Retirement Onboarding Specialist (New Plans)

 

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.

About the Role:

The Onboarding Specialist manages the end-to-end onboarding experience for new enterprise 401(k) plans on the Gusto 401(k) platform. This role becomes the dedicated point of contact for plan sponsors and administrators after a new plan signs, guiding them through setup and ensuring first contributions are processed successfully. The ideal candidate is proactive, organized, and experienced in client-facing implementation — comfortable managing a high-volume book of business while keeping employers on track to meet their plan start date. 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 New Onboarding team is the first team a client experiences on their journey with Gusto 401(k). We design a seamless implementation process for a complex employee benefit, instilling trust and transparency from day one and laying the foundation for long-term client success. Our goal is to make plan sponsors feel confident and supported from the moment they sign.

Here’s what you’ll do day-to-day:

• Manage a dedicated book of business of new enterprise and starter 401(k) plans from signing through activation, ensuring timely plan setup 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 activation, time to ready, CSAT, and average response time

• Partner cross-functionally with Sales, Operations, and Legal to resolve setup 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 to provide accurate, confident guidance to employers

• 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, or technical onboarding; startup and/or financial services experience a plus

• Proven ability to manage a large, active book of business while staying organized and proactive across competing priorities

• Deep knowledge in one or more of the following: SaaS, Operations, or Finance; familiarity with 401(k) plans or retirement plan administration is a plus

• 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; familiarity with ERISA requirements and payroll systems a plus

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