Senior Engineering Manager, Builder Enablement - Front End

About Gusto At Gusto, we're 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 their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: As the Senior Engineering Manager for Builder Enablement, you will lead the team that defines how every builder at Gusto — engineer, designer, PM, and increasingly, AI agent — ships high-quality products. Your team owns Gusto's design system (Workbench) and the AI tooling that teaches humans and LLMs how to use it: MCP servers, agent skills, prototyping sandboxes, eval systems, and the prompts and patterns that make AI-assisted shipping feel effortless and trustworthy. This is a highly visible, org-shaping role. The choices your team makes ripple across every product surface at Gusto — from the quality of a token, to how a new hire ramps up, to how AI agents compose production UI. You'll grow senior engineers, partner with Design and Product leadership to set direction, and lead a team running fast weekly experiments in one of the most rapidly evolving parts of frontend engineering. If you're an engineering leader who gets energy from force-multiplier work, who can hold a strong point of view on design systems and on where AI is heading, and who wants to lead a team that's rewriting what "frontend platform" means in an AI-native company — we'd love to talk. About the Team: Builder Enablement's mission is to make high-quality, AI-assisted shipping the default for every builder at Gusto. We're a tight-knit cross-functional team (engineering, design, product) recently re-chartered from Design Systems to reflect a broader scope: roughly 70% AI tooling and builder enablement, 30% design system maintenance and evolution. On any given week the team is shipping new Workbench components and accessibility improvements; MCP servers and agent skills that teach Claude Code and Cursor to use our system correctly; prototyping environments that let designers build realistic experiences with production components; eval systems that measure AI output quality against design system standards; and office-hours support for the hundreds of engineers and designers across Gusto who build on our surfaces every day. This team is a great place for someone who wants leverage — almost every investment here compounds across the company — and who finds it energizing to work at the intersection of design, engineering, and AI. Here’s what you’ll do day-to-day: Lead and grow a team of senior engineers working at the frontier of design systems and AI-assisted development, setting a high bar for technical quality and velocity Partner with the team's Design and Product leads as the engineering half of the team's leadership triad, setting strategy for how AI tooling, the design system, and builder support evolve together Guide the team's use of AI across their own workflows — running and learning from weekly experiments, building evals, and making judgment calls about where to invest in tooling vs. authoring vs. automation Conduct regular 1:1s, coaching, and career development for direct reports, and model Gusto's values across your team and the broader org Collaborate with other engineering leaders across Core Experiences and the AI platform to align on shared tooling, publishing infrastructure, and platform direction Represent Builder Enablement with senior leadership, partner teams, and the broader builder community: running office hours, making crisp tradeoff calls in support threads, and advocating for your team's priorities Own the team's technical strategy at a directional level — adoption of AI ecosystems (MCP, agent skills, eval frameworks), design system architecture, accessibility standards, and publishing/release tooling Here’s what we're looking for: 8+ years of professional software engineering experience, with at least 5 years leading engineering teams A track record of empowering senior engineers and tech leads Strong product sense and the ability to work closely with Design and Product partners to shape strategy, not just execute against it Hands-on fluency with modern AI developer tooling (MCP servers, agent skills, Claude Code / Cursor, prompt engineering, evals) Experience with frontend platforms, design systems, or horizontal/shared infrastructure that many other teams depend on; comfort with TypeScript, React, and modern frontend ecosystems Experiment-driven leadership style: comfortable framing hypotheses, scoping small tests, and making decisions based on evidence in a fast-moving space Strong written and verbal communication: comfortable being visible, educating broadly, and making your team's work legible to non-technical audiences Comfortable navigating ambiguity, fluctuating requirements, and a large stakeholder surface area: the team's customers are the whole company Please note that travel to Gusto’s Denver office for onboarding is required for this position. If you have any questions regarding this requirement, please share with your recruiter. Our cash compensation amount for this role is targeted at $189,000/yr to $236,000/yr in Denver & most remote locations, and $223,000/yr to $278,000/yr for San Francisco, Seattle & New York. 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. 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.