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. This is a hands-on leadership role: you'll hire, coach, and grow a small licensed team, own service quality and compliance for the function, and still pick up the phone when it matters.

About the Team:

The Business Insurance team is building Gusto's P&C insurance agency from the ground up, across core small commercial lines including Workers' Compensation. We partner closely with carrier counterparts and work hand-in-hand with product, engineering, design, data, sales, and licensed insurance professionals to ship a quote, bind, and service experience that's fast, accurate, and easy to manage over time. You'll lead the licensed servicing arm of that team — small today, growing fast — reporting into Financial Services leadership.

Here’s what you’ll do day-to-day:

• Hire, onboard, and lead a small team of licensed account managers, setting the service standards, escalation paths, and quality bar they work against.
• Own service-level performance for the book — response and resolution time, endorsement cycle time and accuracy, save rate on the cancellation queue, client satisfaction — and report on it to Financial Services leadership.
• Carry the toughest escalations yourself: contested or rescinded broker-of-record situations, complex coverage disputes, and carrier issues your team can't yet close alone.
• Own the carrier relationship on servicing matters — appointment paperwork, escalation channels, SLA negotiation — and represent the servicing function in cross-functional planning with product and engineering.
• Translate recurring manual work into product requirements, partnering with product and engineering on automation (certificate generation, endorsement submission, intake triage), and push your team's fluency with AI tools in daily service work.
• Own the compliance backbone of the function — supervision documentation, continuing education tracking, and record retention for licensed communications — in partnership with Legal and Compliance.
• Coach your team's growth through regular 1:1s and performance conversations, and build the hiring plan that keeps pace with the book.

Here’s what we'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 compliance instinct sharp enough to carry supervisory responsibility for licensed staff — you know what needs a licensed sign-off, a carrier's approval, or a documented file, and you build that discipline into your team.
• 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.

Preferred: prior experience building or scaling a service function from scratch (agency, insurtech, or MGA); industry designations (CIC, CPCU, CISR, AAI); multi-state or nonresident licensing already in place.

If you don't think you meet every point above but you're excited about this work, apply anyway.

Our cash compensation range for thisrole is $92,245.00-$113,000.00 in Denver. Additional locations will vary based on our geographical pay approach. Final offer amounts are determined by multiple factors, including candidate location, experience, and expertise, and may vary from the amounts listed above.