Senior Engineering Manager, Gusto
Builder Enablement - Front End
$223-278k
Stock equity is additional
More information about location
2-3 days a week in office
Automated payroll, benefits & HR platform
Job no longer available
Automated payroll, benefits & HR platform
1001+ employees
Job no longer available
$223-278k
Stock equity is additional
More information about location
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy - which many SMB owners don’t have. The co-founders of Gusto all come from small business backgrounds, which is why they created a platform that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and position in a competitive market, including the likes of Ardius, Symmetry and Guideline.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. It continues to expand its platform, for example by partnering with Parafin to launch a payroll line of credit for small businesses, and more recently launching Cofounder, an AI teammate tailored to the needs of small businesses.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Medical, dental, and vision insurance for employees and dependents
- Family care and support, including family planning and fertility benefits
- Gender-affirming care and support
- A variety of mental health resources
- Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more
- Free meals and refreshments at the office (conversation and community is an added bonus!)
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO & Co-Founder)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO & Co-Founder)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo before co-founding Gusto in 2011.
Edward Kim
(Head of Technology & Co-Founder)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing before co-founding Gusto in 2011.
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