Summer Opportunities - Retirement Sales AE

The role

You will support small and mid-sized businesses by helping them adopt, expand, and convert 401(k) and retirement plans. You will act as a consultative retirement advisor using inbound opportunities and targeted outbound outreach.

What you will do

• Manage consultative inbound retirement opportunities and targeted outbound outreach.
• Execute outbound motion into the customer base based on company maturity and payroll signals.
• Own high-volume SMB retirement sales cycles from discovery through close.
• Conduct daily consultative retirement conversations to understand customer goals.
• Educate customers on 401(k) basics, plan design, pricing, and employer match.
• Partner with customers to migrate existing 401(k) plans to Gusto.
• Maintain an organized retirement sales pipeline in Salesforce.
• Support forecasting accuracy by keeping pipeline stages and close dates up to date.
• Capture customer questions, objections, and competitive insights.
• Achieve a monthly ARR quota driven by new sales and plan switchers.

Required qualifications

• 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
• 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

Nice to have

• Experience in SaaS, benefits, fintech, or financial services
• Interest in or exposure to 401(k), retirement, or benefits sales

Benefits

• Competitive base pay
• Benefits
• Equity (RSUs)

Before you apply

• AI experience will be assessed during the interview process

About the company

Gusto handles payroll, health insurance, 401(k)s, and HR to support the small business economy. They have teams in Denver, San Francisco, and New York.