Similar Jobs at Gusto
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.
About the Role:
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.
About the Team:
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 get across the finish line of payroll setup (ie. Conversion), but also ensuring awareness and setup of other products (ie. Activation) that the customer needs.
We’re in an exciting phase of reimagining our onboarding experience, evolving it from a single-product focused journey to a multi-product onboarding experience.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.
We’re looking for a strategic and motivated engineering leader to empower and scale the Onboarding & Activation team that is building Gusto’s next big thing!
Here’s what you’ll do day-to-day:
- 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 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’s questions while helping them accomplish their 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.
Here’s what we're looking for:
- 12+ years of professional software development experience
- 5+ years of engineering management experience, preferably revenue-driving teams Product engineering teams or Growth teams
- Experience managing multiple teams, and managing EMs
- 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 in 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 amount 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 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. 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 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.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
Gusto San Francisco, California, USA Office
Gusto's San Francisco office is located in a vibrant, up-and-coming area nestled between Potrero Hill and the bay. Formerly a shipbuilding hub dating back to the 1800s, this dockside area retains an industrial vibe. Gusties drive, bike, or take public transportation to our office.
What you need to know about the San Francisco Tech Scene
Key Facts About San Francisco Tech
- Number of Tech Workers: 365,500; 13.9% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Google, Apple, Salesforce, Meta
- Key Industries: Artificial intelligence, cloud computing, fintech, consumer technology, software
- Funding Landscape: $50.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Sequoia Capital, Andreessen Horowitz, Bessemer Venture Partners, Greylock Partners, Khosla Ventures, Kleiner Perkins
- Research Centers and Universities: Stanford University; University of California, Berkeley; University of San Francisco; Santa Clara University; Ames Research Center; Center for AI Safety; California Institute for Regenerative Medicine
