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 recruitment, hiring, and empowerment of a world-class team
Collaborate closely with AI Scientists and AI Product Managers to create proactive and efficient sales motions with AI
Lead your engineering team to design, develop, deploy AI-powered applications enhancing customer/advocate experiences
Work cross-functionally with engineering, product, design, stakeholders to advance customer service solutions
Leverage data for insights creating operational efficiencies; produce accurate analysis driving business decisions
Meet stakeholders from business/engineering to understand OKR requirements converting them into analytical solutions
Integrate with third-party platforms (e.g., Salesforce, Zendesk or similar CRM/support systems) where applicable
Drive development of product/core platform in fast-paced startup environment
Provide technical leadership defining product/platform solutions
Understand customer pain points; devise solutions; iterate through prototyping & frequent successful launches
Work cross-functionally with design/product leadership building/driving Gusto’s product vision & strategy
Empower senior engineers/architects/managers creating alignment/clarity/high morale; drive quick informed decisions; unblock teams

Here’s what we’re looking for:

10+ years total relevant technical experience
2+ years engineering management experience
2+ years Generative AI experience leveraging AI/agentic tools (e.g., Copilot, Cursor) accelerating 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 teams

Compensation: Cash compensation targeted at $197,000 - $235,000 for San Francisco location; final offer depends on candidate experience/level/expertise.