Full posting
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 — moving from a third-party referral model to a first-party, payroll-integrated experience that protects small businesses as they grow. We have policies in force and a growing book of business. What we don't yet have is a licensed account manager inside the company servicing it. You'll be our first, and the foundation of the service function: owning daily servicing of the book, running the proactive outreach that keeps clients correctly covered, and turning every recurring case into a product spec so the next hundred don't need a human.
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. The team is small, cross-functional, and highly execution-oriented — ideal for someone who thrives in ambiguity and wants to build durable operations in a zero-to-one environment.
Here’s what you’ll do day-to-day:
- Own daily servicing of the assigned book: endorsements, certificates of insurance, coverage questions, premium audits, billing disputes, cancellations, reinstatements, and renewals.
- Accountable for outcomes connected to Business Insurance customers.
- Serve as the liaison between insureds, carriers, and our licensed producers — explaining coverage, exclusions, and exposures in plain language.
- Run proactive outreach using payroll data a traditional agency doesn't have: catching FEIN mismatches, new-state hires, and class code drift before they become coverage gaps.
- Work the pending cancellation and non-pay queue — find out what's actually driving each cancellation, fix what's fixable, and secure reinstatement or replacement coverage.
- Handle claims intake and status reporting, and coordinate hand-offs to the carrier's adjusting team.
- Document every recurring case as a product spec, partnering with product and engineering to automate certificate generation, endorsement submission, and intake triage — using AI tools daily for drafting, summarization, and triage.
- Write the SOPs, escalation paths, and service standards for the team
Here’s what we're looking for:
- 5+ years of commercial lines service experience at an independent agency, brokerage, or carrier, servicing small commercial accounts end to end.
- Workers' Compensation depth — class codes, experience modifiers, premium audits, and state-specific requirements. Pay-as-you-go WC experience is a strong plus.
- Experience working in carrier portals (Hartford, AmTrust, etc) and coordinating with carrier underwriting/servicing teams to service an agency book of business.
- AI and automation fluency — you've used AI tools in real service work (drafting, summarization, triage, outreach) and have opinions about where they hold up and where they don't.
- Evidence you build, not just execute — a process you documented, a workflow you redesigned, or a tool you got built. We'll ask for specifics.
- A compliance instinct: you know when something needs a licensed person, a carrier's sign-off, or a documented file, and you don't improvise around it.
- An active Property & Casualty producer license (Colorado resident preferred), or willingness to obtain one within 90 days of starting — we sponsor the coursework and exams — plus willingness to obtain nonresident licenses across our footprint over time.
Preferred: industry designations (CISR, CIC, AAI, ACSR, or CPCU); multi-state or nonresident licensing already in place; experience at a digital agency, insurtech, or MGA, or having stood up a service function from scratch.
If you don't think you meet every point above but you're excited about this work, apply anyway.
Our cash compensation amount for this role is between $83,265 - $102,000/year in Denver. 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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