Gusto

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

This role is for a Workplace Operations Lead who will ensure seamless day-to-day workplace operations and deliver a high-touch, hospitality-driven employee experience at the Denver office. The role involves facilities coordination, vendor management, asset tracking, maintenance, workplace request workflows, office services, event support, EH&S program management, and process improvement. The candidate will use AI tools to draft communications, summarize feedback, identify patterns in requests, track open requests, flag overdue items, analyze vendor spend, and leverage AI-driven dashboards for occupancy, safety, and resource usage. The role requires building at least one workflow from scratch using AI.

Senior Staff Security Engineer focused on network security and edge defense, leveraging AI-native tools and workflows to enhance security operations and automation.

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.

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.

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.

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.

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.

Senior Manager, Growth Data Science at Gusto, leading a team to leverage data and AI for product understanding, scaling, and growth. The role involves managing data scientists and analysts, shaping strategy through data, developing measurement frameworks, supporting experimentation (including for AI/ML systems), partnering on AI-powered product development, and influencing senior leadership. Requires 10+ years in data science with 4+ years of management experience, deep product analytics expertise, technical fluency, AI product intuition, strategic acumen, and strong communication skills. Experience with ML applications in product contexts is preferred.

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.

Gusto is seeking a Partner Manager to drive the strategy and growth of their Gusto Pro accounting firm partners. The role involves managing existing revenue, identifying growth opportunities, building relationships, and collaborating with internal teams to influence product roadmap. The ideal candidate will have 5+ years of experience in a sales-related function, a track record of exceeding sales quotas, deep understanding of the accounting firm landscape, and proven experience integrating AI into their daily workflow for sales, research, and summarization.

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.

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.

This role is for a Senior Paid Social Marketing Lead who will own the paid social program end-to-end, from brand awareness through conversion, across various social channels. The role involves managing multi-million dollar budgets, defining measurement frameworks, leading creative strategy and testing, and acting as an internal subject matter expert on paid social and AI-powered marketing workflows. The ideal candidate will be AI-fluent in practice, using AI tools consistently in their daily workflow to accelerate tasks and implement AI-driven efficiencies.

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.

This role is for a Head of Partner Growth at Gusto, focusing on their Embedded Payroll platform. The primary responsibility is to lead a team that drives go-to-market execution, revenue growth, and operational frameworks for embedded partners. While the role involves leading a team and managing strategic relationships, a significant emphasis is placed on leveraging and driving AI fluency within the team, embedding AI tools into daily operations, and identifying AI-powered workflows to improve efficiency and decision quality. The role is product-focused within the enterprise AI domain, aiming to scale the embedded payroll business.

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.

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.

This role is for a Senior Franchise Account Executive at Gusto, a company that provides payroll, benefits, and HR services for small businesses. The primary focus is on generating new franchise revenue by prospecting, building relationships with multi-unit operators, and closing deals. The role involves executing and refining the franchise sales playbook, managing the full sales cycle, and partnering cross-functionally. A key aspect is the expectation for all team members to actively use and provide feedback on AI tools integrated into their workflows, particularly in sales activities like writing, research, prep, and summarization.

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.

This role is for a licensed Property & Casualty Insurance Broker to pilot a new broker model at Gusto. The individual will quote and issue business insurance policies, provide customer support, and act as a human-in-the-loop to train and optimize an AI insurance advisor. The role requires active engagement with AI tools, sales experience, and insurance licensing.

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.

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.

Staff Software Engineer, Observability at Gusto. This role focuses on shaping observability standards, owning and evolving the observability platform (logging, metrics, tracing), and building AI-native capabilities for anomaly detection, failure diagnosis, and root cause analysis. The role also involves creating developer experiences, driving reliability automation, and partnering with engineering teams. Requires 8+ years of experience in observability/monitoring infrastructure, experience with platforms like Datadog, and proficiency in Ruby, Python, or TypeScript. Experience with cloud infrastructure, IaC, and Kubernetes is preferred.

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.

This role is for a Sr. Sales Compensation Analyst at Gusto, a company that uses AI tools. The analyst will be responsible for end-to-end compensation administration, shaping compensation programs, and driving operational frameworks. They will leverage AI tools to automate tasks, accelerate reporting, and surface insights, contributing to the company's growth.

This role is for a Senior Compensation Partner at Gusto, a company focused on serving small businesses. The role is part of the People team and is responsible for building and scaling compensation programs. It emphasizes a systems-first, AI-aware mindset, using automation and AI tools to improve decision quality, ensure compliance, and reduce manual analysis. The role involves developing, implementing, and communicating compensation programs, leading annual cycles, performing market analyses, using AI tools for analysis and reporting, designing scalable workflows, building dashboards, crafting offers, ensuring regulatory compliance, and optimizing HRIS and compensation tools. The ideal candidate has 8+ years of experience in compensation or a related field, AI fluency, experience running compensation cycles, survey benchmarking expertise, a systems-first orientation, strong analytical skills, knowledge of compensation law, and excellent communication skills.

This role focuses on owning the financial data layer for Gusto's payment platform, ensuring accuracy, completeness, and auditability. It involves designing and implementing AI-powered workflows for reporting, analysis, and controls, with a strong emphasis on data integrity and regulatory compliance within a FinTech environment. The role requires a blend of accounting expertise, data skills (SQL), and a proactive approach to adopting and evaluating AI tools.

Principal Software Engineer for Gusto's Money Group, focusing on technical leadership, architectural vision, and driving AI-native solutions for financial products. This role involves migrating services from a monolith to a service-oriented architecture, managing partner ecosystems, and mentoring engineers, with a strong emphasis on integrating AI for features like transaction categorization and conversational finance.

This Principal Product Manager role focuses on building products related to tax credits for small businesses. While the company emphasizes the use of AI tools in product development and expects employees to engage with them, the core function of the role is product management and strategy for a specific business domain, not the direct development or research of AI models or systems. The role involves leading product discovery, running experiments, and creating long-term vision, with AI being a tool to achieve these goals.

This role is for a Senior Field Event Marketing Manager at Gusto, responsible for designing, producing, and optimizing event marketing programs. The role involves collaborating with cross-functional teams, managing budgets and timelines, building relationships with external partners, and leveraging AI tools to enhance event marketing workflows. The ideal candidate has 7-10 years of experience in event marketing and production, strong project management skills, and AI fluency.

This role is for a Sales Enablement Learning Partner focused on PEO & Business Insurance at Gusto. The primary function is to design and implement learning solutions for sales teams, focusing on product knowledge, skill development, and driving revenue growth. While the role is not directly building AI models, it requires active engagement with AI tools and a focus on leveraging them to improve sales enablement processes. The role emphasizes collaboration, needs analysis, solution design, delivery, and performance measurement, with a strong focus on learner-centered design and continuous improvement.

Senior Product Manager for Gusto's Contractor Products team, focusing on end-to-end contractor management for SMBs. The role involves leading long-term strategy, defining product vision, and driving execution, with an expectation to actively use AI tools in the product development process.

Head of Engineering for Gusto's Money Group, responsible for the end-to-end Money platform and product engineering organization. This role owns the technical vision, architecture, and delivery across Consumer Money, Business Money, Accounting, Expenses & Invoicing, and Payments. The focus is on building secure, scalable, and compliant financial systems, modernizing essential platforms, and driving product innovation including AI-powered automation, while ensuring reliability and operational excellence.

This role is for a Senior Community Marketing Manager focused on the accountant audience. The primary responsibility is to build and scale Gusto's brand presence and community within this group through thought leadership, community programs, events, and partnerships. The goal is to drive firm recruitment, activation, and engagement, strengthening Gusto's reputation. The role involves developing community strategy, representing Gusto externally, creating and scaling community programs, owning thought leadership, and collaborating with various internal teams. Success metrics will include community health, awareness, sentiment, engagement, and funnel performance. The role requires experience in community marketing, program scaling, external representation, and data-informed decision-making. AI fluency is required for using AI tools to improve efficiency in content creation, personalization, and insight generation.

Product leader to own the development of new business lines for payroll tax products, focusing on AI-powered solutions. This 0 to 1 role requires leading discovery, strategy, and execution for new products, with a focus on delivering durable business outcomes.