Benefit Services Senior Leader - Group Fulfillment

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 hiring a Senior Manager to lead our Group Fulfillment operation within Benefits Services. This is a senior people-leader role — you'll lead a team of managers and the individual contributors who report to them, accountable for delivering benefits accurately and on time for the small businesses who trust Gusto with their team's health coverage. You'll set operational objectives, develop and execute policies, manage capacity planning, and drive outcomes that have a measurable impact on Gusto's customers. You'll lead through your leaders — coaching them to own their teams, hold the bar, and drive change rather than transmit it. You'll also be a senior partner in shaping how AI transforms Fulfillment's work at Gusto. You'll help redesign workflows around it, build an automation roadmap for your team, reduce administrative overhead, and coach your leaders to do the same. About the Team: Group Fulfillment is the team that ensures the promise of benefits becomes reality for new groups and renewing customers. We sit between health insurance carriers and Gusto's customer-facing teams, shepherding new plans, renewals, and carrier switches across the finish line. We measure ourselves by doing it right the first time and on time — because for the customers we serve, "late" or "incorrect" isn't an inconvenience; it's a missed prescription, a delayed procedure, or a stressful call to HR. Customer outcomes are what drive this team. It's where our passion lives, and it's the standard we hold ourselves to every day. As an AI-native company, we don't just use technology — it's the backbone of how we work. Senior leaders on this team are expected to model digital fluency and a proactive approach to leveraging AI tooling to enhance accuracy, speed, and capacity. Every decision you make has a significant daily impact on the lives of the customers we serve. Here’s what you’ll do day-to-day: • Lead 3-5 managers (PEs) and ~40 specialists who report to them, running a structured cadence — weekly 1:1s, team forums, monthly business reviews. • Coach your leaders to operate as drivers, not passengers — owning the rationale behind change, marketing it to their teams, and holding the bar without relitigating decisions. • Develop your leaders through structured calibration, performance reviews, and a clear, evidence-based view of what good looks like at every level on their teams. • Set and own the operational objectives, policies, and work plans for Group Fulfillment, with accountability for headcount and capacity planning across the function. • Deliver against the timeliness, accuracy, and completeness standards that define benefits fulfillment — translating o

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