Demo

Director of Benefits

Chesapeake Search Partners
Baltimore, MD Full Time
POSTED ON 11/11/2026
AVAILABLE BEFORE 12/9/2026

CSP has partnered with a thriving, mission-driven nonprofit organization to identify an impactful Director of People Operations/Benefits/Total Rewards. This is a unique opportunity for an experienced HR leader to shape the employee experience, build scalable people strategies, and drive operational excellence across a growing organization dedicated to making a difference in the communities it serves.

As a key member of the leadership team, the Director of People Operations will lead the strategy, execution, and continuous improvement of all People & Culture operations, including HR compliance, compensation, total rewards, HRIS, employee relations, workforce analytics, and organizational policies. 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 forward-thinking People Operations strategy that supports organizational growth, culture, and long-term business objectives.
  • Build and enhance scalable HR systems, processes, and infrastructure that create an exceptional employee experience.
  • Partner with executive leadership to drive organizational effectiveness and workforce planning initiatives.

Elevate HR Operations

  • Oversee all aspects of People & Culture operations, including compensation, benefits, HRIS administration, compliance, employee records, and policy development.
  • Identify opportunities to streamline processes, increase efficiencies, and improve service delivery across the employee lifecycle.
  • Implement best practices and technology solutions that enhance operational performance and employee engagement.

Drive Data & Technology Initiatives

  • Serve as the strategic owner of the HRIS, ensuring system optimization, data integrity, reporting, and functionality.
  • Collaborate with IT and Finance to implement system enhancements, integrations, and upgrades.
  • Develop meaningful workforce metrics, dashboards, and executive reporting that drive informed decision-making across the organization.

Champion Compliance & Employee Relations

  • Ensure compliance with federal, state, and local employment laws and regulations.
  • Partner closely with leadership and legal counsel on compliance initiatives, risk management, investigations, and policy governance.
  • Serve as a trusted resource for complex employee relations matters and provide guidance on workplace issues and resolutions.
  • Act as the designated People & Culture leader in the absence of senior HR leadership.

Lead Total Rewards & Leave Administration

  • Oversee compensation programs and a highly competitive total rewards strategy designed to attract and retain top talent.
  • Manage benefits vendor relationships and evaluate programs to ensure market competitiveness and cost effectiveness.
  • Lead ADA accommodations, FMLA administration, and other leave management processes while ensuring compliance and a positive employee experience.

Build & Develop High-Performing Teams

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


What We're Looking For

Required Qualifications

  • 5 years of progressive HR leadership experience with a strong background in HR operations, compliance, employee relations, compensation, and benefits.
  • Demonstrated success leading HR initiatives in a complex and growing organization.
  • Strong knowledge of federal, state, and local employment laws and regulations.
  • Experience managing HRIS platforms and leveraging data and analytics to influence business decisions.
  • Exceptional communication and relationship-building skills with the ability to influence stakeholders at all levels.
  • Strong project management, problem-solving, and organizational skills.
  • Ability to balance strategic priorities with day-to-day 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 certification (SHRM-CP, SHRM-SCP, PHR, SPHR) preferred.
  • Experience within a nonprofit or mission-driven organization is a plus.


Why This Opportunity?

  • Join a respected nonprofit organization making a meaningful impact in the community.
  • Influence organizational strategy as a key member of the leadership team.
  • Lead transformational HR initiatives that elevate culture, engagement, and performance.
  • Oversee a comprehensive total rewards program and modern people operations function.
  • Enjoy the opportunity to build, innovate, and leave a lasting impact within a growing organization.


Salary : $130,000 - $140,000

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