Backed by General Catalyst, Kleiner Perkins and Y Combinator.
About the role
Gusto is building its own P&C insurance agency, and our servicing team is growing right alongside it. You'll lead the licensed team that keeps our commercial book correctly covered — endorsements, renewals, claims, carrier relationships — while building the systems, SOPs, and automation that let that team scale without headcount scaling at the same rate. Found on 1752vc Careers, the job board for startup and VC roles.
What they're looking for
- 5+ years of commercial lines service experience at an independent agency, brokerage, or carrier, including 1–2+ years leading or supervising a service team
- Workers' Compensation depth — class codes, experience modifiers, premium audits, pay-as-you-go WC experience is a strong plus — and the ability to turn that depth into training and SOPs for a team
- Experience working in carrier portals (Hartford, AmTrust, etc) and comfort partnering directly carrier relationship managers
- AI and automation fluency — you've used AI tools in real service work, can coach a team to use them well, and have a track record of turning manual processes into automated ones
- A coaching-first leadership style: you'd rather build a team that outgrows the need for you on any single case than be the best individual servicer in the room
- An active Property & Casualty producer license (Colorado resident preferred, or obtainable within 90 days with Gusto's support), plus willingness to obtain nonresident licenses across our operating footprint
More about this role
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.
All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy .
AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.
Gusto is building its own P&C insurance agency, and our servicing team is growing right alongside it. You'll lead the licensed team that keeps our commercial book correctly covered — endorsements, renewals, claims, carrier relationships — while building the systems, SOPs, and automation that...
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