Gusto
Fintech · Payroll
- HQ
- San Francisco, US
- Founded
- 2011
- Website
- gusto.com
Currently tracking 13 active AI roles, up 30% versus the prior 4 weeks. Primary focus: Agent · Engineering. Salary range $99k–$321k (avg $212k).
Gusto currently has 20 active AI-related job listings. The majority of these roles, 85%, are focused on agents, with the remaining 15% in application. The top hiring functions are Engineering, with 11 roles, and Product, with 9 roles. Hiring is primarily concentrated in the United States, with one role in Canada. Frequently mentioned tech tags include agent orchestration, LLM observability, and guardrails, suggesting a focus on managing and integrating AI agents.
Gusto currently has 19 active AI-related roles in our index. The most common open titles are: Enterprise Application AI Architect, Head of Design, Unified Service Platform, Head of ML/AI Engineering, Legal & Compliance Tech IT Product Manager, Platform Operations Analyst. Most positions are in Engineering and Product.
Gusto's active AI hiring is concentrated in: agents (79%), application (21%). These categories follow a seven-stage AI lifecycle: data, pre-training, post-training, serving infrastructure, agents, evaluation, and application.
Gusto is hiring AI talent in: United States (18 roles), Canada (2 roles).
Job postings at Gusto most frequently mention: Machine Learning, Production ML Systems, Content Generation, Product Management, Product Impact.
In the past 30 days, Gusto has posted 10 new AI-related roles. That is a +67% change versus the prior 30 days (6 → 10).
| Title | Stage | AI score |
|---|---|---|
| Sr. Staff AI/ML Engineer Sr. Staff AI/ML Engineer responsible for designing, building, and scaling the AI platform that empowers Gusto's internal teams to build intelligent agents and deliver customer value. This includes developing core platform capabilities such as agent orchestration, RAG infrastructure, eval tooling, model serving, prompt management, observability, and safety guardrails. The role involves owning the full lifecycle from problem framing to production deployment, ensuring the platform is reliable, performant, and easy to adopt. The Staff MLE will also shape technical standards, drive architectural decisions, and mentor engineers. | AgentServe | 9 |
| Product Manager, Unified Service Platform Product Manager for an AI-First Service Platform focused on building an intelligence layer for customer service. This involves owning capabilities like intent understanding, escalation decisions, context ingestion, and knowledge retrieval for voice, chat, and email channels. The role requires building and refining models, defining evaluation frameworks, dismantling legacy systems, and collaborating with various teams to improve customer experience and operational efficiency through AI-native agentic solutions. |
| AgentEval Gate |
| 8 |
| Legal & Compliance Tech IT Product Manager Product Manager for Legal & Compliance Technology at Gusto, focusing on an AI-first strategy to embed generative AI, AI agents, and intelligent automation into enterprise applications. The role involves owning the product roadmap, designing AI-augmented workflows, and integrating LLMs with legal systems using RAG and MCPs. | Agent | 8 |
| Staff Software Engineer, AI Developer Tools Staff Software Engineer on the AI Developer Tools team at Gusto, responsible for architecting the AI platform to accelerate engineering across the organization. Focuses on multi-agent systems, RAG, and intelligent automation to eliminate developer friction and improve productivity. | AgentServe | 8 |
| Strategic Operations Lead This role is responsible for building and operating 'Benefits Labs', a system that governs how Gusto's Benefits organization tests, validates, and scales operational change. The role is AI-native, focusing on designing and running AI agents, automations, and workflows for tasks like triaging work, executing pilots, and synthesizing evidence, with the goal of creating a highly leveraged system that minimizes manual intervention. | Agent | 8 |
| Head of ML/AI Engineering Gusto is seeking a strategic Head of AI/MLE to lead their AI/ML organization, define the company's AI/ML strategy, and shape the development and deployment of AI-native products and systems. This role involves unifying classical ML and GenAI, maturing the ML platform, and ensuring production systems meet high standards for reliability, safety, and maintainability. The leader will manage teams including ML Engineering, ML Platform, Risk Data Science, and AI Scientists, and partner with senior stakeholders to drive customer and business impact through AI. | ShipServe | 8 |
| AI Solutions Architect The AI Solutions Architect will design, prototype, deploy, and continuously improve AI-driven agentic workflows for service operations at Gusto. This role involves architecting end-to-end agentic service workflow frameworks, designing multi-agent orchestration patterns, and influencing AI platform capabilities. The architect will also ensure AI governance, translate CX quality stakes, and strengthen evaluation frameworks, working closely with Engineering, CX, Legal, and Compliance. | AgentServe | 8 |
| Head of Client Experience, Symmetry This role leads the transformation of client experience at Symmetry (part of Gusto) by defining and executing a vision for agentic-powered client support. The Head of Client Experience will partner with Product and Engineering to integrate AI products, build 24/7 AI-powered support, and enhance team efficiency with AI and automation, while maintaining a human touch and client empathy. The role requires a technical builder with proven AI fluency and experience in leading teams and driving operational transformation. | Agent | 8 |
| Principal Product Manager, AI Enabled Workforce This role is for a Principal Product Manager focused on building an AI-native, agentic platform to enhance internal workforce productivity and customer experience. The individual will architect a "System of Intelligence" and "Digital Exoskeleton" to automate tasks, provide real-time assistance, and create a symbiotic AI-Human-AI loop, transforming how GTM and Service teams operate. | Agent | 8 |
| Head of AI-Native Talent Systems Gusto is seeking a Head of AI-Native Talent Systems to redesign how people grow within an AI-native company. This role focuses on building systems for onboarding, feedback, performance reviews, and promotions, using AI as a practical tool for reflection, coaching, and skill-building. The goal is to make growth obvious, continuous, and integrated into the flow of work, ultimately creating an AI-powered environment where development is a natural byproduct of doing the job. | Agent | 8 |
| WFM Capacity & Analytics Planner Gusto is seeking a senior, technically minded workforce management planner to design and scale AI-powered forecasting and capacity planning systems. The role involves building frameworks, pipelines, and governance structures to enhance WFM operations. Responsibilities include using AI to identify demand shifts, connecting AI insights to operational decisions, developing capacity plans, building AI-powered data pipelines, and designing governance frameworks for AI-enabled WFM workflows. The ideal candidate has demonstrated ability to operationalize AI tools in a WFM context, strong analytical skills, and experience building data pipelines. | Agent | 7 |
| Head of Design, Unified Service Platform Head of Design for Gusto's Unified Service Platform, focusing on AI-native service design. This role involves leading a team of designers, setting design direction, and staying hands-on with high-leverage design work. The primary focus is on defining and building AI-native customer support experiences, including AI-driven support, multi-channel service, and human-AI collaboration. | Agent | 7 |
| Principal Product Operations Manager This role focuses on integrating AI into customer service operations, specifically by building and deploying AI-powered workflows and agentic systems to improve efficiency and customer resolution. The Principal Product Operations Manager will lead service design, identify AI leverage points, and ensure new products and features are launched with robust service support, acting as a strategic lead at the intersection of Product and Customer Experience. | Agent | 7 |
| Retirement AI Staff Engineer Staff Engineer role focused on building and shipping production AI features for Gusto Retirement, specifically using LLMs for customer-facing experiences. Requires strong software engineering skills, hands-on LLM implementation experience (RAG, agents, tool loops), and end-to-end ownership of features. | Agent | 7 |
| Staff Software Engineer, Growth (Revenue Enablement) Staff Software Engineer, Growth (Revenue Enablement) at Gusto. This role focuses on building and operating AI-powered customer acquisition, onboarding, and lifecycle engagement experiences. Key responsibilities include developing an AI Voice Agent for onboarding and scaling AI-driven email systems using an LLM content generation engine. The role requires full-stack development, ownership of production workflows, and measurable customer impact. | AgentServe | 7 |
| Senior Staff IT Controls, Enterprise Applications Senior Staff IT Controls role focused on evolving and scaling IT General Controls (ITGCs) across enterprise applications. The role will pioneer the use of AI and automation, including LLM-based evidence review and agentic control testing, to transform assurance into a scalable, intelligent capability. This involves building AI-native continuous controls monitoring and governing internal AI builds to ensure they meet control standards. The role requires deep IT controls expertise combined with a vision for AI-augmented assurance and SOX 404 compliance. | AgentEval Gate | 7 |
| Staff Software Engineer, Platform Orchestration Staff Software Engineer, Platform Orchestration role focused on building an internal platform that enables engineers to ship production-grade systems. A key aspect is developing the AI-agent surface for this platform, allowing agents to safely drive infrastructure and deployment workflows. | Agent | 7 |
| Legal AI Engineer (Contractor) This role is for a Legal AI Engineer on a fixed-term contract to build foundational AI infrastructure for a legal team. The engineer will design, implement, and document AI systems and workflows, including a structured knowledge layer and AI-assisted processes for contract review and matter intake. The goal is to turn experiments into robust, shared systems that can be maintained internally after the engagement. | Agent | 7 |
| Senior Product Manager, Document Studio Senior Product Manager for Gusto's Document Studio, an AI-powered platform that helps small business owners generate personalized and compliant HR documentation for various situations like new hires, compensation changes, and terminations. The role involves owning the product strategy, roadmap, and execution for the entire end-to-end experience, including the Handbook product, document templates, employer-facing manager, employee experience, and the underlying platform. The PM will partner closely with engineering, design, Legal, and Compliance, leveraging AI tools to automate processes and deliver customer value. | Agent | 7 |
| Principal Data Scientist, Payments Principal Data Scientist on the Payments team at Gusto, focusing on integrating AI into financial infrastructure. The role involves owning payments intelligence, driving experimentation, building predictive models for failure and risk, and developing AI-native data products. Requires strong SQL, Python, experimentation expertise, and experience with payments domain knowledge. The role emphasizes building AI as a core component and responsible AI use in a regulated financial context. | AgentData | 7 |
| AI Manager, Compliance Systems Manager role focused on building AI-powered compliance systems from scratch, involving designing architecture, deploying and managing AI agents for various compliance use cases, and ensuring human oversight. The role requires hands-on experience with AI tools, agent orchestration, prompt engineering, and operating within a regulated fintech environment. | Agent | 7 |
| Staff Product Designer, Benefits Staff Product Designer for the Benefits team at Gusto, focusing on designing and launching a new AI-native product offering. The role involves leading discovery, designing end-to-end service experiences, creating AI-assisted decision moments, defining systems for AI safety and scalability, making data operational for AI collaboration, and building feedback loops to improve AI quality. The designer will also use AI-assisted dev tools for prototyping and delivery. | Agent | 7 |
| Principal Product Manager, Agentic Benefits Operations Product Manager to lead the transformation of Gusto's benefits administration platform, focusing on agentic workflows, customer-facing experiences, internal tooling, and carrier integrations. This role requires strategic thinking, collaboration across functions, and accelerating execution in an AI-first world. | Agent | 7 |
| Staff Product Designer - Time Tools Product Designer role focused on the Time Tools team at Gusto, with a strong emphasis on designing AI-native experiences for small business owners and employees. The role involves defining how users interact with AI-generated outputs, ensuring human control and safety, and shipping end-to-end product experiences. | Ship | 7 |
| Senior Engineering Manager, Symmetry Product Development Seeking a seasoned engineering leader to manage a product development team focused on leveraging AI for payroll infrastructure. The role involves supporting existing core products, advancing AI integration across the product portfolio and SDLC, and transforming shared services like DevOps and QA to be AI-native. The goal is to drive innovation, increase engineering velocity, and ensure AI is a key differentiator. | Ship | 7 |
| Principal Product Designer, CoreX AI Principal Product Designer to lead AI design across Gusto, defining AI's interaction model, UX principles, and product direction. This role is strategic and hands-on, shaping AI-powered workflows, ensuring user trust, and shipping customer-facing AI capabilities. The designer will work with senior leaders to define the AI portfolio and establish scalable AI interaction patterns. | ShipAgent | 7 |
| Principal Product Manager, Customer Onboarding Product Manager role focused on developing an AI agent to improve customer onboarding for Gusto's payroll and expansion services, aiming to increase conversion rates by simplifying and clarifying the process. | Agent | 7 |
| Enterprise Application AI Architect This role focuses on integrating AI and automation into Gusto's enterprise applications, specifically designing and managing AI agents and Model Context Protocols (MCPs) to make internal systems smarter and more autonomous. The goal is to transform reactive workflows into predictive, self-improving platforms, ensuring security, compliance, and measurable impact within the IT and Enterprise Applications organization. | Agent | 7 |
| Sales Operations Analyst This role focuses on building AI-powered solutions and automations to enhance the productivity of a sales organization. The analyst will identify, prototype, and embed AI tools into daily workflows, working with various teams to drive efficiency and effectiveness in sales processes. While AI is a core part of the company's operations and this role involves driving AI strategy, the primary function is not to build core AI models but to leverage and integrate AI tools for sales operations. | — | 5 |
| Expansion Account Executive This role is for an Expansion Account Executive at Gusto, a company that provides payroll, benefits, and HR services for small businesses. The role involves driving expansion revenue by engaging customers through inbound and outbound outreach, using a structured cadence and AI-powered workflows. Key responsibilities include conducting consultative calls, demonstrating product value, updating Salesforce, and meeting a monthly ARR quota. The role requires 3+ years of consultative sales experience, proficiency in Salesforce and sales engagement tools, and proven day-to-day experience integrating AI into sales workflows (writing, research, prep, summarization) with a track record of providing feedback to improve AI tools. | — | 5 |
| Resource Management & Analytics, WFM This role is for a Workforce Management Analyst at Gusto, focusing on optimizing contact center operations through strategic planning, performance interpretation, and building next-generation WFM tooling. The role requires AI fluency and hands-on experience with AI tools for automation, such as alert systems and workflow integrations, to scale capacity and reduce manual effort. It involves interpreting performance signals, making strategic staffing decisions, managing schedules, and serving as a system administrator for WFM tools. The position emphasizes proactive thinking, data-driven insights, and collaboration within a team-oriented environment. | — | 5 |
| Treasury Manager This role is for a Senior Treasury professional at Gusto, responsible for managing financial resources, cash/liquidity management, and banking initiatives. The role involves liaising with internal teams and external partners, building enhanced liquidity forecasting tools, modeling liquidity usage, developing cost of funds programs, exploring new product offerings, and managing money movement/payment types including stable coins. A key aspect is the "AI native approach," requiring in-depth experience using AI to solve corporate treasury needs, improve workflows, and create efficiencies. | — | 5 |
| Enablement Manager, Partners This role is responsible for developing and executing the enablement strategy for Gusto's channel partners, focusing on onboarding, continuous education, and resource provision. The role requires defining enablement methodologies, advising leadership on strategy, and driving cross-functional alignment. A key aspect involves researching and applying emerging AI tools to enhance program design and delivery, and contributing to Gusto's point of view on AI in partner enablement. | — | 5 |
| Payroll and Taxes Customer Care Advocate This role is for a Payroll and Taxes Customer Care Advocate at Gusto. The primary responsibilities include providing exceptional customer service to small business owners regarding payroll and tax products, troubleshooting issues, and communicating product updates. The role requires experience in the payroll industry, a customer-focused approach, and strong problem-solving skills. While AI is fundamental to Gusto's operations and employees are expected to engage with AI tools, this specific role is customer-facing and does not involve building or directly managing AI models. | — | 5 |
| Expansion Account Manager, PE This role is for an Expansion Account Manager at Gusto, a company that provides payroll, benefits, and HR services to small businesses. The role focuses on leading and developing a team to drive revenue growth, customer retention, and expansion through upselling and cross-selling. While the company emphasizes the use of AI tools in daily work, the core responsibilities of this role are sales leadership, strategy, and operational excellence, not the direct development or deployment of AI models. | — | 5 |
| Event Marketing Manager Event Marketing Manager responsible for designing, producing, and optimizing event marketing programs, including trade shows, conferences, and Gusto-owned activations. This role will collaborate with cross-functional teams, manage budgets and timelines, build relationships with external partners, and leverage AI tools to enhance event marketing workflows. | — | 5 |
| Staff Software Engineer, Tax Accounts Staff Software Engineer for Gusto's Tax Accounts team, focusing on building and maintaining systems for employer and employee tax accounts, including agency registrations, authorizations, and filings. The role involves full-stack development, automation, and ensuring accuracy in a complex compliance domain. Experience with AI tools for development and testing is a plus. | — | 5 |
| Senior Platform Operations Analyst Senior Platform Operations Analyst role focused on building and scaling financial infrastructure, reconciliation, and control systems. The role involves owning cross-functional projects, partnering with Engineering and Product, and mentoring others. A key aspect is building reusable AI workflows to improve team efficiency and acting as a subject matter expert in applying AI to operations. | Agent | 5 |
| Platform Operations Analyst This role focuses on operational excellence in payments, reconciliation, and loss detection within a fintech company. The analyst will use AI and data tooling to improve processes, automate manual workflows, and gain an end-to-end understanding of financial flows. Key responsibilities include executing reconciliations, investigating discrepancies, partnering with engineering to resolve system gaps, and strengthening documentation. A strong emphasis is placed on demonstrated experience using AI to automate real-world manual workflows and improve operational efficiency. | Agent | 5 |
| Product Designer, HR Experiences Product Designer focused on AI-driven HR experiences, shaping AI-assisted services for both small business owners and HR experts. This role involves designing user experiences for AI-generated outputs, managing uncertainty and errors, and ensuring human oversight in a high-stakes compliance domain. The designer will also leverage AI tools in their own workflow to accelerate design processes. | Ship | 5 |
| Tax Resolution Advocate This role is for a Tax Resolution Advocate at Gusto, a company that provides payroll, health insurance, and HR services to small businesses. The role involves resolving tax notices for customers, acting as a detective and problem-solver, researching tax laws, and collaborating with internal teams and tax agencies. The role emphasizes research, analysis, communication, and problem-solving. The company states that AI is fundamental to how work gets done and expects all team members to actively engage with AI tools relevant to their role. | — | 5 |
| Tax Resolution Advocate This role is for a Tax Resolution Advocate at Gusto, a company that provides payroll, health insurance, and HR services to small businesses. The advocate will resolve tax notices for customers, acting as a detective and problem-solver by researching tax laws and identifying the root cause of notices. They will collaborate with tax agencies and internal teams, provide feedback on tools, and use AI tools relevant to their role. The role emphasizes research, analysis, communication, and problem-solving skills, with a focus on customer experience and attention to detail. The team is part of the Payroll, Tax & Compliance Services organization. | — | 5 |
| Staff Software Engineer, Benefit Renewals This is a Staff Software Engineer role focused on building and iterating on product features within the Benefits Renewals team at Gusto. While the role encourages the use and experimentation with AI tools to accelerate development and improve product capabilities, the core craft is full-stack software engineering, not AI/ML model development. The primary output is customer-facing product features and workflow automation. | — | 5 |
| Benefits Advising (Renewals) Manager Gusto is seeking a leader for their Benefits Advising team to provide small business owners and their employees with the best customer experience and expert benefits advice. The role involves leading a licensed benefits advisor organization, empowering individual contributors, and driving customer retention and revenue growth. The leader will also champion AI integration, identifying opportunities and coaching the team to build AI fluency to improve advisor productivity, customer retention, and operational efficiency. | — | 5 |
| Product Counsel - HR Apps/Employment Law Product Counsel role focused on HR Apps, requiring legal expertise in employment law and product counseling. The role involves providing legal support to product and engineering teams, building compliant HR products, and utilizing AI tools for research and process improvement. Success depends on strong organizational skills, a process-oriented mindset, and the ability to manage high volumes of requests. | — | 5 |
| Staff Software Engineer, HR Experiences Staff Software Engineer role at Gusto focusing on HR Experiences, with a significant component of building AI tools and agents to assist HR Partners and automate workflows. The role involves full-stack development across the product lifecycle, mentoring engineers, and collaborating with cross-functional teams. Experience with agentic coding tools and building agents is highlighted. | Agent | 5 |
| Senior Health Insurance Sales Operations Analyst This role focuses on supporting the Health Insurance Sales team by building insights and AI-powered solutions to improve sales strategies and efficiency. The Senior Sales Operations Analyst will identify, prototype, and embed AI and automation tools into daily sales workflows, partnering with various teams to drive process improvements and operational support. The role requires strong analytical skills, Salesforce proficiency, and experience with forecasting and pipeline management, with a focus on enhancing sales productivity through data-driven and AI-assisted approaches. | — | 5 |
| Marketing Programs Specialist, Symmetry This role is an execution-focused marketing specialist who will operationalize marketing strategy into shipped work, focusing on new business acquisition and client/product communications. The role is described as "AI-first" and expects the candidate to use AI tools across all workflows to accelerate content, reporting, or campaign efficiency. It supports Demand Gen and Product Marketing functions, executing against plans set by functional leads. | — | 5 |
| Benefits Escalation Services Manager This role is for a Benefits Escalation Services Manager at Gusto, a company that provides payroll, health insurance, and HR services to small businesses. The manager will lead a team of 10-15 Operations Specialists responsible for benefits administration, working with health insurance carriers. The role involves managing daily operations, coaching the team, driving operational execution, and identifying opportunities to leverage AI tools and automation to improve efficiency. The ideal candidate has experience in Benefits Administration or Health Insurance, leadership experience, and is comfortable using AI tools like LLMs for tasks such as drafting communications and summarizing data. Prompt Engineering experience is a plus. The role is focused on improving customer experience and operational efficiency through technology and AI. | — | 5 |
| Staff Software Engineer, Payroll Canada Staff Software Engineer to join Gusto's Payroll Canada team, building and scaling the payroll experience for Canadian businesses. This is a 0-to-1 opportunity, primarily a backend role involving designing and evolving services and business logic, with full-stack components where logic surfaces to customers via GraphQL. The role requires owning complex technical problems end-to-end, partnering with Product and Platform teams, and bringing Gusto's payroll product to a new country. The role will leverage AI-assisted development tools. | — | 5 |