Business Insurance Servicing Manager

About Gusto

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.

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 this role 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.

At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. 

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Reliable, consistent presence: We expect regular and predictable attendance, whether you're working in-office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. 

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

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