Director, Benefits Operations

Employer Flexible

$100K — $130K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Business, Human Resources, Finance, or related field preferred.
  • 8+ years in benefits administration or retirement plan operations.
  • 3+ years in leadership roles managing operational teams.
  • Experience with benefits compliance, carrier integrations, and HRIS platforms.
  • Preferred: Experience in a PEO or multi-employer environment.

Responsibilities

  • Lead overall strategy and execution of Benefits Operations functions.
  • Build scalable processes for the PEO platform's growth.
  • Ensure compliance and operational accuracy in all benefits administration activities.
  • Collaborate with Payroll, Client Success, Sales, and Finance for seamless service delivery.
  • Oversee administration of the Multiple Employer Plan (MEP) and ensure regulatory compliance.
  • Manage employee benefits lifecycle from enrollment to terminations.
  • Identify system improvements for operational efficiency and automation.

Benefits

  • Dynamic work environment focusing on team development and leadership.
  • Opportunities for professional growth within a rapidly expanding organization.
  • Focus on creating a fun and collaborative workplace aligned with core values.
Full Job Description
Position Summary

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.
Key Responsibilities
Operational Leadership
  • 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.
401K Administration & Compliance
  • 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.
Benefits Operations
  • 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.
Systems & Technology
  • 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.
Leadership & Team Development
  • 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
Financial & Operational Accountability
  • Participate in annual planning and budgeting.
  • Manage departmental operating expenses within approved budgets.
  • Monitor operational capacity and staffing ratios as the company grows.
Qualifications

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

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