AI Manager, Compliance Systems

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.

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.

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.

• →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

• 5-7 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 working across Product, Engineering, Compliance, and Risk
• Demonstrated good judgment in ambiguous, high-stakes situations. You can make a call when the regulatory picture is not perfectly clear and explain your reasoning to stakeholders who are not compliance experts
• Strong data-driven reasoning skills. You are comfortable owning both operational metrics and using them to drive decisions, not just reporting on what happened, but identifying what to change
• You do not need to be a career compliance professional, but you do need to understand how to operationalize regulatory compliance through scalable compliance management systems

Our cash compensation amount for this role is $110,640/yr - $136,456/yr in Denver & most major metro locations, and $133,615/yr - $164,792/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.