Summer Opportunities - Retirement Sales AE

About the role

Gusto is dedicated to growing the small business economy. We handle essential tasks like payroll, health insurance, 401(k)s, and HR, allowing business owners to focus on their craft and customers. Our teams are located in Denver, San Francisco, and New York, serving over 500,000 small businesses nationwide. Full-time employees receive competitive compensation, benefits, and equity.

Responsibilities

• 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.
• Seek coaching and apply feedback to improve discovery, objection handling, and close rates.
• Contribute to team success by sharing learnings, talk tracks, and wins.

Requirements

• 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.

Qualifications

• Education: Bachelor’s degree preferred.
• Experience: 2-4 years of quota-carrying sales experience as an Account Executive, Account Manager, or similar role.
• Technical Skills: Familiarity with Salesforce CRM and sales engagement tools.
• Soft Skills: Strong communication, organization, and time-management skills.
• Industry Knowledge: Experience in SaaS, benefits, fintech, or financial services preferred.

Skills

• Outbound Sales: Ability to manage consultative inbound retirement opportunities and targeted outbound outreach.
• Customer Engagement: Proficiency in conducting daily consultative retirement conversations to understand customer goals.
• Product Knowledge: Understanding of 401(k) basics, plan design options, pricing, employer match considerations, and conversion timelines.
• Compliance: Ability to collaborate with Gusto’s Legal, Compliance, and Retirement Operations teams to design a compliant switcher strategy.
• Technology: Familiarity with AI-powered tools to prioritize opportunities, personalize follow-ups, and reduce administrative work.
• Teamwork: Ability to partner with cross-functional teams and contribute to team success.

Benefits

At Gusto, we offer competitive base pay, benefits, and equity to all full-time employees. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

Pay

Competitive base pay is determined by role, level, and location. Learn more about our Total Rewards philosophy.

Schedule

Employees who are based in Gusto’s Denver, San Francisco, or New York City offices will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto’s subsidiary, whose physical office is in Scottsdale. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Equal Opportunity Employer

We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.