AI Manager, Compliance Systems

About Gusto 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 Role: We are looking for someone to build AI-powered compliance systems from the ground up. This is not a role where you inherit a mature platform and maintain it. You will be designing architecture, deploying agents, and engineering the workflows that make compliance faster and more reliable across the Corporate Compliance team. You will need to be comfortable operating in a regulated environment, making judgment calls about what should run autonomously versus what requires human review, and owning the outcomes end to end. Success looks like measurable improvement in automation rates, decision quality, audit readiness, and team enablement. About the Team: The Corporate Compliance team is responsible for ensuring Gusto meets its regulatory obligations across payroll, payments, financial services, and state licensing. We build and maintain the compliance management system that underpins this work, including the compliance controls, obligation monitoring, exam readiness processes, and product launch reviews that keep the business running within regulatory expectations. We do this cross-functionally, partnering closely with Product, Engineering, Legal, Operations, and Risk. Here’s what you’ll do day-to-day: Design and implement AI-native compliance workflows using tools like Claude Code, Codex, Gumloop, and similar platforms Deploy and configure AI agents across compliance use cases, including product reviews, control testing, regulatory change monitoring, licensing workflows, policy governance, and remediation tracking Manage and oversee those agents on an ongoing basis, defining clear boundaries between autonomous execution and human review Monitor agent outputs, decisions, and workflow execution; own operational metrics like task efficacy, accuracy, and regulatory coverage. Identify and address errors, hallucinations, data drift, or unexpected behavior through root cause analysis Own the continuous improvement cycle for agent prompts and decision logic. Conduct root cause assessments, and deploy improvements through structured testing, shadow mode validation, and controlled production rollouts Prototype new agentic frameworks, orchestration layers, and retrieval systems; build evaluation frameworks for accuracy, bias, and explainability Lead analysis of AI metrics, compliance trends, and risk signals to identify systemic gaps and inform roadmap decisions for tooling and automation. Build dashboards and automated reporting that support audits, exams, and executive visibility Serve as the connective tissue between Compliance, Engineering, Product, Legal, Security GRC, and Data and translating regulatory expectations into system logic that ships, while mentoring compliance analysts on AI tool usage, workflow design, and prompt development Here’s what we're looking for: 3-5 years building compliance management systems, regulatory program infrastructure, or technical solutions in a regulated environment (payments, fintech, payroll, or compliance-heavy SaaS). You have taken evolving requirements and turned them into durable processes, controls, and operating systems that scale Hands-on experience leading AI or automation projects from concept through implementation, including human-in-the-loop workflows Comfortable using AI tools (Claude, ChatGPT, Cursor, or similar) for workflow design and debugging; familiar with agent orchestration, prompt engineering, and structured testing Strong cross-functional collaboration skills with a proven history work ... (truncated, view full listing at source)