This role is designed for a high-level operations professional with at least 10 years of experience, specifically within high-growth tech environments. The idea
Work type: onsite
Location: Denver, CO
Salary: $152,000 – $179,000/yr
Type: Full-time
This role is designed for a high-level operations professional with at least 10 years of experience, specifically within high-growth tech environments. The ideal candidate has spent significant time (5+ years) in Customer Experience (CX) strategy or leadership and possesses a "systems-first" mindset. You should be someone who isn't just looking to manage existing processes but is eager to build scalable operating models using automation and AI fluency. The position offers a strong compensation package ($152k–$179k in Denver) and the chance to influence a 1,000+ person organization. While the role is based in Denver, Gusto follows a hybrid model requiring 2–3 days per week in-office. You will gain massive visibility by acting as a strategic advisor to the Head of Benefit Operations, translating high-level strategy into durable, automated execution plans. **You might be a good fit if you:** * Have a background in CX strategy or operations within a large, regulated tech company. * Prefer building automated workflows and durable systems over "heroics" or manual coordination. * Are comfortable navigating the complexities of both exempt and non-exempt workforces. * Can switch seamlessly between high-level executive narratives and hands-on data analysis/problem-solving.
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. Learn more about our[ Total Rewards philosophy](https://gusto.com/about/careers/total-rewards).
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: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:
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 daysper week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's 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 it's 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](https://docs.google.com/forms/d/e/1FAIpQLSdEfl7Bp-Twz7LLlhGlha46CrxZ9Kacgakmarf3K2TbnaEgKQ/viewform) and a member of our team will get in touch with you.
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Personal information collected and processed as part of your Gusto application will be subject to [Gusto's Applicant Privacy Notice](https://gusto.com/about/careers/applicant-privacy-notice).