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.

Oswego County Opportunities, Inc. provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, creed, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, marital status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

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