Retirement Implementation Specialist (Conversion Plans)

About this role

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 retirement implementation specialists who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in Fall 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:

The Conversion Specialist manages the onboarding experience for 401(k) plans transferring an existing plan to the Gusto 401k platform. This role oversees the full conversion lifecycle, from initial handoff through asset transfer, data reconciliation, and first contribution, ensuring accurate record keeping and a smooth transition for plan sponsors and administrators. The ideal candidate brings a strong understanding of retirement plan mechanics, meticulous attention to detail, and the confidence to guide employers through a complex, multi-step process. They work exclusively with plan sponsors and administrators and partner closely with Legal, Sales, and Operations to keep conversions on track and compliant.

About the Team:

The Conversion Onboarding team handles one of the most operationally complex moments in a client's journey: moving an existing retirement plan to a new provider. We combine operational rigor with a client-first approach, ensuring sponsors and administrators feel supported and informed at every step — and that assets are transferred accurately and on time.

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

• Manage a dedicated book of business of 401(k) plan conversions from signing through completed asset transfer and first contribution

• Work with plan sponsors and administrators to gather required documentation and ensure accurate data is submitted to support a smooth asset transfer and recordkeeping transition

• Serve as the primary point of contact for plan sponsors and administrators via email, phone, and video, including inbound scheduling through Calendly

• Guide employers through pre-ready task dashboards, proactively preventing stalls and keeping plans on track for their plan start date

• Monitor and drive performance against key benchmarks including time to activation, time to ready, CSAT, and average response time

• Partner closely with Operations and cross-functional teams including Sales and Legal to support asset transfers, client expectations, and complex plan changes

• Use AI tools to streamline workflows, improve client communications, and increase efficiency across your book of business

Here's what we're looking for

• 4+ years of total work experience with 3+ years in client-facing implementation, technical account management, or retirement plan administration; startup and/or financial services experience a plus

• Proven ability to manage a large, active book of business involving complex, multi-step processes simultaneously

• Deep knowledge in one or more of the following: SaaS, Operations, or Finance; retirement plan experience strongly preferred

• Strong analytical skills and meticulous attention to detail, particularly around data accuracy and reconciliation

• Proficiency with Salesforce and comfort working across case management and collaboration tools in a fast-paced environment

• Strong communication skills across email, phone, and video with a client-first mindset

• RPS or CRPS designation a plus, or active pursuit of either; familiarity with ERISA requirements, payroll systems, bundled vs. unbundled providers, or Safe Harbor compliance is a plus

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 histori

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