Summer Opportunities - Retirement Sales AE

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. Mid-Level Retirement Account Executive (401k Sales) 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. Key Responsibilities Inbound & Targeted Outbound Retirement Sales Motion • 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 Consultative Retirement Engagement • 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 Competitive Plan Migration & Switcher Management • 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 Pipeline Management & Sales Execution • 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 Market Insight & Customer Feedback • 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 Quota Ownership & Performance Accountability • 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 Continuous Improvement & Team Contribution • 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 Here’s What We’re Looking For • 2-4 years of quota-carrying sales experience as an Account Executive, Account Manager, or similar role • Prior experience with outbound prospecting, including calls and email-based outreach • Experience in SaaS, benefits, fintech, or financial services preferred • Interest in or exposure to 401(k), retirement, or benefits sales is a plus • Familiarity with Salesforce CRM and sales engagement tools • Strong communication, organization, and time-management skills • Learner's mindset with a deep commitment to continued growth and development Motivation to thrive in a fast-paced, metrics-driven role while helping small businesses support their employees’ financial futures At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe