Startups · AI

Customer Service Operations Specialist

Harper · San Francisco · On-site

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About Harper

You make one call, we make the rest. Harper learns your business, works every market that can write it, and brings back the right coverage at the right price. Backed by Peak XV, Y Combinator and Antler.

About 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.

What they're looking for

  • 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
More about this role

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.

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....

Read the full posting on Harper's site ↗

Operations

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