Benefit Services Senior Leader - Group Fulfillment

Gusto, Inc.•Chicago, IL

4h•$119,185 - $154,940•Hybrid

About The Position

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. 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.

Requirements

5+ years of leadership experience, including 2 years leading other leaders (preferred).
Demonstrated track record of setting operational strategy, owning a budget, and being accountable for business-segment impact.
Experience driving meaningful org change — restructures, role evolution, process redesign, or scaling — and bringing teams along through it.
A driver mindset: You own the rationale behind change and market the why, not just relay the what. You make decisions decisively within your authority, communicate them once, and don't relitigate them when they meet pushback.
You bring proposals with data-backed reasoning rather than reacting to incoming requests, and you name hard things directly — in the room they belong in, with the people who need to hear them.
Operational rigor: Comfortable reading dashboards, interrogating data, and finding the gap before it shows up as an escalation.
Track record of operating against time-sensitive SLAs in a benefits, healthcare, payroll, banking, insurance, or comparable regulated operations environment.
You manage costs and capacity as a leader — you know what your function spends, why, and where the leverage is.
AI fluency at the leader level: You actively use AI to redesign how leadership tasks get done. You've personally redesigned or automated a workflow, built an agent, prototyped a tool, or stood up an automated process that meaningfully changed how a team operates. At a minimum, you operate with AI integrated into your daily workflow with a clear trajectory toward building and deploying new applications.
You coach AI fluency in others and evaluate new tools with judgment. You can teach your team how to use AI to do their job differently, hold them accountable for adopting it, and tell the difference between a demo that's impressive and a tool that will actually move the needle in your operation.
Coaching and development depth: You develop leaders through structured coaching, not directives. Team members leave your 1:1s with a clearer picture of the bar, not just of your opinions.
You hold the bar on performance with care — you have hard conversations early, address underperformance directly, and don't let the bar drift to preserve a relationship.

Nice To Haves

Experience in benefits operations, health insurance brokerage, employee benefits administration, or payroll is a strong plus.
Experience with carrier portals, Salesforce, and high-volume operational tooling is helpful but not required if the leadership and AI fluency are there.

Responsibilities

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 operational signals into action through your leaders.
Manage cross-functional dependencies with Onboarding, Licensed Benefits Advisors, Member Fulfillment, BizOps, and carrier partners — persuading and aligning, not just informing.
Set the AI vision and own the automation roadmap for Group Fulfillment — what gets automated, by when, and what the team's capacity unlocks as a result.
Coach AI fluency through your leaders — run office hours and working sessions, set the bar for your managers, and partner with Data, Engineering, and Product to shape the tooling that lands in your team's workflow.
Own the rationale before you deliver any meaningful change — running a clear playbook every time: what's changing, why, what it means for the team, what resources are in place, how it gets owned.
Make decisions within your authority quickly, communicate them clearly, and don't reopen them when they meet friction.
Run a calibrated, evidence-based performance cycle that holds a high bar across your team, with AI fluency treated as a non-negotiable expectation
Develop high-potential individual contributors and managers through structured stretch work, cohort programs, and direct sponsorship. Address underperformance early and directly, with the same care and clarity you bring to recognition.