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Retirement Plan Implementation / Operations Manager, (HSR)

Chicago, IL

Who we are:

Strongpoint Partners is tech-enabled retirement services platform serving small- to mid-sized businesses with integrated retirement third party administration, recordkeeping, payroll, and HR solutions. Recognized as one of Inc. 5000’s Fastest Growing Private Companies in America and certified as a Great Place to Work, Strongpoint offers a suite of services that prioritizes accuracy, compliance, and reduction of regulatory risk for its clients, delivered by local client success teams that understand the nuances of the markets they serve. With a coast-to-coast network of 14 leading firms including HowardSimon, Jocelyn Pension Consulting, Retirement Strategies Group (“RSG”), Retirement Planners and Administrators (“RPA”), Pension Financial Services (“PFS”), Pollard & Associates, Carlson Quinn, SI GROUP, Retirement Planning Consulting Group (“RPCG”), Karel-Gordon & Associates, Cash Balance Actuaries, Pension Consultants, Inc. (“PCI”), Actuaries Unlimited (“AUI”), and CRP – California Retirement Plans (“CRP”), Strongpoint Partners combines a relentless passion for service and innovation with the experience and expertise required to make retirement work for everyone. For more information, please visit: www.strongpointpartners.com.  

About HowardSimon Retirement:

Based in Chicago, Illinois, HowardSimon Retirement is a large independent TPA with recordkeeping and advisory capabilities that offers integrated retirement, payroll, and HR solutions through a tech-enhanced service delivery model. HowardSimon is an operating partner of Strongpoint Partners, a leading tech-enabled financial services retirement platform backed by Shore Capital Partners (SCP).

Position Summary:

We are seeking a proactive and detail-oriented Retirement Plan Implementation & Operations Manager to join our growing third-party administration (TPA) firm. This role is ideal for someone with a strong background in retirement plan administration and operations, who also brings project management capabilities and the potential to grow into a broader leadership role.

The ideal candidate will have hands-on experience with retirement plan recordkeeping systems (Relius preferred), excellent organizational and communication skills, and a process-oriented mindset. You will be responsible for managing new plan onboarding, overseeing day-to-day operational workflows, supporting client service teams, and driving process improvements across our retirement plan practice.

PLEASE NOTE: This role is based in our Chicago, IL office and follows a hybrid work model, combining in-office collaboration with the flexibility to work remotely part of the week; however, consideration for a remote work arrangement will be considered for the right candidate.

Key Responsibilities:

  • Plan Implementation & Onboarding:
    • Lead the onboarding process for new retirement plans, including data collection, asset transfers, and plan set-up in Relius Administration.
    • Coordinate with internal and external stakeholders, (i.e., clients advisors, custodians, etc.), to ensure a smooth implementation.
    • Review plan documents and service agreements to align operations with plan provisions.
  • Plan Administration & Operations:
    • Maintain & oversee accurate plan data in the recordkeeping system, ensuring compliance with plan design and IRS/DOL requirements.
    • Manage account reconciliations, transaction processing, fee calculations, and contribution remittances.
    • Support annual compliance testing and government reporting processes in partnership with plan administrators.
  • Process & Project Management:
    • Identify areas for operational improvement and lead process enhancement initiatives.
    • Support internal projects related to automation, system improvements, and operational scalability.
    • Monitor key milestones and timelines across implementation and operational processes.
  • Team Collaboration & Leadership Support:
    • Work closely with the administrative and compliance teams to coordinate daily workflows and resolve issues.
    • Support training and mentoring of junior team members as needed.
    • Serve as a resource for operational questions, system troubleshooting, and client escalations.
  • Client Communication & Reporting:
    • Prepare and distribute custom plan and participant reports as needed.
    • Support communication around fund changes, plan updates, and fee disclosures.
    • Collaborate with relationship managers and client service teams to ensure a high-quality client experience.

Required Qualifications:

  • Bachelor’s degree in Business, Finance, or related field (or equivalent work experience).
  • 5+ years of experience in retirement plan administration, implementation, or operations—preferably in a TPA environment.
  • Strong knowledge of 401(k), 403(b), and other qualified plan types.
  • Demonstrated leadership skills and ability to manage and motivate a team.
  • Exceptional organizational, communication, and problem-solving abilities.
  • Experience managing account reconciliations, fee processing, and transaction workflows.
  • Proven ability to manage multiple projects, prioritize tasks, and meet deadlines.
  • Proficient in retirement plan recordkeeping platforms and CRM/project management tools.
  • Strong Excel skills, (VLOOKUPs, PivotTables, basic data analysis).

Preferred Qualifications:

  • Experience in a small or midsize TPA environment.
  • Exposure to plan conversions, mergers/acquisitions, or plan terminations.
  • Familiarity with other recordkeeping platforms or third-party systems.
  • Familiarity with data integration and file formats (e.g., payroll files, contribution files).

 

Our Value-Driven Employee Experience:

  • Flexible Workplace
  • Competitive PTO
  • Inclusive Environment
  • Development Opportunities
  • Comprehensive Benefits
  • Workplace Perks

 

 

 

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