Retirement Implementation Specialist

Retirement Implementation Specialist

San Francisco, CA - Hybrid; Denver, CO - Hybrid; New York, NY - Hybrid; United States - Remote

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.

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 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 Implementation Specialist manages the end-to-end onboarding experience for 401(k) plans on the Gusto platform, spanning both new plan implementations and conversions from existing retirement plan providers. Depending on team assignment, this role guides plan sponsors and administrators through either a new plan setup or a full conversion lifecycle (from initial handoff through asset transfer, data reconciliation, and first contribution). The ideal candidate is proactive, organized, and experienced in client-facing implementation comfortable managing a high-volume book of business, maintaining meticulous attention to detail, and confidently guiding employers through complex, multi-step processes. They work exclusively with plan sponsors and administrators and bring both operational rigor and a client-first mindset to every interaction.

About the Team:

The Retirement Onboarding team oversees two of the most consequential moments in a client's journey with Gusto 401(k): launching a brand-new plan and transitioning an existing one to a new provider. The New Plans pod designs a seamless implementation experience from day one, instilling trust and laying the foundation for long-term client success. The Conversion pod handles operationally complex asset transfers with precision, ensuring sponsors and administrators feel supported at every step and that assets move accurately and on time. Across both, we combine operational excellence with a client-first approach.

Here's What You'll Do Day-to-Day

• Manage a dedicated book of business of 401(k) plans new enterprise/starter plans, conversion plans, or both from signing through activation, asset transfer, and first contribution processing
• 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 following up to prevent stalls and keep plans on track for their plan start date
• Monitor and drive performance against key benchmarks including time to activate, time to ready, CSAT, and average response time
• For conversion plans: gather required documentation, support accurate data submission, and partner with Operations to ensure smooth asset transfers and recordkeeping transitions
• Partner cross-functionally with Sales, Operations, and Legal to resolve setup and compliance issues and align on client expectations
• Surface client feedback to product and leadership to inform platform improvements, and stay current on 401(k) regulations and best practices
• 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, account management, technical onboarding, 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 while staying organized and proactive across competing priorities
• Deep knowledge in one or more of the following: SaaS, Operations, or Finance; retirement plan experience strongly preferred; familiarity with 401(k) plans, ERISA requirements, payroll systems, bundled vs. unbundled providers, or Safe Harbor compliance is a plus
• 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
• Ability to identify and escalate potential setup or compliance issues early, partnering with the right internal teams to resolve them
• RPS or CRPS designation a plus, or active pursuit of either