Senior Engineering Manager Onboarding & Activation

Senior Engineering Manager, Growth (Onboarding & Activation)

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At Gusto, we are 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 customers. With teams in Denver, San Francisco, and New York, we support more than 400,000 small businesses across the country and build a workplace that represents and celebrates the customers we serve.

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, building for scale, reliability, learning and continuous optimization so 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 the most customer‑centric experience that not only helps customers complete payroll setup (conversion) but also ensures activation of other products they need. We’re reimagining our onboarding experience from a single‑product journey to a multi‑product one, shifting from deterministic user journeys to intelligent growth systems 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 onboarding 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 towards long‑term maintainability and stability of our systems.
• Mentor and provide guidance to individual team members, fostering growth and development.

• 12+ years of software development experience.
• 5+ years of engineering management experience, preferably revenue‑driving teams, product engineering teams, or growth teams.
• Experience managing multiple teams and 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 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 range for this role is $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. Final offers vary with experience and other factors.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office approximately 2–3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles,…