Benefits Engineering Manager

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 Team:

Come be part of the Benefits group and help small and medium sized businesses make the right choice for themselves and their employees! We have an exciting opportunity for an experienced Engineering Manager to empower part of our BenAdmin team.

As a key member of Gusto’ Benefits leadership team, your role will encompass building a dynamic team and contributing to build a thriving business. You will also be responsible for working collaboratively with other cross-functional teams and leaders to build a suite of products that will be adored by our customers while setting industry benchmarks.

If you are a customer-centric builder who thrives on making a substantial impact within a high-growth organization, we would be thrilled to hear from you!

About the Role:

Gusto Benefits is looking for an experienced Engineering Manager to lead the design, development, and deployment of solutions that enhance our customer experience. In this role, you'll empower a team of Gusties and contractors to architect and deliver solutions that help our CX team deliver on the commitments we’ve made to our customers.

You'll be a key technical voice on the team, helping define how we build, mentor engineers around you, and actively leverage AI and agentic tools to accelerate delivery. The ideal candidate will have a background in integrating artificial intelligence into legacy systems with proven expertise in applying these technologies to improve customer interactions and satisfaction. Be a change agent on how Gusto leverages AI to better serve customers.

Here’s what you’ll do day-to-day:

Lead your engineering team to design, develop, and deploy AI-powered applications to enhance customer and advocate experiences.

Strategic thinking - challenge norms and ask questions!

You will work cross-functionally with engineering, product, design, and stakeholder teams to lead various initiatives to advance our customer service solutions

You will leverage our data to identify key insights and create operational efficiencies, as well as produce accurate and meaningful analysis to drive business decisions

Meet with stakeholders from business and engineering to understand OKR requirements and convert them into analytical solutions

Integrate with third-party platforms (e.g., Salesforce, Zendesk, or similar CRM/support systems) where applicable

Responsible for driving the development of product and core platform in a fast paced, start-up environment

Providing technical leadership in defining the product and platform solutions

Understand customer pain points, devise solutions, and then iterate through prototyping and frequent, successful product launches.

Work cross functionally with design leadership and product management leadership to build and drive Gusto’s product vision and strategy

Empowering a team of senior engineers, architects, and potentially managers to create alignment, clarity, high morale, driving quick but informed decision making, and helping them get unblocked

Here’s what we’re looking for:

10+ years of total relevant technical experience

3+ years of engineering management experience

2+ years in Generative AI demonstrating the ability to leverage AI/agentic tools (e.g., Cursor, Claude or similar) to accelerate development

Nice to Have:

Experience with CRM platforms or third-party integrations (Salesforce, Zendesk, or similar)

Familiarity with Robotic Process Automation (RPA’s)

Prior experience working with contractor-heavy or distributed team structures

Our cash compensation amount for this role is targeted at $223,000-251,000 for San Francisco. 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 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.