Senior Specialist, Plan Design

Vestwell is the financial technology company powering the new savings economy. Our platform redefines how people save for the critical aspects of life across retirement, education, and healthcare savings needs.

Today, Vestwell enables over 350,000 businesses and over 2M active savers, with over $50B in assets saved across all 50 states.

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? Vestwell is expanding and we’re excited about adding a Senior Specialist to our Retirement Services team who is passionate about our mission to change the retirement FinTech space. At a high level, we’re looking for a dedicated consultant to support our Sales, Onboarding, Plan Design and Plan Documents teams in document creation and consultation with new and existing sponsors on their desired plan features. Ideally, you have spent several years working with sponsors, recordkeepers and/or TPAs and have dedicated some time servicing the plan design, compliance and plan document sides of qualified/non-qualified plan servicing.

What Will You Be Doing? As a Senior Specialist, you will be responsible for independently interpreting ERISA and other applicable retirement plan laws to consult, amend, and maintain compliant retirement plan documents. This role requires advanced legal and regulatory knowledge, sound judgment, and the ability to translate Plan Sponsors’ business goals into plan documents that align with Vestwell platform capabilities and operational requirements. You will act as a key subject matter expert, partnering closely with internal teams and Plan Sponsors to ensure accuracy, compliance, and scalability of plan documentation.

Your Responsibilities Will Include, But Are Not Limited To

• Plan Design Consultation: Collaborate with Plan Sponsors to create optimal defined contribution plan designs, addressing queries, and ensuring a clear understanding of chosen plan specifications for both new sponsors setting up their plan and existing sponsors with plan amendments.
• Plan Document Review: Support sales in conversion contract considerations by performing a plan spec review against supported and outsourced design models; capture plan design conversations and decisions from presale, sale, and onboarding processes to create new plan documents.
• Regulatory Interpretation & Compliance Expertise: Independently interpret ERISA and other applicable laws, regulations, and guidance to create, amend, and restate retirement plan documents that are legally compliant and operationally sound.
• Plan Document Drafting & Maintenance: Prepare plan documents, including discretionary and interim amendments, restatements, participant notices, and related disclosures, ensuring consistency with plan design decisions and platform capabilities
• Independent Judgment & Analysis: Exercise discretion in evaluating plan design requests, assessing legal and operational risk, and determining appropriate document structures with minimal supervision.
• Cross-Functional Collaboration: Work closely with Onboarding, Retirement Plan Administration, Client Success, and Employer Services teams to ensure plan documents support seamless implementation and ongoing administration.
• Process & Documentation Improvement: Support and contribute to process reviews, research, and documentation related to plan document operations, corrections, and audit support.
• Project Management: Design and manage workflows for novel and recurring large-scale document projects, ensuring timely, accurate, and scalable execution.
• Product & Automation Support: Partner with Product teams to improve document automation, technology-supported drafting processes, and overall plan document management capabilities.

Requirements The Necessities

• Subject Matter Expertise - Understanding of Employee Retirement Income Security Act (ERISA), Department of Labor (DOL), Internal Revenue Service (IRS) regulations
• At least 5 years of experience in qualified/non-qualified plans including sales support, design consultation, document drafting, and non-discrimination testing
• Keen attention to detail, deadlines, and customer service needs along with strong communication skills
• Collaborative approach with internal stakeholders and with cli…