Director of Operations

About the Role

The Director of Operations at CHR  is responsible for the daily functions and operational efficiency of the technical aspects of company, with oversight of operational teams across Implementation and IT. This role ensures compliance with applicable laws, optimizes departmental workflows, and executes executive management driven initiatives. The Director also provides leadership over CHR’s core technology platforms and data environment, combining operational leadership with strong systems, integration, and analytics expertise to strengthen service delivery, elevate client success, and position the organization for continued growth.

Key Responsibilities

Operations Management

• Build strong partnerships with HR, Tax, Accounting, Benefits, and Technology teams to facilitate efficient workflows.
• Assist Payroll and Tax teams with escalated complex PrismHR system operations requests.
• Evaluate and onboard new vendors and technology partners that meet the company’s needs and standards.
• Negotiate contracts and pricing with vendors to secure beneficial terms and cultivate relationships with operational vendors to secure favorable plan terms and performance.
• Lead and oversee the daily operations of the Implementation and IT departments
• Develop and implement strategies to optimize processes and mitigate risk, with particular focus on claim management, service quality, and regulatory compliance.
• Assess and prepare proposals for departmental operational optimization, ensuring smooth workflows and maintaining standards of excellence.
• Provide expertise on operational standards and best practices and maintain internal controls and recordkeeping standards.
• Review, advise on, and execute operational initiatives developed with CHR executive Leadership.

Process Optimization and Systems Transformation

• Lead efforts to automate, modernize, and optimize departmental workflows by fully leveraging PrismHR, ClientSpace, and outside vendor capabilities to translate manual or legacy processes into scalable, well-documented procedures.
• Lead change management and user adoption efforts, including requirements gathering, testing, go-live readiness, and post-implementation support, to ensure new systems and processes deliver intended value.
• Monitor and analyze departmental work to develop more efficient procedures and use of resources while maintaining a high level of accuracy.
• Design and implement special projects that further enhance the white glove approach to CHR’s services.

Technology, Systems, and Data Oversight

• Provide strategic oversight of CHR’s core platforms, including but not limited to PrismHR and ClientSpace, Epic, and internal Microsoft systems, ensuring configuration integrity, data accuracy, and alignment across departments and client environments.
• Oversee system integrations between internal platforms and third-party systems across their full lifecycle, from requirements and vendor coordination through testing, deployment, and post-launch support, ensuring seamless data flow and operational continuity.
• Ensure cybersecurity best practices and data governance standards are maintained across all CHR systems and client-facing platforms, including secure access management, user permissions, and system audit trails.
• Leverage knowledge of API integrations to develop seamless flows of information between internal systems and external third-party systems.

Client Success

• Serve as a senior escalation point for complex client and system concerns, driving timely resolution with urgency and professionalism.
• Consistently work with clients to transition operations toward a more self-reliant process, and support client growth, new services, and platform enhancements.
• Support proactive communication of regulatory updates, tax changes, and service enhancements relevant to clients, in coordination with HR and client success teams.
• Identify opportunities to upsell current clients on CHR service offerings not currently being utilized 

Qualifications

Required

• Demonstrated experience leading enterprise system implementations, software transitions, or large-scale process improvement initiatives end to end.
• Proven knowledge and proficiency in the ASO and PEO business models or ability to learn.
• Strong knowledge of federal, state, and local payroll and tax compliance requirements, including multi-state environments.
• Working knowledge of system integration methodologies, APIs, and third-party vendor management.
• Strong understanding of cybersecurity fundamentals and data governance best practices.
• Strong financial and analytical acumen, including experience overseeing operational reporting and data analysis.
• Excellent communication skills, with the ability to translate technical concepts for non-technical stakeholders and present confidently to executives and clients.
• Bachelor’s degree in Business, Accounting, Finance, Operations, Information Systems, or a related field, or equivalent experience.

Preferred

• Working knowledge of PrismHR and ClientSpace software highly preferred.
• Project management certification (e.g., PMP) or equivalent experience with structured delivery methodologies preferred.
• Background in data science, business intelligence, or HR analytics.
• MBA or other advanced degree in a related field preferred.

 Core Competencies

• Operational Leadership: Drives efficiency and accountability across multiple functions while maintaining quality.
• Systems Thinking: Approaches the organization with an infrastructure-first, integration-minded perspective.
• Accuracy and Compliance Orientation: Executes with precision and treats compliance as non-negotiable.
• Client Service Excellence: Communicates proactively and resolves issues with urgency and professionalism.
• Analytical Thinking: Identifies discrepancies, investigates root causes systematically, and uses data to inform decisions.
• Confidentiality and Data Governance: Maintains strict data security and integrity standards across all systems and records.
• Adaptability and Collaboration: Navigates changing regulations and client needs, and partners effectively across teams and vendors.