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
We’re accelerating Gusto’s revenue growth by innovating, designing, and experimenting with different upsell paradigms such as ML-based recommendation systems, embedded contextual nudges, user intent-driven upsells, human-and-AI hybrid outbound upsells and continuously improving Gusto Store and checkout 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 engineering teams that are 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
- Conduct regular 1:1s with your team members to support their continued growth and learning
- Collaborate with our product management and design teams to define, iterate, and execute on initiatives contributing to Growth’s roadmap to drive revenue growth.
- Partner with Product, Design, Data and others within and outside your team
- Help build and manage team processes and create a culture that enables the team to do its best work
- Provide and receive mentorship and peer support
- Champion AI-native patterns in Growth systems — designing for learning loops, feedback-driven iteration, and safe model usage in customer-facing contexts.
- Help establish best practices for experimentation, evaluation, and observability in AI-augmented Growth experiences.
- Partner with cross-functional teams to tackle complex and ambiguous problems, translating them into engineering solutions that drive our customer acquisition and ACV expansion platform forward.
- Collaborate with AI platform and data science teams to integrate model-driven insights into Growth workflows — such as lead scoring, onboarding personalization, intelligent upsell recommendations, and AI/ML-driven comms platform.
Here’s What We’re Looking For
- 8+ years of professional software development experience, preferably in B2B software and/or growth engineering
- At least 2 years empowering Product or Growth engineering teams
- Preference for experience building and maintaining onboarding funnels, checkout flows, upsell/cross-sell systems or other complex multi-step workflows
- Experience managing and mentoring a software development team
- Ability to work iteratively with data and experimentation driven development, and a record of driving impact reflected in metrics and customer sentiment
- Experience working cross functionally with product, design, data, sales, support, and marketing
- 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 leading a team on designing or implementing product experiences incorporating ML and AI — from recommendations to intelligent onboarding or personalization systems.
- Experience in experimentation and user experience optimization.
- Experience working closely with Revenue teams.
Our cash compensation amount for this role is targeted at $163,000-$204,000 in Denver, $178,000-$223,000 for Los Angeles and most remote locations, $197,000-$247,000 for San Francisco, New York, and Seattle. Final offer amounts are determined by multiple factors including candidate experience, level, 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.
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What the Team is Saying
What We Do
Gusto is a modern, online small business 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.
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.
Why Work With Us
We help small businesses—the backbone of the economy—thrive. Everything we do ladders up to empowering entrepreneurs and supporting their teams. Gusto empowers builders at every level to take initiative and make things better. You'll be solving meaningful challenges that shape the future of work.
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Employees engage in a combination of remote and on-site work.
We’ve built an inclusive, connected culture—no matter where you live. Whether near an office or remote, you’ll find opportunities to connect, grow, and belong. Employees work from the office on 2 designated days per week.
