Remote Wind Point Partners Jobs in Chicago, IL (NOW HIRING)

Position Summary: 

Strongpoint Partners is seeking an experienced and entrepreneurial Director, TPA Operations, Strategic Partnerships to lead the administration, growth, and strategic development of a defined contribution retirement plan practice within the Strongpoint platform.

This senior leadership role is responsible for overseeing retirement plan operations, managing key client and advisor relationships, supporting partner firms across the Strongpoint network, and building the team, processes, and infrastructure necessary to support long-term growth. The ideal candidate is a seasoned TPA professional with extensive experience managing complex retirement plan portfolios, leading administration teams, and serving as a trusted consultant to plan sponsors, advisors, and industry partners.

The Director will operate as both a strategic leader and hands-on technical resource, driving operational excellence while contributing to business development initiatives, acquisitions and integrations, talent development, and financial performance. This individual must be comfortable moving between executive-level strategy discussions and detailed plan administration work as business needs require.

PLEASE NOTE: Our preference is for this role to be based at our Chicago headquarters, either in-person or following a hybrid work model. However, we are open to considering fully remote arrangements for highly qualified candidates.

Key Responsibilities:

• Plan Administration & Compliance Leadership
  • Provide oversight for a diverse portfolio of defined contribution retirement plans, including owner-only plans, safe harbor plans, cross-tested plans, ESOPs, and large audited plans.
  • Ensure timely and accurate completion of annual compliance testing, Form 5500 filings, participant disclosures, and all required regulatory reporting.
  • Serve as a technical resource and escalation point for complex compliance, operational, and plan design matters.
  • Support Plan Administrators through annual audits, IRS and Department of Labor examinations, plan corrections, voluntary compliance programs, and plan terminations.
  • Consult on merger and acquisition activity impacting retirement plans, providing guidance on plan mergers, asset transfers, and operational integration requirements.
  • Monitor legislative and regulatory developments and communicate implications to clients, advisors, and internal teams.
  • Establish and maintain operational procedures, quality control standards, and best practices that promote consistency and scalability.
• Strategic Partnership Support & Capacity Management
  • Serve as a resource for Strongpoint's affiliated TPA partner firms during periods of capacity constraints, staffing transitions, or other operational needs.
  • Coordinate temporary or transitional administration services for partner firm clients while maintaining service continuity and client satisfaction.
  • Collaborate closely with partner firm leadership to facilitate seamless transitions of plan administration responsibilities.
  • Act as a technical consultant and operational resource for partner firms facing complex plan issues, regulatory challenges, or administrative questions.
  • Foster strong relationships across the Strongpoint partner network while respecting and preserving existing client and advisor relationships.
  • Maintain transparency with Strongpoint leadership regarding resource allocation, portfolio management, and partner support activities.
• New Business Onboarding & Book Conversion Management
  • Lead the onboarding, conversion, and implementation of new retirement plan clients and transferred books of business entering the Strongpoint network.
  • Oversee onboarding and document teams responsible for plan setup, document preparation, recordkeeper coordination, payroll integration, and participant communications.
  • Design, document, and continuously improve onboarding workflows, conversion processes, and quality assurance procedures.
  • Develop scalable operational frameworks to support future growth and acquisition activity.
  • Partner with Strongpoint's M&A and integration teams to facilitate retirement plan transitions associated with newly acquired firms.
  • Monitor onboarding timelines and client experience metrics to ensure successful implementations.
• Client & Advisor Relationship Management
  • Serve as the senior relationship manager for assigned plan sponsor clients and key advisor relationships.
  • Lead plan design consultations, annual review meetings, fiduciary discussions, and ongoing strategic planning conversations.
  • Provide clients with cost-benefit analyses and recommendations regarding plan design enhancements, compliance strategies, and participant outcomes.
  • Manage escalated service issues and complex operational challenges while maintaining client confidence and trust.
  • Participate in advisor presentations, prospect meetings, industry events, and business development opportunities.
  • Build and maintain long-term relationships with financial advisors, consultants, recordkeepers, and other strategic partners.
• Team Leadership & Talent Development
  • Recruit, hire, onboard, and develop retirement plan administration professionals as the business grows.
  • Create a high-performance culture focused on client service, accountability, collaboration, and continuous improvement.
  • Assign and balance workloads based on plan complexity, staff capabilities, and organizational priorities.
  • Conduct performance evaluations, establish development plans, and administer compensation and incentive programs.
  • Provide technical training, coaching, and mentorship to strengthen team capabilities and succession planning.
  • Identify opportunities to improve employee engagement, retention, and career progression within the organization.
• Financial Management & Strategic Leadership
  • Own and manage the business unit profit and loss statement, understanding the financial impact of staffing, pricing, technology, and operational decisions.
  • Develop and monitor budgets, forecasts, staffing plans, and productivity metrics.
  • Identify opportunities to improve profitability, operational efficiency, and service delivery.
  • Collaborate with executive leadership on strategic planning, growth initiatives, acquisition integration, and long-term business objectives.
  • Evaluate technology solutions, vendor relationships, and operational investments that support scalability and client experience.
  • Establish and track key performance indicators related to service delivery, employee performance, client satisfaction, and financial results.

Minimum Qualifications:

• Bachelor's degree in Business, Finance, Accounting, Economics, Human Resources, or a related field.
• 10+ years of retirement plan administration experience within a Third-Party Administrator (TPA), consulting firm, recordkeeper, or related retirement services organization.
• Demonstrated experience managing complex defined contribution retirement plans and plan sponsor relationships.
• Strong technical knowledge of ERISA, Internal Revenue Code qualification requirements, IRS and DOL regulations, compliance testing, Form 5500 reporting, and plan correction programs.
• Previous experience leading teams, managing performance, and developing retirement plan professionals.
• Proven ability to manage multiple priorities while maintaining exceptional service standards.
• Excellent communication, presentation, consulting, and relationship management skills.
• Strong analytical, organizational, and problem-solving capabilities.

Preferred Qualifications:

• ASPPA credentials such as QKA, QKC, CPC, QPA, TGPC, or equivalent industry certifications.
• Experience supporting retirement plan transitions related to mergers and acquisitions.
• Prior responsibility for departmental budgeting, financial management, or P&L oversight.
• Experience implementing operational improvements and scaling service organizations.
• Familiarity with multiple recordkeeping platforms and retirement plan administration systems.

What Success Looks Like:

• Consistently delivers exceptional service and compliance outcomes across a diverse retirement plan portfolio.
• Successfully supports Strongpoint partner firms through operational challenges while maintaining strong relationships.
• Builds scalable onboarding and administration processes that support business growth.
• Develops a high-performing team with strong technical expertise and client service capabilities.
• Contributes meaningfully to revenue growth, profitability, and strategic initiatives.
• Serves as a trusted advisor to clients, financial advisors, partner firms, and executive leadership.

Pay Transparency Statement:

The anticipated pay range for this position is $150,000-$175,000 annually plus potential annual bonus.

At Strongpoint Partners, our salary ranges reflect the minimum and maximum base pay for the posted position applicable to all locations across the US. Within the posted salary range, individual pay is determined by the geographic location, job related skills, experience, education, and certifications. Our total compensation package includes base pay plus a comprehensive benefits program.