Managing Director, Retirement – Pooled Plan Operations
Location: Remote
Compensation: Competitive base salary, up to 10% employer retirement match, equity participation, and home office support
Harrison Gray Search is representing a mission-driven retirement services organization seeking a dynamic and experienced leader to serve as Managing Director, Retirement. This is a rare opportunity to take on a foundational leadership role within a newly formed pooled employer plan (PEP) structure designed to modernize retirement access for employees in the public sector.
If you’re energized by building something new, shaping operational frameworks, and driving impact in the retirement space—this is the opportunity to do so with purpose and autonomy.
About the Organization
Our client is a newly launched, public-purpose startup that provides modern, fiduciary-first pooled retirement plans with the goal of delivering secure, portable retirement income to educators and school staff.
The organization's mission is to combine the financial stability of traditional pensions with the flexibility of modern retirement planning, helping employers offer better solutions and participants build lasting retirement security. It operates with the backing of a respected nonprofit and is structured to balance innovation, public service, and fiduciary excellence.
Why This Role Is Unique
- First-mover opportunity: Play a pivotal role in the launch and success of a nationwide pooled plan initiative
- Strategic and operational: Lead plan administration, vendor oversight, and participant experience
- Mission-aligned: Help build retirement security for the public-sector workforce
- Executive-level visibility: Work directly with the CEO and board fiduciary committee
- Start-up energy with stability: Operate within a well-capitalized, impact-focused environment
What You'll Do
- Oversee all aspects of pooled plan operations, including recordkeeping, administration, and regulatory compliance
- Build and manage relationships with key vendors (recordkeepers, TPAs, custodians)
- Coordinate employer onboarding and ensure an exceptional plan sponsor experience
- Lead annual audits, filings (Form 5500), and participant-level transaction oversight
- Own the RFP and selection process for external providers
- Collaborate with leadership to design governance structures and reporting practices
- Serve as the primary liaison to the Board’s Fiduciary Committee, ensuring full compliance and transparency
- Implement risk management practices and support participant servicing infrastructure
What We’re Looking For
- 7+ years in retirement plan operations, recordkeeping, or fiduciary governance
- Deep knowledge of ERISA, fiduciary responsibilities, and best practices for PEPs
- Experience managing vendor relationships and overseeing audits or regulatory filings
- Strategic thinker with strong execution, communication, and leadership skills
- Bachelor’s degree required; JD or ASPPA designation a plus
Bonus Points For
- Direct experience implementing or managing a Pooled Employer Plan under the SECURE Act
- Leading recordkeeper conversions and employer onboarding at scale
- Familiarity with cybersecurity controls (SOC 1/SOC 2 or NIST frameworks)
- Understanding of public-sector employer needs or charter school operations (not required, but valuable)
Compensation & Benefits
- Competitive salary
- Up to 10% employer match on retirement contributions
- Equity participation (RSAs, RSUs, or SARs)
- Health benefits with maximum HRA contribution
- Home office support provided
This is a rare opportunity to lead, shape, and grow a pioneering solution in the retirement plan space. If you're ready to make an impact, we’d love to hear from you.