Retirement Sales Account Executive (Summer Opportunities)

• As a Mid-Level Retirement Account Executive at Gusto, you will support small and mid-sized businesses by helping them adopt, expand, and convert 401(k) and retirement plans
• In this role, you’ll act as a consultative retirement advisor, engaging customers through a blend of inbound opportunities and targeted outbound outreach into high-propensity accounts within Gusto’s existing customer base
• You’ll lead structured, compliant sales conversations, guide customers through decision steps, and move opportunities toward closure using defined workflows and AI-enabled tools
• This role focuses on high-volume SMB deal cycles, while also supporting slightly more complex mid-sized customers that require deeper discovery and coordination
• You’ll guide business owners through retirement decisions by educating them on plan options, compliance basics, tax advantages, and employee benefits—driving meaningful ARR growth while building strong sales fundamentals
• Manage a mix of consultative inbound retirement opportunities and targeted outbound outreach into high-propensity customer segments
• Execute a structured, insight-led outbound motion into Gusto’s customer base, tailoring outreach based on company maturity, payroll signals, benefits footprint, and prior engagement history
• Own high-volume SMB retirement sales cycles from discovery through close, with exposure to moderately complex mid-size customer deals
• Own the end-to-end sales process for high-propensity SMB accounts, from initial discovery of retirement needs to final plan adoption and “Plan Sponsor” authorization
• Leverage AI-powered tools to prioritize opportunities, personalize follow-ups, and reduce administrative work
• Conduct daily consultative retirement conversations to understand customer goals related to hiring, retention, tax strategy, and compliance
• Educate customers on 401(k) basics, plan design options, pricing, employer match considerations, and conversion timelines
• Clearly articulate the value of Gusto’s retirement solution as a simple, modern alternative to legacy providers
• Partner with customers who maintain existing 401(k) plans with external providers and are seeking to migrate to Gusto’s Retirement platform
• Lead discovery to collect and review existing plan documentation, contracts, and service agreements, ensuring a clear understanding of plan structure, pricing, and fiduciary obligations
• Collaborate closely with Gusto’s Legal, Compliance, and Retirement Operations teams to design a compliant switcher strategy that meets regulatory requirements and platform capabilities
• Guide customers through the end-to-end plan switcher process, setting clear expectations, mitigating risk, and ensuring a seamless transition to Gusto’s retirement offering
• Maintain an organized retirement sales pipeline in Salesforce, including accurate call notes, opportunity updates, and follow-up tasks
• Support forecasting accuracy by keeping pipeline stages and close dates up to date
• Partner cross-functionally with Retirement Product, Marketing, Operations, and Compliance to ensure smooth deal handoff and onboarding
• Capture complex customer questions, objections, and competitive insights from daily conversations
• Share feedback with leadership and cross-functional partners to help refine messaging, sales plays, and enablement
• Own and work toward achieving a monthly ARR quota driven by new 401(k) sales, plan switchers, and customer expansion
• Operate with consistency and urgency in a high-activity, high-expectation sales environment
• Participate in daily team huddles and 1:1s to review priorities, pipeline, and skill development areas
• Actively seek coaching and apply feedback to improve discovery, objection handling, and close rates
• Contribute to team success by sharing learnings, talk tracks, and wins

Benefits

• Gender-affirming care and support
• Family care and support, including family planning and fertility benefits
• A variety of mental health resources
• Medical, dental, and vision insurance for employees and dependents
• Free meals and refreshments at the office (conversation and community is an added bonus!)
• Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more

• Prior experience with outbound prospecting, including calls and email-based outreach
• Interest in or exposure to 401(k), retirement, or benefits sales is a plus
• Strong communication, organization, and time-management skills
• Learner’s mindset with a deep commitment to continued growth and development
• 2-4 years of quota-carrying sales experience as an Account Executive, Account Manager, or similar role
• Experience in SaaS, benefits, fintech, or financial services preferred
• Familiarity with Salesforce CRM and sales engagement tools