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Director of People Operations

Chesapeake Search Partners

Job Description

CSP has partnered with a thriving, mission-driven nonprofit organization to identify a Director of People Operations. This is a unique opportunity for an experienced HR leader to shape and elevate the employee experience through innovative total rewards programs, strategic benefits administration, HR technology optimization, and strong compliance practices.

As a key member of the leadership team, this individual will lead the strategy, execution, and continuous improvement of the organization's People Operations function, with a primary focus on total rewards, benefits, HRIS management, workforce analytics, compliance, ADA accommodations, and leave administration. This role also serves as the organization's Affirmative Action/Equal Employment Opportunity, Ethics, and Title IX Compliance Officer.

What You'll Do

Lead People Operations Strategy

  • Develop and execute a people operations strategy that supports organizational growth, employee engagement, and operational excellence.
  • Build and enhance scalable HR systems, processes, and infrastructure that improve the employee experience.
  • Partner with executive leadership to align people programs with organizational goals and workforce planning initiatives.

Lead Total Rewards & Benefits Strategy

  • Oversee the design, administration, and continuous improvement of compensation, benefits, and total rewards programs.
  • Evaluate compensation structures and benefits offerings to ensure market competitiveness, internal equity, and employee satisfaction.
  • Manage relationships with benefits brokers, insurance carriers, retirement plan providers, and other key vendors.
  • Lead annual benefits renewals, open enrollment, and employee communications.
  • Develop strategies that attract, retain, and reward top talent while maintaining fiscal responsibility.

Own HRIS & Workforce Technology

  • Serve as the strategic owner of the HRIS, ensuring system optimization, reporting accuracy, data integrity, and user adoption.
  • Partner with IT and Finance on system integrations, enhancements, upgrades, and implementation projects.
  • Leverage technology to automate processes, improve reporting capabilities, and enhance operational efficiency.
  • Develop workforce dashboards and analytics that support informed business decisions.

Drive Compliance, ADA & Leave Administration

  • Ensure compliance with federal, state, and local employment laws and regulations.
  • Serve as the organization's subject matter expert for ADA accommodations, interactive process management, FMLA administration, disability programs, and leave management.
  • Develop and maintain HR policies, procedures, and compliance programs that mitigate risk and support organizational goals.
  • Partner with leadership and legal counsel on compliance initiatives, audits, regulatory matters, and policy governance.
  • Act as the organization's Affirmative Action, Equal Employment Opportunity, Ethics, and Title IX Compliance Officer.

Optimize People Operations

  • Oversee day-to-day HR operations including benefits administration, compensation programs, compliance, employee records management, onboarding, and policy administration.
  • Identify opportunities to streamline workflows, automate manual processes, and improve service delivery across the employee lifecycle.
  • Implement operational best practices that enhance efficiency and employee satisfaction.

Build & Develop High-Performing Teams

  • Lead, coach, and mentor members of the People & Culture team.
  • Foster a culture of accountability, collaboration, customer service, and continuous improvement.
  • Support strategic initiatives and organizational change efforts that advance the organization's mission.

What We're Looking For

Required Qualifications

  • 7+ years of progressive HR leadership experience with significant expertise in total rewards, benefits administration, HR operations, HRIS management, leave administration, and compliance.
  • Demonstrated experience leading compensation and benefits programs, including vendor management, plan administration, benchmarking, and program design.
  • Strong working knowledge of ADA, FMLA, leave management, workers' compensation, and employment law compliance.
  • Experience serving as the primary administrator or strategic owner of an HRIS platform.
  • Proven success improving HR systems, processes, reporting, and operational efficiency.
  • Strong understanding of federal, state, and local employment laws and regulations.
  • Exceptional communication, stakeholder management, and relationship-building skills.
  • Strong project management, analytical, and problem-solving capabilities.
  • Ability to balance strategic priorities with operational execution.
  • High level of integrity, discretion, and sound judgment.

Preferred Qualifications

  • Bachelor's degree in Human Resources, Business Administration, or a related field.
  • Master's degree and/or HR certifications such as SHRM-SCP, SPHR, CEBS, or CCP preferred.
  • Experience leading HRIS implementations, upgrades, or system transformations.
  • Experience within a nonprofit or other mission-driven organization is a plus.

Why This Opportunity?

  • Join a respected nonprofit organization making a meaningful impact in the community.
  • Serve as the organization's lead expert for Total Rewards, Benefits, HRIS, Compliance, and Leave Administration.
  • Influence organizational strategy as a key member of the leadership team.
  • Drive modernization and continuous improvement across People Operations and HR technology.
  • Lead a comprehensive total rewards function that directly impacts employee attraction, retention, and engagement.
  • Build scalable programs and processes that will create a lasting impact on the organization and its employees.

Ideal Candidate

The ideal candidate is a strategic People Operations leader with deep expertise in Total Rewards, Benefits Administration, HRIS management, ADA accommodations, leave administration, and compliance. This role is best suited for someone who thrives on building scalable processes, leveraging technology, analyzing workforce data, and creating programs that enhance both the employee experience and organizational effectiveness. Employee relations experience is beneficial, but the primary focus of this position is operational leadership, total rewards strategy, compliance, and HR systems optimization.

Vacancy posted 3 days ago
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