Senior Engineering Manager, Builder Enablement - Front End

Gusto, Inc.•San Francisco, CA

15d•$189,000 - $278,000•Hybrid

About The Position

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. 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.

Requirements

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

Responsibilities

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