Assistant Director - Transportation Services

Job Description

Job Description

Oswego County Opportunities, Inc. (OCO) is seeking a highly motivated and experienced Assistant Director of Transportation to support the leadership, administration, and strategic direction of our Transportation Division. This is an exciting opportunity for a transportation professional who is passionate about operational excellence, regulatory compliance, staff development, and community service.

Full-Time – Exempt
Standard schedule - 37.5 Hours Per Week / 52 Weeks Per Year (flexibility required)

Grade 19

Annual salary range: $61,776 - $88,000

JOB SUMMARY :

The Assistant Director of Transportation is a key leadership position that partners with the Director of Transportation to oversee the daily operations, strategic growth, and regulatory compliance of OCO's Transportation Division. Serving as the division's second-in-command, this role provides leadership in operations, staff development, fiscal management, program improvement, and service delivery to ensure safe, efficient, and customer-focused transportation services.

This position offers the opportunity to lead a dedicated team, drive continuous improvement initiatives, and make a meaningful impact on the individuals and communities we serve, while ensuring compliance with all Agency, State, and Federal regulations, policies, and procedures.

JOB DUTIES AND RESPONSIBILITIES :

Operational Oversight:

• Serves as second-in-command to the Director of Transportation; assumes leadership responsibility in the Director’s absence.
• Provides direct supervision to Transportation Supervisors, Managers, and administrative staff, and indirect oversight of all division personnel.
• Oversee daily operations of the Transportation Division, ensuring efficient service delivery, appropriate staffing, and system-wide coordination.
• Leads strategic planning, program development, and implementation of new transportation initiatives and service models.
• Ensures operational alignment with agency priorities, community needs, and contractual obligations.
• Participates in on-call rotation and provides administrative coverage for urgent and after-hours issues.

Quality Assurance & Compliance

• Ensures division-wide compliance with DOT, DMV (Article 19A), FTA, NYSDOT, and all regulatory requirements.
• Collaborates with internal stakeholders to conduct audits, monitor performance, and implement corrective action plans.
• Oversee incident reporting, investigations, and follow-up, ensuring adherence to regulatory and agency standards.
• Develops, implements, and maintains policies and procedures to ensure consistent, compliant operations.
• Ensures staff meet training, certification, and documentation standards, including drug and alcohol program compliance.

Fiscal Management & Performance Monitoring

• Plays a key role in budget development, forecasting, and financial oversight of the Transportation Division.
• Monitors expenditures, identifies cost efficiencies, and ensures fiscal responsibility across operations.
• Oversee billing processes including Medicaid, insurance, and fee-for-service programs, ensuring accuracy and compliance.
• Evaluates program performance using data, metrics, and reporting tools to drive operational improvements and outcomes.
• Supports and contributes to grant writing, reporting, and contract compliance activities.

Contracts, Vendors & External Relations

• Assists with managing vendor relationships and transportation service agreements
• Supports monitoring of contracts and funding requirements.
• Represents the Transportation Division in meetings, committees, and community partnerships as assigned.
• Assists with public information efforts to promote transportation services.

Fleet, Safety & Asset Management Support

• Provides leadership oversight of fleet operations, vehicle maintenance programs, and asset management systems.
• Ensures all vehicles meet safety, inspection, and regulatory requirements.
• Leads planning for vehicle procurement, replacement cycles, and capital improvements in collaboration with leadership.
• Promotes a culture of safety, risk management, and continuous improvement across transportation operations.

Staff Development & Supervision

• Provides coaching, supervision, and performance management to assigned staff.
• Participates in recruitment, hiring, onboarding, and retention strategies.
• Ensures employee development through training, mentorship, and engagement initiatives.
• Promotes a positive work culture, ensuring fair and consistent treatment of all employees.
• Builds leadership capacity within the division to support succession planning and operational continuity.

JOB REQUIREMENTS :

• Thorough knowledge of transportation operations, fleet management, and applicable regulatory frameworks (DOT, DMV, FTA, NYSDOT).
• Demonstrated experience in program oversight, compliance, fiscal management, and quality assurance.
• Strong leadership, organizational, and communication skills.
• Ability to analyze complex operational issues and implement effective solutions.
• Ability to work both independently and collaboratively in a fast-paced environment.
• Must maintain required certifications, including DMV Article 19A Examiner Certification.
• Must meet all Drug and Alcohol testing, background, and safety requirements.
• Valid driver’s license and ability to travel as required.

MINIMUM QUALIFICATIONS :

• Bachelor’s Degree in a related field and 1 – 3 years of closely related work and supervisory experience; or
• 5 years’ experience in a transportation system environment including supervisory and management experience and thorough knowledge of DOT regulations, inspections, and vehicles; or

• Any equivalent combination of education, experience, and training.
• Current valid Commercial Driver's License with Class B-P/S and Air Brake Endorsement preferred.

Apply today to join a mission-driven organization committed to strengthening our community through safe, reliable transportation services.