CX Chief of Staff - Benefit Operations

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 400,000 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.

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.

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.

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
• Lead change management initiatives by setting clear expectations, sequencing work, and holding leaders accountable for adoption
• Design, evolve, and maintain workflows, metrics, and dashboards that leaders actively use to make decisions
• Oversee centralized intake and prioritization of product requests for BenOps, providing clear recommendations on product asks
• Use data-driven insights to improve customer experience and drive continuous improvements across BenOps and CX
• Provide interim leadership coverage when needed, with real ownership for priorities, delivery, and team health
• Own executive-ready narratives and communications that surface tradeoffs, risks, action, and decisions
• Enable senior managers and foster a culture of accountability, engagement, and continuous learning across the organization

What we're looking for

• 10+ years of total experience in analytical, operating roles at high-growth startups
• 5+ years in a CX Strategy or Senior-Level CX Operating Experience
• Experience as CoS or CX Strategy lead in a large tech company, working with CX or Product leaders
• Exposure to scale of 1000+ employee organizations with a mix of exempt + non-exempt workforce
• Business builder mindset: experience designing and scaling operating models
• Demonstrated ability to advise and influence senior leaders on strategy, organizational design, and people topics
• Strong program leadership: ability to lead complex, cross-functional initiatives from ambiguity to measurable outcomes
• Systems-first orientation: experience building durable workflows, operating mechanisms, dashboards, or automation
• Comfort operating at multiple altitudes — from executive narrative and strategic framing to hands-on problem solving
• Clear, concise communicator who keeps stakeholders aligned and decisions moving
• Deep empathy for small business customers and a strong sense of service
• High integrity, curiosity, and resilience; brings energy without burning out the system
• AI fluency: hands-on experience using AI or automation to reduce planning, reporting, or synthesis load
• Prior chapter outside of Tech is a plus, especially in regulated or service-oriented environments

Compensation

The target level for this role is Level 5, and our cash compensation range for this role is $152,000 to $179,000 in Las Vegas, Denver, and Orlando, and $178,000 to $210,000 in San Francisco and New York.

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.