Summer Opportunities - Retirement Sales AE at gusto | AI Job Board

Job description

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

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations 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.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

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.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also 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.

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Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.