Senior Engineering Manager Onboarding & Activation

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.

As Gusto transitions to an AI-native company, this role will help shape how intelligence is embedded across our Growth platform—from acquisition to onboarding to expansion. You’ll lead engineering efforts that make our systems adaptive, data‑driven, and intelligent by design. This means building not only for scale and reliability, but for learning and continuous optimization—where every part of the funnel can reason, predict, and personalize.

You’ll operate at the intersection of Growth systems, AI capabilities, and platform evolution to help unlock Gusto’s next phase of sustainable revenue growth.

The Onboarding & Activation team accelerates Gusto’s revenue growth by designing, innovating, and experimenting with the most critical acquisition paths—the customer onboarding experience. We’re obsessed with building a customer‑centric experience that not only helps customers reach payroll setup (conversion) but also ensures awareness and setup of other products (activation) they need. We’re reimagining our onboarding experience, evolving it from a single‑product journey to a multi‑product onboarding journey.

Our focus is shifting from deterministic user journeys to intelligent growth systems—ones that understand intent, tailor experiences, and continuously improve through data and feedback.

• Build and foster an inclusive, collaborative, and impact‑oriented culture.
• Collaborate closely with Product, Design, and Data Science to define, iterate, and execute on initiatives contributing to revenue growth.
• Champion AI‑native patterns in the Onboarding platform—designing for learning loops, feedback‑driven iteration, and safe model usage in customer‑facing contexts.
• Help establish and guide the team on best practices for experimentation, evaluation, and observability in AI‑augmented Growth experiences.
• Collaborate with AI platform and Data Science teams to integrate model‑driven insights into onboarding workflows—such as personalization, intelligent package recommendations, and AI‑driven experiences that answer user questions while helping them accomplish tasks.
• Engage with all development teams across Gusto to align and drive toward long‑term maintainability and stability of our systems.
• Mentor and provide guidance to individual team members, fostering growth and development.

• 12+ years of professional software development experience.
• 5+ years of engineering management experience, preferably revenue‑driving, Product engineering, or Growth teams.
• Experience managing multiple teams and managing Engineering Managers.
• Curiosity and ability to operate in an AI‑native environment—integrating intelligence, automation, and experimentation into how we grow the business.
• Experience in highly cross‑functional environments for highly complex products.
• Experience scaling Engineering organizations.
• Nice to have:
  • Experience building and maintaining onboarding experiences and package recommendations.
  • Experience in experimentation and user‑experience optimization.
  • Experience working cross‑functionally with Revenue teams.
  • Experience incorporating AI and ML into product experiences.

Our cash compensation for this role is targeted at $220,000 – $275,000 for San Francisco, New York, and Seattle; $205,000 – $255,000 in Los Angeles; $185,000 – $235,000 in Denver; and $200,000 – $250,000 CAD for Toronto, Canada. Final offers are determined by factors including candidate experience and expertise. Gusto has offices in Denver, San Francisco, and New York City; employees in these locations are expected to work from the office 2‑3 days per week (or more depending on role).

Remote work…