Vestwell is the financial technology company powering the new savings economy. The New York City-based fintech platform redefines how people save for the critical aspects of life across retirement, education, and healthcare savings needs. Today, Vestwell enables over 790,000 businesses and more than 2.75 million active savers, with over $57 billion in assets saved across all 50 United States.

Vestwell offers a range of products, including workplace-delivered retirement plans, employer-offered student loan repayment benefits, and various savings accounts for education, emergencies, and individuals with disabilities.

Vestwell's platform serves a diverse clientele, including financial advisers, employers, third-party administrators, financial institutions, payroll providers, government agencies, and individual savers. To learn more, visit vestwell.com

Who Are We Looking For?

We’re growing our Employer Service team and adding a Training Manager to own the full training ecosystem for the specialists who serve 401(k) plan sponsors, HR and payroll administrators, and partners such as TPAs and advisers. You’re a proactive, organized leader and skilled facilitator who can turn complex retirement plan concepts into clear, practical learning that gets new hires productive quickly and keeps the whole team sharp as our products and regulations evolve.

This role partners closely with Employer Service leadership, Plan Onboarding, Operations, Compliance, and product teams to make sure our team is confident, knowledgeable, and ready to deliver an excellent employer experience.

What Will You Be Doing?

Day-to-Day, You Will Be Expected To:

Lead New-Hire Onboarding

Own the new-hire training program for Employer Service specialists, from day one through full proficiency.
Deliver engaging instructor-led, virtual, and hands-on training sessions.
Design nesting and shadowing plans that move new hires from classroom to live work with confidence.
Assess readiness through knowledge checks and practical exercises before new hires take on full workloads.

Build Curriculum & Content

Develop training on 401(k) plan fundamentals, including eligibility, vesting, contributions and match, loans, distributions, and payroll integration.
Create training on employer-facing workflows such as plan onboarding, payroll file issues, plan feature changes, and partner support.
Build and maintain training materials, procedures, job aids, knowledge-base articles, and learning paths.
Keep all content accurate, current, and aligned with company policy and applicable ERISA, DOL, and IRS requirements.

Drive Ongoing Development

Deliver refresher training for new processes, product releases, plan design changes, and regulatory updates (e.g., SECURE 2.0 provisions).
Build advanced and specialized learning paths that support career growth and cross-training.
Run a training calendar that balances team development with service-level needs.

Measure Training Effectiveness

Track training completion, assessment results, time to proficiency**, [e.g., against a target of X weeks]**, and post-training performance.
Gather feedback from learners and leaders to continuously improve content and delivery.
Report on training impact to leadership and recommend improvements.
Use performance and quality trends shared by supervisors to identify where targeted training is needed.

Partner Across the Organization

Collaborate with supervisors and managers to understand skill gaps and team needs.
Partner with product and engineering to prepare the team ahead of new feature and system releases.
Work with Compliance to ensure required regulatory and data-security training is delivered and documented.
Uphold strict confidentiality and data-protection standards in all training materials and examples.

Requirements

The Necessities

5+ years of experience leading training or learning and development in a retirement plan, recordkeeping, financial services, or client service environment
Working knowledge of 401(k) plan administration, including contributions, loans, distributions, and payroll processing