Application Systems Engineering Manager

Gusto•San Francisco, NY

5d•$163,000 - $235,000•Hybrid

About The Position

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . About the Team: The Unified Service Platform’s (USP) 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 PayOps 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 payops 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.

Requirements

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 Haves

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

Responsibilities

Lead Gusto’s USP 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