Director, Benefits Operations

Benefits are one of the most visible and impactful services we deliver to our clients and their employees. When benefits administration works seamlessly, employees receive the coverage they expect, employers trust our systems, and our clients can focus on running their businesses instead of solving administrative problems.

The Director of Benefits Operations ensures the stability, accuracy, and scalability of our benefits platform—from retirement plans to medical, dental, vision, and ancillary coverage. This leader builds the operational systems, processes, and teams that allow Employer Flexible to deliver on its promise to stabilize our foundation, elevate how we show up, and win by being the easiest partner to work with and the hardest to replace.

By leading both 401K administration and benefits operations, this role ensures that thousands of employees are properly enrolled, plans remain compliant, carrier integrations function correctly, and clients experience a benefits program that is reliable, responsive, and built to support their growth.

The Director of Benefits Operations leads the strategy, execution, and performance of the company’s benefits administration functions. This role oversees two core teams responsible for retirement plan administration and the operational management of employee benefit programs.

The Director ensures benefits plans are accurately configured in the company’s HRIS platform, employees are enrolled correctly, carrier integrations function reliably, and retirement plans operate in full compliance with regulatory requirements.

This leader is responsible for building scalable operational processes, developing high-performing teams, and ensuring benefits administration delivers an exceptional experience for both clients and their employees.

• Lead the strategy and execution of all Benefits Operations functions.
• Build scalable processes that support the growth of the PEO platform.
• Ensure operational accuracy, compliance, and efficiency across all benefits administration activities.
• Partner cross-functionally with Payroll, Client Success, Sales, Implementation, and Finance to ensure seamless service delivery.

• Oversee administration of the company’s Multiple Employer Plan (MEP).
• Ensure compliance with ERISA, DOL, and IRS requirements.
• Manage retirement plan operations including participation monitoring, plan setup, audits, contribution processing, and employee education.
• Lead the Manager, 401K Administration & Compliance and supporting specialists.

• Oversee setup and maintenance of client benefit plans within the HRIS platform.
• Manage EDI connectivity and carrier integrations for medical, dental, vision, and ancillary plans.
• Ensure employees are enrolled in the correct plans and eligibility data remains accurate across systems.
• Oversee carrier eligibility maintenance for client-level plans.
• Manage the full employee benefits lifecycle including new hire enrollments, qualifying life events, plan changes, and terminations.

• Develop operational expertise across key systems including:
  • Microsoft Office Suite
  • CRM Dynamics
  • Darwin/Cohesion HRIS platform (myHR 1.0 and myHR 2.0)
• Identify system improvements and automation opportunities that improve operational efficiency and reduce manual work.

• Lead and develop Benefits Operations managers and specialists.
• Conduct daily stand-ups, bi-weekly 1:1 meetings with direct reports, and bi-weekly Level 10/EOS team meetings.
• Establish clear expectations and accountability for team performance.
• Ensure leaders and teams embody the company’s core values:
  • Have Fun
  • Be Selective
  • Be Humble
  • No Surprises
  • Want It

• Participate in annual planning and budgeting.
• Manage departmental operating expenses within approved budgets.
• Monitor operational capacity and staffing ratios as the company grows.

Education

Bachelor’s degree in Business, Human Resources, Finance, or related field preferred.

Experience

• 8+ years of experience in benefits administration or retirement plan operations
• 3+ years of leadership experience managing operational teams
• Experience with benefits compliance, carrier integrations, and HRIS platforms

Preferred

• Experience working within a PEO or multi-employer environment
• Experience managing Multiple Employer Plans (MEP)
• Strong knowledge of benefits administration systems and operational processes