Sales Development Representative

gusto
Chicago, IL

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy .

About the Role

As a Sales Development Representative (SDR) on the Gusto 401(k) team, you will be the first point of contact for prospective customers exploring retirement benefits. You’ll engage inbound leads, qualify opportunities, and leverage AI-powered tools to work efficiently and thoughtfully. This role is ideal for someone eager to build foundational sales skills in a high-growth, collaborative environment.

About the Team

The Gusto 401(k) Sales team helps small businesses offer meaningful retirement benefits by combining payroll and retirement into one seamless experience. We operate in an AI-native way, using technology to improve productivity, clarity, and customer understanding while maintaining a human-centered sales approach.

Here's what you'll do day-to-day

  • Engage inbound Gusto customers via phone, email, and AI-enhanced communication tools
  • Conduct discovery conversations to understand customer needs and qualify opportunities
  • Use AI to prioritize leads, personalize outreach, and recommend next best actions
  • Partner with Account Executives to ensure high-quality opportunity handoffs
  • Maintain accurate CRM records and leverage AI-driven insights in Salesforce
  • Collaborate with teammates to refine sales strategies and AI best practices

Here's what we're looking for

  • 1–2 years of professional experience (internships included)
  • Experience in customer-facing, sales, or business development roles preferred
  • Strong written and verbal communication skills
  • Comfort learning and using AI tools to improve efficiency and decision-making
  • High ownership mindset with strong organizational skills
  • Ability to collaborate in a supportive, inclusive team environment

Our cash compensation amount for this role is targeted at $66,000 for OTE (90% base and 10% variable bonus) in Denver and most remote locations. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

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.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer .

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

Posted 2025-12-19

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