Total Rewards Director

Endeavor Schools, LLC

$100K — $130K *
US-AnywhereRemote in United States
Education, Government & Non-Profit
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Human Resources, Business Administration, or related field (or equivalent experience).
  • 8+ years of experience in Total Rewards, Benefits Administration, or related HR roles.
  • Experience managing benefits for a multi-state workforce.
  • Strong knowledge of employee benefits and retirement regulations (FMLA, ADA, etc.).
  • Demonstrated experience managing vendors, brokers, and third-party administrators.
  • Excellent analytical, communication, and relationship-building skills.
  • Ability to manage multiple priorities with attention to detail.

Responsibilities

  • Lead strategy and administration of employee benefit programs including wellness initiatives and Open Enrollment.
  • Oversee 401(k) retirement plan management, vendor coordination, compliance, and employee education.
  • Partner with Regional HR Directors to manage leave administration (FMLA, state-specific leaves).
  • Serve as primary relationship manager for benefits brokers and retirement providers.
  • Collaborate with Finance on budgeting and strategic planning for Total Rewards.
  • Create employee communications and educational resources for benefits.
  • Act as escalation point for complex benefits questions and provide support.
  • Monitor regulations for ongoing compliance and effectiveness of programs.

Benefits

  • Collaborative HR leadership environment.
  • Opportunity to make a meaningful impact on employee experience and organizational growth.
Full Job Description
Job Details

We9re looking for an experienced Director of Total Rewards to lead our benefits, retirement, and leave programs while helping us deliver an outstanding employee experience across our growing organization.

The Director of Total Rewards is responsible for developing and leading Endeavor Schools9 Total Rewards strategy, ensuring our benefits, retirement, and leave programs remain competitive, compliant, and aligned with our business goals.

This highly collaborative role partners with HR Leadership, Finance, vendors, and operational leaders to support a diverse, multi-state workforce. You9ll have the opportunity to shape programs that help us attract, retain, and care for our employees while continuously improving the employee experience.

As our Director of Total Rewards, you will:

  • Lead the strategy, design, and administration of all employee benefit programs, including medical, dental, vision, life, disability, voluntary benefits, wellness initiatives, and annual Open Enrollment.

  • Oversee the administration and governance of the company9s 401(k) retirement plans, including vendor management, compliance, and employee education.

  • Partner with Regional HR Directors to oversee leave administration, including FMLA, ADA accommodations, state and local leave programs, and company-sponsored leaves.

  • Serve as the primary relationship manager for benefits brokers, retirement providers, and third-party administrators.

  • Partner with Finance and HR Leadership on budgeting, forecasting, cost analysis, and strategic planning related to Total Rewards.

  • Develop employee communications and educational resources that make benefits easy to understand and accessible.

  • Serve as the escalation point for complex benefits and leave questions, providing timely, accurate, and compassionate support.

  • Monitor changing federal, state, and local regulations to ensure ongoing compliance.

  • Develop reporting and analytics to evaluate program effectiveness, utilization, and employee engagement.

  • Collaborate closely with Talent Acquisition, HR Operations, HR Business Partners, Payroll, and Finance to deliver a seamless employee experience.

  • Drive continuous improvement by identifying opportunities to simplify processes, enhance service delivery, and improve employee satisfaction.

Required Qualifications
  • Bachelor9s degree in Human Resources, Business Administration, or a related field (or equivalent combination of education and experience).

  • Eight or more years of progressive experience in Total Rewards, Benefits Administration, or related Human Resources roles.

  • Experience managing employee benefits for a multi-state workforce.

  • Strong knowledge of federal and state regulations related to employee benefits, retirement plans, FMLA, ADA, and leave administration.

  • Demonstrated experience managing vendors, brokers, and third-party administrators.

  • Excellent analytical, communication, and relationship-building skills.

  • Ability to manage multiple priorities while maintaining exceptional attention to detail.

Preferred Qualifications
  • Experience supporting Education, Healthcare, or other highly regulated industries.

  • Experience working within a high-growth, multi-site organization.

  • Professional certifications such as CEBS, SHRM-CP, SHRM-SCP, or CCP.

At Endeavor Schools, you9ll join a collaborative HR leadership team focused on supporting employees who make a difference every day. We offer the opportunity to make a meaningful impact by designing programs that enhance the employee experience while helping our organization continue to grow.

If you9re passionate about building exceptional Total Rewards programs and enjoy partnering across the business to create solutions, we9d love to hear from you.

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