Director of Contract Operations

Didlake, Inc. is a non-profit rehabilitation services organization. At Didlake, creating opportunities that enrich the lives of people with disabilities is our mission. Since 1965, Didlake has served thousands of people with significant disabilities by providing training, job placement, employment opportunities, and day support services. We provide rewarding and purposeful work.

Why This Role Matters

The Director of Contract Operations serves as the senior operational leader for a diverse portfolio of custodial and grounds maintenance contracts across the Greater Hampton Roads Area (GHRA) and Southern Maryland. This role is critical to ensuring operational excellence, contract compliance, financial performance, customer satisfaction, and workforce development while supporting Didlake's mission of creating employment opportunities and career pathways for individuals with disabilities.

The Director drives strategic execution across multiple federal, municipal, and commercial contracts, ensuring alignment between field operations and corporate objectives while fostering a culture of accountability, safety, continuous improvement, and customer-focused service delivery.

What You Will Do

Lead Regional Operations

• Provide strategic leadership and operational oversight for all assigned custodial and grounds maintenance contracts.
• Ensure compliance with contract requirements, Statements of Work (SOW), Performance Work Statements (PWS), quality standards, and regulatory requirements.
• Serve as the primary operational liaison with customer agencies, contracting officers, inspectors, and client leadership.
• Lead contract mobilizations, start-ups, transitions, expansions, and service modifications.
• Drive operational consistency, process standardization, risk mitigation, and continuous improvement initiatives.
• Support strategic planning, regional growth initiatives, and long-term operational scalability.

Develop and Lead High-Performing Teams

• Provide coaching, guidance, and performance management for Operations Managers, Project Managers, Supervisors, and site leadership teams.
• Build leadership pipelines and succession plans to strengthen organizational capability.
• Foster a culture centered on safety, accountability, professionalism, employee engagement, and operational excellence.
• Partner with Human Resources, Recruiting, and Rehabilitation Services to support staffing, retention, training, and workforce integration initiatives.
• Champion Didlake's mission by supporting employment opportunities for individuals with disabilities.

Manage Financial Performance

• Develop and oversee operational budgets across assigned contracts and regional activities.
• Monitor labor utilization, overtime, subcontractor expenses, equipment costs, overhead, and profitability.
• Analyze financial performance metrics and implement corrective actions to improve efficiency and fiscal responsibility.
• Oversee procurement activities, vendor relationships, subcontractor performance, and resource allocation.
• Support forecasting, operational reporting, and executive performance reviews.

Oversee Custodial and Grounds Operations

• Ensure custodial operations meet sanitation, quality, infection prevention, and customer service standards.
• Direct landscape maintenance, turf management, irrigation, horticulture, tree care, and exterior facility operations.
• Develop and manage grounds maintenance work loading models, seasonal programs, staffing plans, and equipment utilization strategies.
• Oversee fleet readiness, preventive maintenance programs, and asset lifecycle management.
• Ensure compliance with OSHA, EPA, CDC, environmental, and safety regulations.

Drive Cross-Functional Collaboration and Emergency Preparedness

• Collaborate with Human Resources, Recruiting, Finance, Safety, Quality Assurance, Purchasing, and Rehabilitation Services to support operational success.
• Lead cross-functional reviews focused on quality, customer satisfaction, workforce stability, and operational execution.
• Maintain readiness plans for emergency response, severe weather, continuity of operations, and snow and ice removal activities.
• Coordinate emergency operational support with customer agencies and corporate leadership as needed.

What You Bring

• Proven ability to lead large-scale, multi-site operations in a government contracting environment.
• Strong experience managing custodial and/or grounds maintenance services.
• Demonstrated success building and developing high-performing operational teams.
• Ability to balance customer expectations, contract compliance, workforce development, and financial performance.
• Commitment to fostering inclusive workplaces and supporting employment opportunities for individuals with disabilities.
• Education & Experience
• Bachelor's degree in Business, Facilities Management, Horticulture, Landscape Management, or a related field required.
• Minimum of 7–10 years of progressive leadership experience managing federal contract operations.
• Demonstrated experience overseeing custodial and/or grounds maintenance services.
• Experience working with government contracts and regulatory compliance requirements required.
• Skills & Abilities
• Ability and willingness to travel throughout the Greater Hampton Roads Area and Southern Maryland.
• Ability to obtain and maintain site-specific security clearances.
• Strong leadership, communication, interpersonal, and negotiation skills.
• Excellent problem-solving and decision-making abilities.
• Strong financial acumen with experience managing budgets and operational performance metrics.
• Advanced knowledge of grounds maintenance production rates and workloading methodologies.
• Knowledge of FAR, OSHA, EPA, CDC, and related safety and regulatory requirements.
• Proficiency in Microsoft Office and operational reporting systems.
• Ability to analyze data, identify trends, and implement performance improvements.
• Ability to effectively train, coach, and resolve personnel issues through constructive conflict resolution.
• Ability to interact effectively and supportively with individuals with disabilities.
• Ability to maintain a professional image and build strong customer relationships.

Benefits

• Health coverage for you and your family through Medical, Dental, Vision plans
• Life Insurance/AD&D
• Disability Insurance
• Employee Assistance Program (EAP) for work and personal support
• 401(k) retirement plan with company match
• Paid time off and sick leave that begins accruing upon hire
• Employee Development Program (EDP)
• Paid holidays
• Direct deposit