CX Chief of Staff - Benefit Operations

Denver, CO About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: The Chief of Staff to the Head of Benefit Operations is a senior operator responsible for turning strategy into durable execution by designing and owning the operating systems that allow the organization to scale. This role exists to increase clarity, accountability, and momentum by reducing reliance on ad hoc coordination and individual heroics in a complex, fast-moving environment. Operating with a systems-first, AI-aware mindset, the Chief of Staff uses automation and well-designed workflows to improve decision quality, execution speed, and organizational resilience. Working closely with cross-functional partners, this role ensures high-priority initiatives are aligned, tradeoffs are clear, and the organization can sustain progress through change. Success in this role is measured by better decisions, fewer escalations, and operating systems that continue to run effectively without constant intervention. This is a leadership role that works closely with cross-functional teams to support high-priority initiatives, align teams around shared goals, and ensure continuity through change. As part of a fast-paced, high-growth environment, the Chief of Staff will have the opportunity to help shape and scale a high-performing Benefits organization while directly influencing outcomes and driving transformation. Here’s what you’ll do day-to-day:

Partner with the department head to shape strategy and translate it into clear priorities, operating rules, and execution plans.
Act as a strategic advisor to leadership, providing guidance on decisions, trends, and growth opportunities.
Design, run, and continuously improve the BenOps operating cadence (OKRs, performance reviews, leadership rhythms), with a focus on automation and explicit ownership for clarity,...
Lead change management initiatives by setting clear expectations,...
Design,...
Oversee centralized intake...
Use data-driven insights...
Provide interim leadership coverage...
Own executive-ready narratives...
Enable senior managers...

Here’s what we're looking for:

10+ years of total experience in analytical,...
5+ years in a CX Strategy or Senior-Level CX Operating Experience
Experience as CoS or CX Strategy lead in a large tech company...
Exposure to scale of 1000+ employee organizations...
Business builder mindset: experience designing...
Demonstrated ability to advise...
Strong program leadership: ability to lead complex cross-functional initiatives...
Systems-first orientation: experience building durable workflows...
Comfort operating at multiple altitudes — from executive narrative...
Judgment over heroics: knows when to execute directly...
Clear concise communicator who keeps stakeholders aligned...
Deep empathy for small business customers ...
High integrity curiosity resilience; brings energy without burning out...
AI fluency: hands-on experience using AI or automation ...
Prior chapter outside of Tech is a plus, especially in regulated or service-oriented environments

The target level for this role is Level 5. Our cash compensation range for this role is:

$152000 to $179000 in Las Vegas Denver Orlando
$178000 to $210000 in San Francisco New York

Final offer amounts are determined by multiple factors including candidate location experience expertise may vary from level amounts listed above. Gusto has physical office spaces in Denver San Francisco New York City. Employees based there expected work from office approximately 2–3 days per week (or more depending on role). Same office expectations apply all Symmetry roles Gusto's subsidiary whose physical office is Scottsdale. Note: San Francisco office expectations encompass both San Francisco San Jose metro areas. When approved work from location other than Gusto office secure reliable consistent internet connection required including non-office days hybrid employees. Our customers come from all walks life so do we.... Gusto proud equal opportunity employer.... Personal information collected processed part Gusto application subject Gusto's Applicant Privacy Notice.