Head of People Technology

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy. 

About the Role:

As the Leader of People Technology, you will lead the transformation of Gusto’s internal HR systems and processes with a strong AI-first mindset. Reporting to the Head of IT, you’ll oversee a multidisciplinary team of analysts, technologists, and strategists dedicated to designing scalable, intelligent solutions that support the full employee journey.

The PeopleTech team partners deeply with HR leadership to co-create tools and systems that unlock speed, clarity, and capacity across Gusto’s People operations. From recruiting to payroll, talent development to total rewards, this role helps power the systems behind how we take care of Gusties. We’re looking for a leader who’s excited by transformation—and sees AI as a way to amplify human potential, not just automate tasks.

This is a key leadership role that requires strategic vision, practical systems knowledge, and a strong orientation toward experimentation and scale.

Here’s what you’ll do day-to-day:

• Own the PeopleTech vision and roadmap, with AI as the through line across systems, processes, and priorities
• Build and lead a high-performing team that blends system expertise, business acumen, and curiosity
• Partner across Invite (Recruiting), Payroll, Total Rewards, and HR Ops to co-design technology that increases clarity and reduces operational friction
• Guide the design and rollout of intelligent workflows, leveraging GenAI, automation, and self-serve tools
• Champion a team operating model that balances transformation (50%), enhancements (20%), and AI-driven exploration (30%)
• Evolve legacy processes and systems toward flexible, predictive, and insight-rich architecture
• Promote AI literacy across the People team by embedding guidance, learning, and nudges into daily tools
• Ensure systems meet privacy, security, and compliance requirements at scale
• Launch and scale internal “Gusto on Gusto” PeopleTech use cases that model the future of work
• Act as a thought partner and advisor to People and IT leaders, translating vision into reality

Here’s what we're looking for:

• Bachelor’s degree in Information Systems, Human Resources, Computer Science, or a related field. Advanced degree (MBA or equivalent) preferred
• 10+ years of experience in PeopleTech, HRIS, Business Applications, or IT leadership roles
• 5+ years leading teams that manage complex HR systems, ideally in tech or high-growth environments
• Demonstrated experience applying AI, GenAI, or workflow automation to modernize HR technology and unlock new capabilities
• Hands-on knowledge of Workday, and familiarity with systems like Greenhouse, Lattice, Qualtrics, and Workato
• Strong collaborator and communicator able to drive alignment across HR, IT, and Security
• Systems thinker who knows how to architect for scale, security, and insight
• Practical experience managing risk and compliance within HR systems
• Strategic and execution-oriented leader who inspires trust and builds teams grounded in learning and experimentation

Our cash compensation amount for this role is targeted at $157,000-185,000 in Denver & most remote locations, and $185,000-218,000 in New York & San Francisco Bay Area. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate 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, 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.

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 and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.