Summer Opportunities Retirement Sales AE

About Gusto

At Gusto were 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 500000 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 this role youll act as a consultative retirement advisor engaging customers through a blend of inbound opportunities and targeted outbound outreach into high-propensity accounts within Gustos existing customer base. Youll 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. Youll guide business owners through retirement decisions by educating them on plan options compliance basics tax advantages and employee benefitsdriving 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 Gustos 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 Gustos 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 Gustos 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 Gustos 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 Gustos 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
  
  

Heres What Were 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
• Learners 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 Gustos 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 its 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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