with the customer and the finance company so coverage stays in force
• Be the name your carriers know — Own specific underwriter and wholesaler relationships and build the kind of credibility that gets customers a better outcome
• Level 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 month
• Make the system smarter — Work in our service workbench daily and tell Product and Engineering what to automate, so your expertise scales past your own calendar

YOU MIGHT BE A FIT IF...

• You're the person colleagues bring the case nobody else can crack
• You have real relationships with underwriters and wholesalers—and they take your call
• You'd rather decide with the facts you have and document your reasoning than let an account sit for three weeks
• You're tired of needing three approvals to do the obviously right thing
• You can hold a case open for days without losing the thread, and keep twenty of them straight
• You're curious about AI tools and want to tell engineers what to build, not wait for permission
• You want to build this function, not inherit someone else's version of it
• You know startup pace is a real adjustment from a traditional brokerage and you want it anyway

REQUIREMENTS

• 5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side roles
• Active property & casualty license—we handle non-resident and reciprocal licensing across all 50 states
• Existing carrier and wholesaler relationships you can put to work
• A track record owning complex commercial cases end to end, not just triaging them
• Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short
• 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 and 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

COMPENSATION

• Salary: $110,000–$150,000 + performance bonuses + equity
• Location: San Francisco, Atlanta, or New York City, in-office
• Schedule: 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: Immediate

BENEFITS

• Health, dental, and vision insurance
• Commuter benefits
• Team meals and snacks

THE PROCESS

1. People screen — Initial fit and alignment
2. Founder screen — Insurance judgment, operating instinct, and culture fit
3. Super day — Work through real cases with the team and see how you operate

TO APPLY

If 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.