AI Customer Service Operator

The Mission

Harper is building the first AI-native commercial insurance brokerage. We're not just trying to make humans 10x better—we are shifting the atomic unit of work from human judgement to systems. We believe this will remove inefficiencies, helping businesses around the country that need coverage and carriers who provide it.

Venture-backed by Y Combinator, our founding team brings experience from Coatue, Carlyle, Goldman Sachs, Tesla, Alloy, and Boston Consulting Group. We've achieved $5M in ARR in under a year, with over 3,000 active clients and 200+ new accounts every single day. We're building the team that will service over 10,000+ new customers per month by the end of next year.

To do this, we need to engage ~50,000 businesses monthly, and every one of those conversations is training data for the AI systems that will transform a $100B+ industry.

This role is the operational engine of that transformation—delivering for the customers who are our why.

Why This Role Exists

Most commercial insurance customer service operates like it's 1999 - reactive, manual, and disconnected. Commercial insurance service at a retail agency is complex: policy endorsements, coverage analysis, certificate management, claims coordination, carrier negotiations, compliance documentation, and relationship management. There's no way to scale to 10,000+ customers monthly without doing this work manually first, then templatizing it, then automating it, then scaling it massively—all while maintaining compliance and consistency.

You are the analyst who documents, templates, and designs the systems that will automate customer operations. You're not processing requests—you're building knowledge bases, designing workflows, and creating the automation infrastructure that will replace manual work.

You're the human in the loop who ultimately automates your way out of this job. That's not a threat, it's the point.

What You'll Do

• Document customer service interactions, edge cases, and decision points to build knowledge bases and inform system design

• Create service templates and workflows while determining what can be standardized vs. requires human judgment

• Analyze cross-channel service patterns to identify automation opportunities and advise on system architecture improvements

• Advise product, engineering, and operations teams on strategies to scale from current volume to 10,000+ customers monthly

• Develop operational procedures, training protocols, and quality assurance frameworks; test and validate automated workflows

• Conduct customer service interactions across channels (phone, email, chat) for research, testing, validation, and intelligence gathering

What We're Looking For

• Recent graduates who want to build something from zero

• Fascination with how businesses work

• High tolerance for repetitive work when it's in service of something bigger

• Autonomy—you figure shit out without needing hand-holding

• Pattern recognition—you spot trends others miss

• Grit—delayed gratification is your superpower

• Pace

• Taste

• Meaning

Required:

• Obsessive attention to detail

• Incredible organization

• Proficiency with technology and AI tools

• Clear communication under pressure

• Willingness to grind when the work is unglamorous

Preferred:

• Experience at a technology company in a highly regulated industry (does not have to be insurance)

The Culture:

We're building a team that works hard and wins together.

• In-office in SF: Trading floor energy, NOT SF WeWork vibes

• Group lunches and dinners: We eat together at 6:30pm most nights

• Intense but fun: The hours are long, but you're doing it with people you actually like and building something that matters

• Meritocracy: Excel here → fast track to leadership roles.

The Progression: This is a 6-18 month intense marathon sprint that launches you into AI Operations Leadership, Product Management, Strategic Operations, or Business Intelligence roles.

Think less "insurance company" and more "elite team on a mission to transform a massive unsexy industry using AI."