Currently tracking 17 active AI roles, down 19% versus the prior 4 weeks. Primary focus: Agent · Engineering. Salary range $111k–$321k (avg $220k).
Gusto currently has 25 active job listings related to artificial intelligence. The majority of these roles, 68%, are focused on agents, with application roles making up another 28%. Product and Engineering are the top hiring functions. The company is frequently seeking candidates with experience in agent orchestration, LLM observability, and guardrails.
Gusto currently has 23 active AI-related roles in our index. The most common open titles are: Benefits Engineering Manager, Enterprise Application AI Architect, Head of Client Experience, Symmetry , Head of Customer Referral & Emerging Channels, Head of ML/AI Engineering. Most positions are in Product and Engineering.
Gusto's active AI hiring is concentrated in: agents (70%), application (30%). 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 (23 roles), Canada (3 roles).
Job postings at Gusto most frequently reference: agent orchestration, llm observability, guardrails, model serving, rag.
In the past 30 days, Gusto has posted 6 new AI-related roles. That is a -25% change versus the prior 30 days (8 → 6).
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| Executive Operations - R&D Executive Operations partner for R&D leaders, focusing on operational efficiency, coordination, and project management, with an emphasis on leveraging AI tools to enhance these functions. | — | 5 |
| Manager, Expansion Account Manager This role is for a Manager of Expansion Account Management at Gusto, a company that provides payroll, benefits, and HR services to small businesses. The role focuses on leading 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, this specific role is not directly building or researching AI models, but rather leveraging AI tools for sales and operational efficiency. The role requires experience in SaaS sales leadership, data analysis, CRM proficiency, and integrating AI into daily workflows for tasks like writing, research, and summarization. | — | 5 |
| Future Opportunities: Retirement Client Relationship Manager This role is for a Client Relationship Manager on the CX team at Gusto, a fintech company focused on small businesses. The role involves managing client relationships, driving retention, resolving complex issues, and collaborating cross-functionally. A key aspect is leveraging AI-assisted tools to improve efficiency and customer service, but the core function is not building or researching AI. | — | 5 |
| Future Opportunities: Retirement Implementation Specialist This role is for a Retirement Implementation Specialist at Gusto, a fintech company. The primary responsibility is managing the end-to-end onboarding and conversion process for 401(k) plans on the Gusto platform. The role involves guiding plan sponsors and administrators, managing a book of business, ensuring accurate data transfer and reconciliation, and partnering with internal teams. While the role is not directly building AI models, it requires active engagement with AI tools to improve efficiency and client communication, indicating an AI-adjacent function within a mature AI-adopting company. | — | 5 |
| Broker Integration Advocate This role is for a Broker Integration Advocate at Gusto, a company that uses AI extensively. The role focuses on managing the customer journey for integrating benefits, ensuring accuracy and timeliness. While the company is AI-native and expects employees to use AI tools, this specific role is customer-facing and process-oriented, not directly building AI models or systems. The primary focus is on customer onboarding and project management within the benefits integration process. | — | 5 |
| Senior Staff Service Designer Senior Staff Service Designer role focused on designing and building AI-assisted service workflows within an enterprise AI context. The role involves creating coherent, resilient, and understandable interactions between AI systems, product experiences, and human teams, with a focus on improving customer experience and operational efficiency. This is a product-focused role that uses AI tools to prototype and improve service delivery. | Agent | 5 |
| Consumer Money Support Specialist, Tier 2 This role is a Tier 2 Consumer Money Support Specialist at Gusto, focusing on complex Wallet and Cash Account issues including fraud, disputes, and account locks. The role requires strong judgment, decision-making, and a focus on member experience within a regulated financial environment. While the role is not directly building AI models, it heavily utilizes AI tools for case research, documentation, and process improvement, indicating a mature adoption of AI within the company's operations. | — | 5 |
| Benefit Services - Member Fulfillment This role is for a Member Fulfillment Specialist at Gusto, a company focused on providing payroll, health insurance, and HR services to small businesses. The specialist will manage the end-to-end enrollment process for health insurance, acting as a liaison between customers and insurance carriers. The role emphasizes accuracy, timeliness, and collaboration, with a strong expectation for all team members to actively use and master AI tools to improve efficiency and accuracy in their daily tasks. While the company is AI-native and expects AI tool usage, the core responsibilities do not involve building or researching AI models themselves, but rather leveraging existing AI tools within an operational context. | — | 5 |
| Senior Staff Software Engineer - Pricing and Packaging Senior Staff Software Engineer and Tech Lead for Gusto's internal Commerce Platform, focusing on architecture and delivery of systems for packaging, pricing, and product delivery. The role involves partnering with product, data science, and engineering teams to build scalable platform infrastructure. The role also emphasizes leveraging AI tools to accelerate engineering velocity and improve team practices. | — | 5 |
| CX Learning & Development Facilitation & Programs Manager This role is for a Learning & Development Manager at Gusto, focusing on people management, facilitation strategy, cohort experiences, and program delivery. The role requires AI fluency, with an emphasis on using AI tools for tasks like copy generation, program design, and analysis, and evaluating AI-enabled learning solutions. The candidate should have experience with LLMs, prompt engineering, and AI tools for content creation and data analysis. | — | 5 |
| Staff Software Engineer, Developer Productivity Async Staff Software Engineer focused on Developer Productivity, enhancing tools and systems for product engineers, with a focus on asynchronous processing using Sidekiq and Kafka. The role involves utilizing AI tools for large-scale code migrations and LLMs to reduce incident resolution time. | — | 5 |
| Jr. Onboarding Associate This role is for a Jr. Onboarding Associate at Gusto, a company focused on providing payroll, benefits, and HR services to small businesses. The role involves interacting with customers via email, chat, and phone to help them choose Gusto, match offerings to their needs, and guide them through the onboarding process. A key aspect of the role is the daily use of AI-powered workflows for sales, research, prep, and summarization, with an expectation to provide feedback for tool improvement. While AI is integrated into the workflow, the core function is customer interaction and sales, not building AI models. | — | 5 |
| Group Operations Fulfillment, Benefit Services This role is for a Group Operations Fulfillment Specialist at Gusto, an AI-native company. The primary responsibility is to manage the end-to-end enrollment process for group health insurance, acting as a liaison between customers and health insurance carriers. The role involves ensuring accuracy and timeliness of all documentation, processing orders, and collaborating with internal and external teams. While the company is AI-native and expects employees to leverage AI tools, this specific role focuses on operational fulfillment and administrative tasks rather than building or researching AI models. | — | 5 |
| Future Opportunities: HR Constultant This role is for an HR Consultant at Gusto, a company that provides payroll, benefits, and HR services to small businesses. The consultant will drive people operations for clients, leveraging technology and systems to improve efficiency. While AI is fundamental to Gusto's operations and employees are expected to engage with AI tools, this specific role is not focused on building or developing AI models. | — | 5 |
| Future Opportunities: Dedicated Service Advisor This role is for a Dedicated Service Advisor at Gusto, a company that provides payroll, benefits, and HR services to small businesses. The advisor will be the main point of contact for customer support, acting as a product expert, educating customers, and advocating for them to influence product decisions. The role involves resolving customer issues, identifying churn risks, and collaborating cross-functionally. A key aspect is the expectation for all team members to actively engage with AI tools relevant to their role and demonstrate AI fluency for efficiency and quality gains. | — | 5 |
| Future Opportunities: Dedicated Service Advisor This role is for a Dedicated Service Advisor at Gusto, a company that provides payroll, benefits, and HR services for small businesses. The advisor will be the main point of contact for customer support, acting as a product expert and customer advocate. The role involves building trust, resolving issues, identifying churn risks, and collaborating cross-functionally. While the company emphasizes AI as fundamental to its operations and expects employees to use AI tools, this specific role focuses on customer service and product support, not direct AI/ML development. | — | 5 |
| Senior Pricing and Monetization Manager This role is for a Senior Pricing and Monetization Manager at Gusto, a fintech company. The role focuses on developing and executing pricing and monetization strategies for Gusto's platform, including payroll, time management, HR, and financial services. While the company emphasizes an 'AI-native environment' and expects employees to use AI tools, the core responsibilities are product strategy, commercial go-to-market initiatives, and KPI management, rather than direct AI/ML model development. The role involves collaborating with various teams and shipping MVPs and pilots, indicating a focus on product delivery within an AI-enhanced workflow. | — | 5 |
| Senior Staff Security Engineer - Network Security Senior Staff Security Engineer focused on network security and edge defense, leveraging AI-native tools and workflows to enhance security operations and automation. | — | 5 |
| Principal Product Manager, Reporting Product Manager for Gusto's Reporting team, focusing on delivering AI-native reporting capabilities to small businesses. This role involves driving strategy, defining vision, shipping customer-facing value, and partnering with engineering, design, and data teams to build AI-powered reporting experiences. | Ship | 5 |
| Partner Account Executive This role is for a Partner Account Executive at Gusto, focusing on the GustoPro platform for accounting firms. The primary responsibility is to recruit, enable, and drive new accounting firm partners to add net new clients. The role involves engaging with C-level executives, negotiating agreements, managing a 30-day enablement plan, and ensuring partners reach activation benchmarks. The role is described as a 'builder' who designs systems and processes, and is expected to leverage AI tools to enhance sales workflows and partner engagement. While AI tools are mentioned as a part of the role's function, the core craft is sales and partner management, not building AI models. | — | 5 |
| Expansion Account Executive This role is for an Expansion Sales Account Executive at Gusto, a company that provides payroll, benefits, and HR services for small businesses. The role involves driving expansion revenue by engaging existing customers through inbound and outbound outreach, using a structured cadence to generate ARR growth. A key aspect of the role is the mandatory use of AI-powered workflows for selling, including running assigned tools daily, identifying inefficiencies, and providing feedback to improve these tools. The role requires 3+ years of consultative sales experience, proficiency in Salesforce, and a proven track record of integrating AI into daily work for writing, research, prep, and summarization, with a focus on providing feedback for tool improvement. | — | 5 |
| Staff Business Systems Analyst This role is for a Staff Business Systems Analyst on the Unified Service Platform (USP) product team at Gusto. The USP team is responsible for engineering the intelligent, AI-driven ecosystem that brings GTM and Service operations into alignment. The role involves driving platform excellence, leading cross-functional delivery, owning the integration ecosystem, acting as a technology strategist, building exceptional Gustie experiences, owning lead-to-cash capabilities, and championing change communication. The ideal candidate has extensive experience with Salesforce, GTM tools, and is comfortable using AI tools to accelerate development. While the role is within an AI-native team and requires using AI tools, the core responsibilities are focused on business systems analysis and platform management rather than direct AI/ML model development. | — | 5 |
| Senior Product Manager, Web Experiences Product Manager for Gusto's website, focusing on the new customer experience and scalability. The role involves owning the website roadmap, balancing improvements to the signed-out customer experience, and ensuring long-term scalability and ecosystem health. The role emphasizes using AI and automation in product development and requires experience with cross-functional collaboration and data-informed decision-making. | — | 5 |
| Head of Customer Referral & Emerging Channels This role leads customer referral and emerging acquisition channels, leveraging AI to identify advocates, personalize outreach, and analyze signals. The primary focus is on building and scaling acquisition programs, with AI used as a tool to enhance these efforts. | Agent | 5 |
| Revenue Operations Analyst This role focuses on leveraging AI tools for data analysis, reporting, and automation within a revenue operations context. The primary goal is to provide insights and support for sales and marketing functions, using AI to enhance data quality, standardize processes, and prototype solutions. While AI tools are integral to the daily workflow, the role itself is not about building or researching AI models, but rather about applying existing AI capabilities to improve business operations and decision-making. | — | 5 |
| Summer Opportunities - Retirement Sales AE This role is for a Mid-Level Retirement Account Executive at Gusto, focusing on selling and expanding 401(k) and retirement plans to small and mid-sized businesses. The role involves consultative sales, managing inbound and outbound opportunities, and guiding customers through the sales process using AI-enabled tools. It requires quota ownership and collaboration with internal teams for plan migration and compliance. | — | 5 |
| Controller, Symmetry This role is for a Controller at Symmetry, a payroll infrastructure company that is part of Gusto. The role involves managing financial close, reporting, accounting for internally developed software and cloud computing arrangements, SaaS revenue recognition, and compliance. A key aspect of the role is to champion and pilot AI and automation tools to modernize finance workflows and improve efficiency. While the company uses AI extensively and expects employees to engage with AI tools, the core function of the Controller is not to build or research AI models, but to leverage AI for operational improvements within finance. | — | 5 |
| Staff Software Engineer, Payments / Risk Staff Software Engineer for Gusto's Payments or Risk platforms. This role involves designing, building, and testing core money movement or risk platform services, mentoring engineers, and collaborating with cross-functional teams. The role requires experience in full-stack development, scaling platforms, and leveraging AI tools to accelerate development and deliver new capabilities. The primary focus is on engineering the core business engine and enabling product teams with reliable backend services. | — | 5 |
| Senior Product Manager, Gusto Pro Workflows Senior Product Manager for Gusto Pro Workflows, focusing on the accountant user base. The role involves leading product discovery, strategy, and iterative development, with a strong emphasis on leveraging AI tools to enhance workflows and deliver customer value. The product manager will partner with engineering, design, and data science, define key metrics, and drive product outcomes in an AI-first environment. | — | 5 |
| Principal Product Operations Manager, Benefits This role focuses on operationalizing and improving AI tools and AI-assisted workflows within a product operations context, specifically for a new Gusto product. The individual will leverage customer feedback and operational metrics, using AI tools to accelerate service design, insight synthesis, and build AI agents for operational tasks. The goal is to enhance customer experience and drive business insights through AI. | Agent | 5 |
| Head of PEO Sales Gusto is seeking a founder-minded sales leader to establish and build their PEO sales organization from the ground up. This player-coach role involves designing the sales motion, building the team, carrying a personal book of business, and leveraging AI tools to drive sales performance and adoption. The ideal candidate has PEO sales expertise and experience building sales teams in a high-growth environment. | — | 5 |
| Future Opportunities: Retirement Advocate This role is for a customer experience professional focused on retirement benefits at Gusto. While the role utilizes AI-assisted tools, the core function is customer support and relationship management within the fintech domain, not direct AI/ML development. | — | 5 |
| Staff Product Designer, Retirement Gusto is seeking a Staff Product Designer for their Retirement team. This role involves shaping strategy, aligning teams, and designing a high-trust retirement experience. The designer will lead the design process, focusing on improving setup, account management, and the connection between payroll and retirement. A key aspect of the role is leveraging AI in daily workflows for faster prototyping and learning, and identifying opportunities where AI can enhance the customer experience. The role also involves translating regulatory requirements into clear UI patterns and mentoring design peers. | — | 5 |
| Benefits Engineering Manager Engineering Manager to lead the design, development, and deployment of AI-powered applications to enhance customer and advocate experiences. This role involves leading a team, mentoring engineers, and leveraging AI/agentic tools to accelerate delivery, with a focus on integrating AI into legacy systems to improve customer interactions. | Ship | 5 |
| Staff Software Engineer, Core Platforms Staff Software Engineer, Core Platforms at Gusto. This role focuses on building and scaling foundational product platforms, including services for communications, reporting, dashboards, access, workflows, risk, payments, and compliance. The engineer will mentor others, collaborate with cross-functional teams, and own the performance of platform services. While not directly building AI models, the role requires leveraging AI tools to accelerate development, improve testing, and deliver new capabilities, with an emphasis on curiosity and safe experimentation with emerging AI frameworks. | — | 5 |