Jobs at Gusto

Designs, facilitates, and evaluates data-driven learning programs for customer experience teams. Responsibilities include instructional design, AI-enabled training, cohort and program management, stakeholder consultation, learner coaching, communications, and learning analytics. The role owns program outcomes, uses Kirkpatrick Model evaluations and KPIs to optimize learning, and mentors learners and junior team members while partnering with senior leadership.

Own and scale Gusto's VC and PE partnership strategy, building programmatic, high-leverage ecosystem motions. Lead partner portfolio decisions, design repeatable programs with Marketing/Events/Sales, track ARR and pipeline impact, and represent Gusto externally to drive founder and investor engagement.

Lead a team of 10–15 licensed benefits advisors through renewal cycles to drive retention, revenue growth, and exceptional customer experience. Coach for performance, run cross-functional projects to improve processes and tooling, integrate AI responsibly, and ensure compliance. Partner with Product, Sales, and Carrier Ops to optimize advisor workflows and customer outcomes.

Manages end-to-end onboarding for new enterprise and starter 401(k) plans, serving as the primary contact for plan sponsors and administrators. Guides clients through setup, tracks readiness and activation benchmarks, processes first contributions, resolves issues with internal teams, and proactively prevents delays. The role also surfaces client feedback, supports compliance-related questions, and uses AI tools to improve workflows and communications.

Manage a portfolio of high-value customers as their dedicated technical and payroll support advisor. Build trusted relationships, resolve payroll and benefits inquiries, educate customers on products, identify and mitigate churn risk, and advocate for customer needs internally. The role requires cross-functional collaboration, strong product and payroll expertise, effective communication, creative problem-solving, and responsible use of AI-assisted tools while maintaining compliance and data privacy.

Lead the configuration, optimization, and support of Workday HR and payroll solutions across HCM, Payroll, Absence, Time Tracking, Talent, and Compensation. Develop business processes, calculated fields, security roles, reports, dashboards, and testing strategies. Ensure data quality, audit readiness, release management, and system reliability while advising stakeholders, resolving complex issues, mentoring team members, and guiding best practices.

Own and improve Benefits Labs, an AI-powered system for intake, pilot governance, execution, measurement, evidence synthesis, and leadership recommendations. Build agents, automations, and workflows that scale operational change with minimal manual effort. Define success metrics, improve pilot quality, solve systemic process issues, coordinate cross-functional teams, influence decisions through data-driven narratives, coach Pilot Leads, and shape the future operating model for Benefits Labs.

Own inbound customer inquiries via phone (with email/chat flexibility), research complex benefits questions, collaborate cross-functionally to influence product, meet quality/productivity standards, and support peak-season overtime and blackout PTO periods.

Design and lead AI architecture for FP&A planning, forecasting, reporting, and analysis. Build ML-assisted forecasting systems and agentic workflows for variance commentary, scenario modeling, board narratives, and financial queries. Establish governed finance data foundations, auditability, human-in-the-loop controls, and AI evaluations. Evaluate planning and AI tools, partner with Finance, Data, and Engineering, mentor teams, and measure improvements in forecast accuracy, cycle time, analyst capacity, and decision speed.

Leads end-to-end recruiting for design and specialized technology roles, specializing in sourcing senior design talent and advising hiring leaders. Builds talent pipelines, uses data and AI to improve search strategy, delivers high-touch candidate experiences, partners cross-functionally, and supports Product Management, Data, and other technical searches. Also develops San Francisco’s design community through local events and relationship-building.

Resolve payroll tax notices for customers by researching discrepancies and tax laws, communicating with tax agencies, documenting cases, and collaborating with compliance and tax operations teams. Manage a daily queue, meet deadlines, explain complex issues clearly, use AI tools, and provide proactive customer support while identifying process improvements and escalating complex cases when needed.

Build and evolve backend payroll platform services and APIs used by multiple engineering teams. Own a core domain, ensuring correctness, scalability, reliability, performance, and observability. Lead architecture and design decisions, solve ambiguous technical problems independently, and partner with product and engineering teams on platform adoption. Collaborate cross-functionally to deliver compliant payroll capabilities while promoting responsible use of AI-assisted development tools.

Build customer-facing full-stack experiences for recommendations, nurture campaigns, booking flows, and plan upgrades. Design reliable backend APIs and data models, run experiments, improve conversion and retention, mentor engineers, and collaborate with Product, Design, Data, and Platform teams. The role requires ownership of complex, multi-quarter projects, scalable architecture, refactoring, performance, reliability, and responsible use of AI tools.

Own the technical direction and business outcomes of Gusto’s expansion funnel, including recommendations, conversion journeys, experimentation, and retained revenue growth. Partner with Product, Design, and Data Science to shape roadmaps, make scoping decisions, build scalable architecture, and iterate based on data. Provide technical leadership through code reviews, mentoring, delegation, refactoring, and reliability improvements while delivering customer-facing products at scale.

Own full-stack HR Experience features from technical design through deployment and monitoring. Build maintainable frontend, backend, and data-layer solutions; participate in code reviews, planning, reliability improvements, on-call response, and incident management. Partner with product and design, mentor less-tenured engineers, and independently deliver projects with minimal oversight.

Leads Gusto’s internal controls function across business process and IT controls. Builds the team and ICFR strategy, oversees risk assessment, control design, testing, remediation, governance, and external auditor relationships. Partners with Accounting, Finance, Product, Engineering, Data, Security, and Risk to embed scalable controls into complex systems and financial processes. Establishes AI-enabled controls practices and oversight for AI-related risks, while reporting program effectiveness to senior leadership and the Audit Committee.

Own end-to-end product design for Gusto’s Money, Banking, Retirement, or HR Experiences teams. Responsibilities include framing ambiguous problems, shaping product roadmaps, designing accessible and trustworthy AI-enabled experiences, conducting customer research, evolving design systems, and collaborating with product, engineering, and data teams. The role requires strong craft, systems thinking, judgment around AI uncertainty and human handoffs, and experience shipping products in high-trust or regulated domains.

Lead organization-wide technical initiatives for Gusto’s API and AI agent platform. Design reliable, scalable API contracts and agent-facing tools, write clean Ruby on Rails code, mentor engineers, improve reliability and observability, engage developer customers, and troubleshoot production issues.

Own paid social strategy and execution across Meta, LinkedIn, Reddit, Quora, TikTok, and emerging channels. Manage multimillion-dollar budgets, full-funnel campaigns, attribution, forecasting, creative testing, and pipeline performance. Lead AI-powered marketing workflows, evaluate new media channels, and develop acquisition playbooks. Partner with web, brand, engineering, product marketing, sales, communications, and integrated marketing teams to improve tracking, conversion, creative strategy, and revenue outcomes.

Leads Gusto’s commercial insurance servicing team, overseeing licensed account managers, service quality, escalations, carrier relationships, compliance, and performance metrics. The role develops SOPs, improves automation, partners with product and engineering, manages complex Workers’ Compensation servicing issues, coaches staff, and supports hiring and team growth. It requires commercial lines experience, strong Workers’ Compensation knowledge, carrier portal expertise, AI and automation fluency, supervisory compliance capability, and an active Property & Casualty producer license.