Benefits Engineering Manager

The Wrap; San Francisco (CA); Hybrid; USD 197,000 - 235,000; Full time

Job summary

Gusto is seeking an experienced Applications Systems Engineering Manager to lead the design, development, and deployment of AI-enabled solutions that enhance customer experiences. You will empower a team of 6 to architect and deliver reliable, intelligent payoff workflows.

You’ll mentor engineers, collaborate with AI scientists and product managers, and drive rapid, high-quality product launches while applying AI responsibly across customer interactions.

Qualifications

• 10+ years of total relevant technical experience.
• 2+ years of engineering management experience.
• 2+ years in Generative AI demonstrating the ability to leverage AI/agentic tools to accelerate development.

Responsibilities

• Lead Gusto's Go To Market AI engineering team, including recruitment and empowerment of the team.
• Collaborate with AI Scientists and AI Product Managers to enable proactive AI-driven sales motions.
• Lead engineering to design, develop, and deploy AI-powered applications to enhance customer experiences.
• Work cross-functionally with engineering, product, design, and stakeholders to advance our customer service solutions.
• Leverage data to identify insights and create operational efficiencies and drive business decisions.
• Translate OKR requirements into analytical solutions for stakeholders.
• Integrate with third-party platforms (e.g., Salesforce, Zendesk) as applicable.
• Drive development of product and core platform in a fast-paced, startup environment.
• Provide technical leadership in defining product and platform solutions.
• Identify customer pain points, prototype solutions, and launch products successfully.
• Collaborate with design and product leadership to execute Gusto's vision and strategy.
• Mentor senior engineers and architects to maintain alignment and unblock progress.

Skills

Generative AI

Engineering leadership

Software engineering

AI tools

Tools

Salesforce

Zendesk

Job description

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:

The Unified Service Platform's mission is to create seamless connected, efficient and delightful experiences that empower our customers (internal and external) to make informed decisions and be supported throughout their journey. This team operates as a startup-within-a-startup with a high level of ownership around specific problems to solve for our customers.

The Payoffs team sits within this platform and is responsible for building and maintaining the systems that power end-of-lifecycle payroll workflows, including custom routing, intelligent automations, auto-indexing of tax documents, and end-of-year processing. We move fast, care deeply about quality, and are actively investing in AI-driven approaches to make our systems smarter and more scalable.

About the Role:

Gusto is looking for an experienced Application Systems Engineering Manager to lead the design, development, and deployment of AI solutions that enhance our customer experience. In this role, you'll empower a team of 6 to architect and deliver solutions that keep Gusto's payoff workflows running reliably and intelligently.

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. Our mission is to deliver consistently exceptional Customer and Advocate experiences, at scale, across every touchpoint. The ideal candidate will have a background in artificial intelligence, and software engineering, 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 Gusto's Go To Market AI engineering team, including the recruitment, hiring, and empowerment of a world-class team
• Collaborate closely with AI Scientists and AI Product Managers to create a world where the sales motions run proactively and efficiently with AI.
• Lead your engineering team to design, develop, and deploy AI-powered applications to enhance customer and advocate experiences.
• 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
• 2+ years of engineering management experience
• 2+ years in Generative AI demonstrating the ability to leverage AI/agentic tools (e.g., Copilot, Cursor, or similar) to accelerate development

Nice to Have:

• Experience with CRM platforms or third-party integrations (Salesforce, Zendesk, or similar)
• Familiarity with tax or payroll processing domains
• Prior experience working with contractor-heavy or distributed team structures

Our cash compensation amount for this role is targeted at $197,000-235,000 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 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.