Training Manager, Employer Services

Vestwell • Austin, NY

9d • Hybrid

About The Position

Vestwell is seeking a Training Manager to own the full training ecosystem for Employer Service specialists supporting 401(k) plan sponsors, HR and payroll administrators, and partners such as third-party administrators and financial advisers. The role works closely with Employer Service leadership, Plan Onboarding, Operations, Compliance, and product teams to prepare employees to deliver an excellent employer experience.

The Training Manager leads new-hire onboarding from day one through proficiency, including instructor-led, virtual, and hands-on training, nesting and shadowing plans, and readiness assessments. The role develops and maintains learning materials covering 401(k) fundamentals and employer-facing workflows, while keeping content current with company policy and applicable regulatory requirements.

The position also provides ongoing development and specialized learning paths, coordinates a training calendar, evaluates training outcomes, and reports on training impact. It partners with leaders to address skill gaps, prepares teams for product and system releases, ensures required compliance and data-security training is delivered and documented, and upholds confidentiality and data-protection standards. The role is based in one of Vestwell’s New York City, Austin, King of Prussia, or Scottsdale offices and follows a hybrid in-office model. The expected base salary range is $80,000–$95,000, with eligibility for the Company Bonus Pool and new-hire equity.

Requirements

• 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.
• Ability to manage multiple priorities in a fast-paced environment.
• Working familiarity with ERISA and DOL/IRS requirements.
• Commitment to service excellence and continuous improvement.

Nice To Haves

• Familiarity with instructional design and learning management system (LMS) tools.
• Industry designations such as QKA or CRPS.

Responsibilities

• Own Employer Service specialist onboarding from the first day through full proficiency.
• Deliver engaging instructor-led, virtual, and hands-on training sessions.
• Design nesting and shadowing plans to transition new hires from classroom training to live work.
• Assess new-hire readiness through knowledge checks and practical exercises.
• Develop training on 401(k) plan fundamentals, including eligibility, vesting, contributions and match, loans, distributions, and payroll integration.
• Create training on employer-facing workflows, including 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 training 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.
• Build advanced and specialized learning paths to support career growth and cross-training.
• Manage a training calendar that balances team development with service-level needs.
• Track training completion, assessment results, time to proficiency, and post-training performance.
• Gather learner and leader feedback to improve training content and delivery.
• Report training impact to leadership and recommend improvements.
• Use performance and quality trends shared by supervisors to identify targeted training needs.
• Collaborate with supervisors and managers to understand skill gaps and team needs.
• Partner with product and engineering teams to prepare employees for new feature and system releases.
• Work with Compliance to deliver and document required regulatory and data-security training.
• Uphold confidentiality and data-protection standards in training materials and examples.

Benefits

• Comprehensive health benefits.
• Generous time off.
• Employee Wellbeing Committee.
• Hybrid work model with access to collaborative offices.
• Competitive 401(k) plan.
• Eligibility to participate in the Company Bonus Pool.
• Eligibility to receive new-hire equity in the Company.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed