Training Manager, Employer Services

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.

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

• 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.

• 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.

• 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.

• 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.

• 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.

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
• Strong facilitation and presentation skills, both in person and virtually
• Experience designing training content; familiarity with instructional design and LMS tools is a plus
• Ability to manage multiple priorities in a fast-paced environment
• Working familiarity with ERISA and DOL/IRS requirements; industry designations (e.g., QKA, CRPS) are a plus
• A commitment to service excellence and continuous improvement

This role will be based in either the New York City, Austin, King of Prussia, or Scottsdale office, and will be part of Vestwell's hybrid in-office operation.

The expected base salary range for this position is $80K - $95K base. This position is eligible to participate in the Company Bonus Pool and is eligible to receive new hire equity in the Company. Please note that salary bands are based on NY and other similar metro areas and may differ based on where the role is ultimately hired.