Future Opportunities: Retirement Advocate

Gusto
Chicago, IL
* 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.

Submit your interest to join our CX team!

Gusto is seeking customer experience professionals who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in 2026 . If you’d like to be considered for future opportunities with our team, please complete the form below and upload your resume.

While start dates are still being determined for 2026, we’d love to connect! Does this sound like you? Apply below!

About the Role:

Gusto is seeking motivated, customer-centric professionals interested in being considered for future retirement benefits customer experience opportunities in 2026. These roles are ideal for customer-facing retirement benefits professionals who thrive in a fast-paced, consultative environment and are passionate about helping small businesses succeed.

As a seasoned Retirement Benefits Advocate, you will act as the single point of contact for all support inquiries, enhancing user experience and serving as a subject matter expert for Gusto’s core products. You will serve as a strategic partner, providing a holistic and consultative approach to help clients optimize their retirement plan. Your mission is to empower our clients by proactively educating them on their plan's health, fiduciary responsibilities, and the tools available to drive employee engagement and retirement readiness. You will build deep client loyalty and act as the driver for full resolution of all plan-related matters. You’ll address and solve real problems and deliver an exceptional customer experience to build trust and loyalty to Gusto.

Here’s what you’ll do day-to-day:
  • Own the customer journey by building trust, rapport, and partnership with customers through inbound and outbound phone, email, and Zoom interactions.
  • Provide passionate, opinionated, consistent, expert, reliable support as a point of contact for retirement benefits inquiries.
  • Leverage AI‑assisted tools to accelerate research and communication while upholding accuracy, compliance, and Gusto’s voice.
  • Identify churn risk and quickly act to deliver solutions to mitigate the risk of churn, using your product knowledge and unique understanding of each individual customer.
  • Build and maintain relationships built on trust and collaboration with admins to better understand and anticipate their needs.
  • Partner with your customers and cross-functionally to unblock points of friction, proactively address potential concerns, and build an understanding of individual team needs and processes.
  • Think creatively, pivot quickly, live in ambiguity, and collaborate strategically. You will be required to expand your critical thinking skills and creatively problem-solve across all areas of the business, with an understanding of a variety of stakeholders and needs.
Here’s what we're looking for:
  • 3-6 years of customer experience with 1+ years of full-time experience in retirement benefits.
  • Experience with 401k retirement plans preferred.
  • Account Management experience preferred.
  • Proven ability to proactively and reactively support customers, driving their success, happiness, and loyalty through expert guidance and creative problem-solving.
  • Ability to synthesize and communicate complex subjects clearly and effectively, both verbally and in writing, with customers and internal partners.
  • Experience with Salesforce, Zoom, Google Suite, Google Calendar, Gmail, and Chili Piper.
  • Excels in balancing inbound calls, scheduled meetings, and email inquiries while managing and prioritizing multiple high-priority resolutions effectively.
This posting represents a general talent pipeline that spans multiple levels within our CX team. Final compensation will be determined based on the specific role, level, and experience alignment. The estimated compensation range for these roles is $21.00–$35.00 per hour. *

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 2026-08-09

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