Gusto

Sales Operations Manager

• Build, automate, and maintain sales performance, funnel, pipeline, SLA, and rep productivity reports and dashboards
• Produce operational reporting, revenue insights, and forecasting models with RevOps, Finance, Marketing, and Analytics
• Own metric definitions and data accuracy
• Identify and prototype AI and automation tools for sales
• Embed AI into daily sales workflows with Sales, BizTech, Product, and Enablement
• Lead AI and automation projects to improve rep productivity
• Identify workflow bottlenecks and implement process improvements
• Document processes, build playbooks, and drive adoption of tools and workflows
• Support HI Sales leadership and representatives with data requests, process issues, and investigations
• Manage account and territory administration, assignments, coverage, reassignments, rerouting, and segment reclassification
• Support territory, quota, coverage planning, and monthly sales-compensation reconciliation
• Troubleshoot reporting issues, broken workflows, missing CRM data, and pipeline visibility gaps
• Partner with Sales Leadership, RevOps, Finance, BizTech, and Product
• Translate sales challenges into business requirements and durable solutions
• Provide updates to managers and senior leadership on timelines, risks, and outcomes
• Advise on complex or ambiguous problems

Health Insurance Sales Operations Analyst

Sales

• Support small and mid-sized businesses with adopting, expanding, and converting 401(k) and retirement plans
• Act as a consultative retirement advisor through inbound opportunities and targeted outbound outreach
• Lead structured, compliant sales conversations and guide customers toward closure using defined workflows and AI-enabled tools
• Manage consultative inbound retirement opportunities and targeted outbound outreach into high-propensity customer segments
• Execute structured, insight-led outbound motions tailored to company maturity, payroll signals, benefits footprint, and prior engagement history
• Own high-volume SMB retirement sales cycles from discovery through close, including moderately complex mid-size customer deals
• Own the end-to-end sales process through plan adoption and Plan Sponsor authorization
• Use AI-powered tools to prioritize opportunities, personalize follow-ups, and reduce administrative work
• Conduct daily consultative retirement conversations about hiring, retention, tax strategy, and compliance
• Educate customers on 401(k) basics, plan design, pricing, employer match considerations, and conversion timelines
• Articulate the value of Gusto’s retirement solution
• Support customers migrating existing 401(k) plans from external providers to Gusto
• Review plan documentation, contracts, and service agreements
• Collaborate with Legal, Compliance, and Retirement Operations on compliant switcher strategies
• Guide customers through the end-to-end plan switcher process and ensure seamless transitions
• Maintain the retirement sales pipeline in Salesforce with accurate notes, opportunity updates, and follow-up tasks
• Keep pipeline stages and close dates updated to support forecasting accuracy
• Partner with Retirement Product, Marketing, Operations, and Compliance on deal handoff and onboarding
• Capture customer questions, objections, and competitive insights
• Share feedback with leadership and cross-functional partners
• Own and work toward a monthly ARR quota
• Participate in daily team huddles and 1:1s
• Seek coaching and apply feedback to improve discovery, objection handling, and close rates
• Share learnings, talk tracks, and wins with the team

Retirement Sales AE

Full-stack Engineer

• Design, build, and test the Gusto PEO Benefits experience, including benefits shopping and plan-recommendation flows, carrier integrations, MCP tools, and agents that automate operational and customer support processes
• Mentor engineers solving complex technical problems in complex domains and at large scale
• Help scale Gusto's Ruby/Rails and JavaScript/React applications
• Collaborate with Product Management, Data, Design, and Platform Engineering teams to understand customer pain points and develop solutions
• Prototype, iterate, and launch product improvements daily
• Shape features from early specification and design through launch and long-term iteration
• Write frontend code and design and build reliable backend APIs
• Influence product direction and own post-launch outcomes
• Build products customers value

Staff Software Engineer – PEO Benefits

Manager

• Own the end-to-end enablement strategy for Gusto's channel partner ecosystem
• Design and deliver partner onboarding, continuous education, certification programs, and just-in-time resources
• Define partner enablement methodology, frameworks, principles, and standards
• Build, adapt, and improve existing enablement programs
• Advise senior leadership on enablement investment, program design, and partner activation conditions
• Own accountability for partner-sourced revenue, activation rates, and program ROI
• Use performance data to influence channel partner strategy and GTM prioritization
• Drive cross-functional alignment across Revenue, Revenue Operations, Product, and Marketing
• Design learner-centered education programs and certification tracks for professional partners
• Monitor industry, regulatory, and competitive trends and translate them into enablement strategies
• Research and apply emerging AI tools and methodologies to scale program design, development, and delivery
• Help define Gusto's perspective on AI in partner enablement

Enablement Manager, Partners

Platform Engineer

• Design, build, and test the platform supporting tax compliance for millions of people
• Help scale Gusto’s Ruby/Rails and TypeScript/React applications
• Collaborate on complex and ambiguous problems with Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross-functional teams
• Improve team productivity and happiness through services, tools, and APIs
• Build guardrails into the Tax platform for safe, compliant, accurate, stable, and reliable agentic AI usage
• Own and drive technical strategy and roadmap for the team’s domain in alignment with team and group-level OKRs
• Identify and prioritize long-term investments in foundational systems and architecture
• Lead improvements to incident response processes, tooling, and culture
• Mentor and develop engineers through pairing, code review, and knowledge sharing
• Guide projects end-to-end, from feature specifications through execution and code maintenance

Senior Staff Engineer – Tax Platform Engineering

• Serve as a Technical Lead across multiple pods in the Money Group, setting architectural direction, unblocking engineers, and ensuring high-quality delivery
• Define the technical vision for domain areas and own shorter-term projects that advance it
• Contribute to architecture connecting Gusto's People Stack and Finance Stack
• Lead migration from a large Ruby-on-Rails monolith to a service-oriented architecture
• Define domain boundaries across money movement, lending, and tax
• Manage partner ecosystem and lead technical due diligence in vendor evaluation
• Build prototypes and proof-of-concepts to de-risk ideas and unblock product decisions
• Partner with Product Management, Design, Data Science, Compliance, and Operations on complex problems
• Drive AI-native architecture decisions for transaction categorization, tax optimization, and conversational financial management
• Provide technical consulting to teams and partner teams
• Set standards for technical excellence through code and design reviews
• Mentor engineers and help build healthy, high-performing teams

Senior Staff Software Engineer, Money Group

Human Resources

• Serve as a trusted advisor and strategic partner to frontline managers and skip-levels
• Navigate complex, high-stakes employee matters with sound judgment and care
• Manage employee concerns and workplace conflict resolution through investigations, disciplinary action plans, and mediated conversations
• Coach and support managers on performance expectations, feedback, development needs, performance management plans, and offboarding
• Maintain current knowledge of HR regulations and ensure adherence to Gusto policies and legal requirements
• Partner with Legal and People Partners to assess organizational risk and determine actions on escalated cases
• Balance employee experience with business and legal risk in ambiguous situations
• Maintain thorough and legally defensible documentation across ER cases
• Identify case patterns and surface systemic risks to People leadership
• Provide a connection between the business and People Team within the shared services model

Employee Relations Partner

Operations

• Own the operational layer of specific payment workflows, including ACH processing, exception handling, refunds, collection re-debits, and reconciliation
• Investigate payment issues, escalate when needed, drive resolution, and address root causes
• Contribute to product specifications, surface operational pain points, define requirements, and participate in launches with Product and Engineering
• Mine customer and CX feedback to identify friction in payment flows and prioritize improvements
• Connect payment rails, partners, reconciliation, compliance, and customer experience impacts
• Work directly with domestic and international bank and payment partners to triage issues and resolve escalations
• Use AI to accelerate analysis, draft communications, synthesize data, and automate repetitive work

Payment Operations Analyst

• Lead, hire, coach, and develop a team of Payment Operations Analysts
• Set expectations, provide feedback, and own team-level SLAs, on-call rotation, escalation paths, reporting, and team output
• Use data to identify process breakdowns and fix root causes
• Own operational relationships with banking and payment partners, including issue triage, escalations, operational reviews, renewals, and due diligence
• Personally work tickets when queues back up or SLAs are at risk
• Execute day-to-day work for Nacha, unclaimed property, bank compliance, and Payment Ops SOC 1 audit programs
• Maintain compliance documentation, controls, and evidence and coordinate with compliance and GRC teams
• Investigate payment incidents such as failed batches, reconciliation breaks, and partner outages
• Keep stakeholders informed and lead retrospectives to prevent recurrence
• Partner with Product and Engineering on payment-related specifications, risks, and operational needs
• Model and encourage AI use for investigation, documentation, and automation

Payment Operations Manager

Customer Support

• Own the end-to-end new customer experience, including natively incorporating AI to assist customers
• Set and evangelize strategy for how small businesses discover, evaluate, and start using Gusto, including AI assistants and agentic surfaces
• Create a best-in-class new customer experience that increases acquisition volume and optimizes onboarding conversion
• Establish Gusto as the default small business partner solution
• Collaborate with Engineering, Design, Data, Marketing, Sales, and Finance
• Rally cross-functional teams and leaders around a shared onboarding platform strategy
• Directly coach and lead a team of senior product managers
• Raise the bar on product craft, customer understanding, and execution velocity

Head of Product, New Customer Experience

• Architect and evolve customer-facing web platforms with a focus on scale and performance
• Build innovative AI interfaces to assist customers
• Design, build, and maintain shared services enabling rapid iteration on product offerings
• Implement and optimize key workflows for a best-in-class customer experience
• Write high-quality, well-tested code across the stack using AI-powered tools
• Support, mentor, and up-level fellow engineers
• Establish best practices for AI-native design patterns
• Partner with Marketing, Sales, Operations, and leadership to translate business needs into technical solutions
• Influence the technical roadmap for the Benefits Advisory platform
• Build capabilities enabling customers to explore, apply for, and maintain benefits
• Transform benefits opportunity, shopping, and renewal flows
• Design scalable services and enable AI-driven benefits-shopping interfaces

Senior Staff Software Engineer, Benefits

• Own full-stack features independently from technical design through implementation, testing, and production monitoring
• Design, build, and maintain features for the HRX Engineering product surface
• Write clean, well-tested, maintainable code across the stack
• Participate in code review, sprint planning, and retrospectives
• Partner with product and design to translate requirements into technical solutions
• Monitor and improve the reliability, performance, and quality of shipped features
• Participate in on-call rotation and lead incident response for owned systems
• Provide technical guidance and code-review mentorship to less-tenured engineers

Staff Software Engineer, HR Experience

• Function as a Technical Lead across multiple teams in Payroll Services, keeping engineers unblocked and supporting long-term goals
• Design, build, and test the foundation supporting compliant payroll for millions of people
• Help scale Gusto’s Ruby/Rails and TypeScript/React applications
• Collaborate on complex and ambiguous problems with Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross-functional teams
• Mentor and grow fellow engineers creating holistic and scalable solutions
• Drive product development from concept to launch for payroll, tax, and compliance products
• Improve team productivity and happiness through services, tools, and APIs
• Work in a supportive environment to drive productivity and innovation
• Stay current with AI and Machine Learning advancements and apply this knowledge to projects

Principal Software Engineer – Pay Group Engineering

Product Manager

• Lead long-term product strategy through research, customer and market positioning, product direction, and identification of required investments and capabilities
• Translate strategy into actionable guidance for company-wide planning and execution
• Identify highest-leverage investments and decisions to build a market-winning payroll tax offering
• Partner with Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations
• Uncover insights, validate assumptions, build alignment, and create shared context
• Clarify requirements, initiate strategic initiatives, and embed with teams to drive execution
• Own development of new payroll tax business lines and 0-to-1 products
• Lead discovery, strategy, and execution for new AI-powered payroll tax products
• Deliver new revenue and retain existing revenue

Senior Product Manager, New Tax Products

Compliance

• Serve as the ERISA/compliance escalation point for Conversion Ops and Sales on complex plan provisions, eligibility questions, and Adoption Agreement interpretation
• Own end-to-end quality assurance for the plan review process, validating each build against the signed Adoption Agreement and developing internal tooling and business rules to support review at scale
• Conduct plan reviews for new and converting 401(k) plans, translating complex legal plan documents into clear, accurate guidance for internal teams and customers
• Build and deliver internal training and reference materials for Conversion Ops, Sales, and Customer Experience teams
• Partner with Legal & Compliance on regulatory interpretation and sign-off for higher-risk plan changes
• Identify and champion opportunities to use AI tools and automation to reduce manual review time while strengthening accuracy across plan setup and compliance workflows
• Serve as a subject-matter expert on ERISA compliance and 401(k) plan administration
• Provide independent quality assurance, training, complex corrections, and consultation on ambiguous or high-risk plan provisions
• Work closely with Conversion Ops, Sales, and Legal & Compliance
• Help shape tools and processes used by the broader organization