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 400,000 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 Role:

Gusto is scaling our AI-powered risk function to support a complex, multi-entity business operating in highly regulated environments. As the Enterprise Risk Management Lead, you will own and operate Gusto's Enterprise Risk and Third Party Risk Management programs , built AI-first, designed to scale, and built to enable the business to move fast without breaking things.

This is a People Empowerer (manager) role. You balance hands-on program leadership with managing and developing a team of compliance professionals. You navigate the tension between "doing the work" and "leading the work" , contributing directly to complex, high-impact programs while ensuring your team delivers with excellence.

You are a change agent who influences how automated risk management gets done at Gusto, models AI-enabled ways of working, and helps others grow their own capabilities in the process.

You will champion the adoption of AI, machine learning, and process automation across risk monitoring, control testing, incident management, and reporting , and you will partner with Product, Data Science, and Engineering to make it explainable, adopted, compliant, and scalable.

Here’s what you’ll do day-to-day:

You manage initiatives that are complex in both scope and impact, influencing the strategic direction of Gusto's compliance risk management framework.

You apply a deep understanding of the regulatory landscape and how it intersects with Gusto's business model to proactively design and lead cross-functional risk programs.

You translate complex risk topics into clear, actionable guidance that senior leaders can immediately understand and operationalize.

You lead cross-functional working groups, align divergent perspectives, and drive cohesive progress toward shared goals , with minimal oversight.

As a PE, you balance individual risk and compliance contribution with team leadership.

You manage operations, professional development, resource allocation, and performance , while staying close enough to the work to be a credible, hands-on partner to your team and stakeholders.

You model responsible AI use, and act as a source of knowledge and mentorship , supporting your team's AI journey and helping others apply it responsibly and effectively.

AI-Enabled Risk Operations, Innovation & Transformation

This is how you and your team operate , not a side project.

• Champion the adoption of AI, machine learning, process automation, and advanced analytics to improve risk monitoring, control testing, and reporting across ERM, TPRM, and broader compliance functions

• Lead the integration of AI and automation into every phase of the risk lifecycle: vendor assessments, document ingestion and analysis, continuous monitoring and alerting, risk scoring, prioritization, and trend analysis

• Build intelligent risk monitoring and evaluation systems , including auto-tagging for risk issues, audit requests, and regulatory changes , that improve real-time visibility and eliminate manual effort across the enterprise risk portfolio

• Drive the digitalization of risk tools including RCSAs, KRIs, incident reporting, and audit tracking , transforming periodic, reactive processes into continuous intelligence systems with live leading and lagging indicators that enable real-time decision-making

• Partner with Product, Data Science, and Engineering to define requirements for AI-driven workflows, decisioning engines, and dashboards , ensuring explainability, auditability, and regulatory defensibility of all AI-enabled risk decisions

• Design and build intelligent dashboards and reporting tools that deliver real-time risk visibility and decision-quality insights to senior leadership and cross-functional stakeholders

• Design AI workflows with appropriate validation loops, human-in-the-loop checkpoints, and guardrails , ensuring outputs are reliable, governable, and meet regulatory standards before being used to frame risks, recommendations, or decisions

• Stay current on AI advancements and emerging technologies and proactively integrate new capabilities into team operations to increase velocity and scale

• Model responsible AI use , supporting ICs in their AI journeys and fostering a culture of intentional experimentation, accountability, and continuous improvement

Enterprise Risk Management

• Design, implement, and continuously improve Gusto's ERM framework, ensuring alignment with best practices and Gusto's stage of growth and strategic priorities across all entities

• Define and maintain Gusto's enterprise risk taxonomy, risk appetite statement, and key risk indicators spanning operational, regulatory, technology, financial, and reputational risk domains

• Lead Gusto's Enterprise Risk Management process , driving integration of risk practices across business functions, promoting a proactive risk culture, and ensuring incident management, root cause analysis, and lessons learned are systematically captured in an automated, AI forward way.

• Apply AI-assisted insights to enterprise risk datasets to surface systemic patterns, validate assumptions, prioritize risks, and deliver proactive, data-driven advisory to senior leadership

• Monitor the regulatory landscape (OCC, FDIC, CFPB, SEC, FINRA, GDPR, NIST, ISO, SOC) and leverage AI to proactively incorporate changes before they become compliance gaps

• Act as a key advisor to senior compliance leadership , translating complex risk findings into clear, actionable recommendations with minimal oversight

Third Party Risk Management (TPRM)

• Design, implement, and independently manage a high-impact, AI-first TPRM program with clear milestones, progress tracking, and measurable outcomes across all Gusto entities

• Manage the full third-party risk lifecycle , onboarding and risk profiling, periodic assessments, issue management, corrective action tracking, and offboarding , across suppliers, product partners, contractors, service providers, and cloud service providers , and do so in an AI and automated way.

• Maintain a centralized, authoritative vendor risk inventory and risk register, ensuring real-time visibility into Gusto's third-party risk posture

• Conduct periodic AI-driven audits and reviews of third-party compliance with contractual obligations and regulatory standards, identifying patterns that inform continuous program improvement

• Serve as the central orchestrator across Compliance, Security, Legal, Procurement, IT, and GRC for proactive and reactive third-party incident management

• Own Gusto's TPRM policy and maintain comprehensive documentation , risk assessments, audit findings, corrective actions , ensuring full accountability and traceability

People Leadership & Team Development

• Balance individual compliance contribution with team leadership , managing operations, professional development, resource allocation, and performance while staying close to the work

• Coach and develop ICs toward next

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Location

San Francisco

Employment Type

Full time

Department

Intelligence & Investigations

Compensation

• $230K – $325K • Offers Equity

The base pay offered may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. If the role is non-exempt, overtime pay will be provided consistent with applicable laws. In addition to the salary range listed above, total compensation also includes generous equity, performance-related bonus(es) for eligible employees, and the following benefits.

Benefits

• Medical, dental, and vision insurance for you and your family, with employer contributions to Health Savings Accounts

• Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses (parking and transit)

• 401(k) retirement plan with employer match

• Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)

• Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees

• 13+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick or safe time (1 hour per 30 hours worked, or more, as required by applicable state or local law)

• Mental health and wellness support

• Employer-paid basic life and disability coverage

• Annual learning and development stipend to fuel your professional growth

• Daily meals in our offices, and meal delivery credits as eligible

• Relocation support for eligible employees

• Additional taxable fringe benefits, such as charitable donation matching and wellness stipends, may also be provided.

About the Team

The Intelligence and Investigations team seeks to rapidly detect and disrupt abuse in AI technologies to ensure their safe use. We are dedicated to identifying emerging abuse trends, analyzing risks, and working with our internal partners to implement effective mitigation strategies to protect against misuse. Our efforts contribute to OpenAI's overarching goal of developing AI that benefits all of humanity.

About the Role

As an Intelligence Systems Engineer, you’ll be focused on advancing our Intelligence & Investigations efforts at OpenAI, ensuring the safe and responsible use of AI across our products and services.

We are seeking a self-starter to prototype, develop, and maintain new tools and processes that integrate OpenAI’s models and infrastructure to enable internal teams to make sense of large, open-domain datasets, fight abuse, and inform high-stakes decisions.

You will be a crucial technical bridge between our data scientists and subject matter experts and technical teams like Platform Integrity, Safety Systems, and Research by leading the development of innovative tools and processes that bolster goals in scaled collections, investigations, and analysis.

The ideal candidate has strong analytical and data skills, with a background in both prototyping and building scalable systems that can swiftly detect emerging threats, process vast amounts of information, and deliver insights to stakeholders. We value professionals with outstanding communication skills, a commitment to continuous learning, and who are dedicated to promoting the responsible use of AI.

In this role, you will:

• Prototype, build, and maintain at-scale intelligence systems that detect, triage, and monitor targeted signals from both open-source and internal data

• Analyze requirements and deliver end-to-end solutions that address complex intelligence challenges while ensuring code quality and scalability

• Be a crucial technical bridge between our Intelligence needs and technical teams like Platform Integrity, Safety Systems, and Research

• Contribute to shaping the team’s technical strategy and design user interfaces for non-technical investigators and analysts

• Prototype new applications to automate team workflows and route leads

• Report on scaled impact using advanced data analysis and visualization products

• Work closely with internal stakeholders and address their technical intelligence needs

You might thrive in this role if you have / are:

• Experience in engineering and project management, ideally with a focus on security, intelligence, or data analysis products.

• Strong technical background and proven track record of building and maintaining systems that enable users to make sense of large, open-domain datasets, fight abuse, and inform high-stakes decisions.

• Proficiency in data analysis, SQL / Python, and application of novel AI techniques for problem-solving.

• Demonstrated ability to leverage cross-functional teams, manage complex product ecosystems, and deliver results in a fast-paced and sometimes ambiguous environment.

• Strong belief in & passion for the value of AI in enabling humans to better understand the complexity of the world

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences

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