Head of People Technology

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.