Benefit Services Senior Leader Group Fulfillment

About Gusto

At Gusto were 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 500000 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 youll 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 teams health coverage.

Youll set operational objectives develop and execute policies manage capacity planning and drive outcomes that have a measurable impact on Gustos customers. Youll lead through your leaders coaching them to own their teams hold the bar and drive change rather than transmit it.

Youll also be a senior partner in shaping how AI transforms Fulfillments work at Gusto. Youll 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 Gustos 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 isnt an inconvenience; its a missed prescription a delayed procedure or a stressful call to HR. Customer outcomes are what drive this team. Its where our passion lives and its the standard we hold ourselves to every day.

As an AI-native company we dont just use technology its 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.

Heres what youll 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 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 teams 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 teams workflow.
• Own the rationale before you deliver any meaningful change running a clear playbook every time: whats 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 dont 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.

Heres what were looking for:

Leadership experience

• 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 dont 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. Youve 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 thats 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 dont let the bar drift to preserve a relationship.

Domain-relevant experience (preferred)

• 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.

Our cash compensation amount for this role is $119185/yr to $154940/yr in Denver & most major metro locations. Final offer amounts are determined by multiple factors including candidate location experience and expertise and may vary from the amounts listed above.

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 Gustos 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.

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 its 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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