Director of Transportation

Restoring Our Youth Organization Inc.; Chicago (IL); Hybrid; USD 95,000 - 130,000; Full time

Benefits offered by this job

Remote work opportunities

Flexible schedule

Mentorship from leadership

Volunteer hours & résumé-building

Travel/meals reimbursement

Professional development

Job summary

Restoring Our Youth Organization Inc. in the Chicagoland area seeks a Director of Transportation to lead logistics, fleet management, and transit operations for programs serving youth and communities.

You will supervise transportation staff, develop budgets, optimize routes, ensure DOT compliance, and collaborate with senior leadership to expand safe, cost-efficient services while supporting ROYO’s mission.

Qualifications

• Bachelor's degree in logistics, transportation, business, or a related field is required.
• Minimum 2–5 years of experience in transportation management/logistics.
• Nonprofit/public service experience is preferred.
• Strong leadership, communication, and budgeting skills.
• CDL preferred or ability to obtain one.

Responsibilities

• Oversee daily transportation services including route planning, dispatching, and vehicle maintenance.
• Enforce safety regulations; manage accidents; ensure DOT/state compliance as needed.
• Recruit, train, and supervise transportation staff (drivers, supervisors, dispatchers).
• Develop and manage the transportation budget (fuel, maintenance, purchasing).
• Identify opportunities to improve efficiency, reduce costs, and adopt new technology.
• Develop long-range plans and policies for the department.

Skills

Leadership

Organizational skills

Time management

Communication

DOT compliance

Budgeting

Staffing

CDL preferred

Education

Bachelor's in logistics or related field

Tools

Google Suite

Job description

About Restoring Our Youth Organization Inc. (R.O.Y.O.)

At Restoring Our Youth Organization Inc. (R.O.Y.O), we believe that every person no matter their circumstances has the potential to thrive when given the right opportunities, guidance, and support. Our goal is to empower vulnerable youth and communities to overcome challenges and begin their journey toward restoration and success. At Restoring Our Youth Organization Inc. , we believe in equal opportunity and inclusive growth. Our volunteers are expected to dedicate a minimum of 8 to 10 hours a week. Every role here matters and every team member helps us move closer to a world where every community feels seen, supported, and capable of success.

About the Role

Reporting to the Executive Vice President of Operations, the Director of Transportation plays a critical leadership role in overseeing the organization’s logistics, fleet management, and transit operations. This position ensures the safe, efficient, and compliant movement of goods and program participants across all service areas. Key responsibilities include supervising transportation personnel, developing and managing departmental budgets, optimizing routing and scheduling, and ensuring full adherence to federal and state transportation regulations.

What You’ll do

• Operations Management: Oversee daily transportation services, including route planning, dispatching, and vehicle maintenance.
• Safety and Compliance: Enforce safety regulations, manage accident investigations, and ensure compliance with Department of Transportation (DOT) and state regulations when needed.
• Leadership and Staffing: Recruit, train, and supervise transportation staff, including drivers, supervisors, and dispatchers.
• Budgeting and Cost Control: Develop and manage the transportation budget, including fuel costs, maintenance, and purchasing.
• Logistics and Efficiency: Identify opportunities for improving efficiency, reducing costs, and implementing new technology.
• Strategic Planning: Develop long-range plans, policies, and procedures for the department

What You Bring

• Must be located in the United States of America, preferably in the Chicagoland area.
• Solid leadership skills organizational and time-management skills
• Highly organized and collaborative
• Outstanding communication, interpersonal and leadership skills, with attention to detail
• Minimum of 2-5 of experience in transportation management, logistics, fleet operations, or a closely related field, preferably within nonprofit, public service, or volunteer‑driven environments.
• Proficiency in route planning in the Chicagoland area, scheduling, and fleet optimization, with the ability to implement safe, cost‑efficient operational strategies.
• Valid driver’s license with an excellent driving record, and the ability to meet all organizational and insurance requirements; CDL preferred or ability to obtain one based on fleet needs.
• Hands on experience in budgeting, bookkeeping and reporting or willing to learn
• Proficient in Google Suite and open to learning new tools.
• Possess excellent crisis/conflict management skills and/or willing to learn.
• Desire to learn and grow professionally in the field of non-profit
• Engaging/responsive, and proactive communication
• Adaptable, collaborative, and self-motivated
• Establish and maintain highly professional effective working relationships with senior management, and other appointed officials, including staff, community and business leaders, donors, board members, and others encountered in the course of work
• Use a high degree of tact, discretion and diplomacy in dealing with sensitive situations and concerned groups and/or individuals
• Must be in agreement with and committed to upholding R.O.YO’s Motto Statement, and Statement of Values, as well as its stated Mission and Vision
• Education: A bachelor's degree in logistics, transportation, business, or a related field is often required.

The role involves working in an office environment but requires coordinating with field personnel. It may involve working, or being on call, during nights and weekends to handle emergencies or scheduling issues.

What We Offer as a Nonprofit Organization

At ROYO, we believe in giving as much as we receive. When you join our team, you become part of a community that values your time, energy, and heart. As a volunteer or team member, you’ll enjoy:

• Flexibility to work when it fits your life with clear communication around expectations.
• The chance to create real impact for youth, teens, and young adults across our programs.
• Remote work opportunities
• Training and mentorship from experienced leaders to help you grow personally and professionally.
• Volunteer hours and résumé-building experience that demonstrate your commitment to service.
• Reimbursement for approved travel or meals (for eligible roles).

Values We Live By

• Respect: We treat others and our communities with dignity and accountability.
• Open to Correction: We value honesty and feedback as essential to growth and ethical responsibility.
• Operational Excellence: We strive to deliver exceptional tools, skills, and training for all ROYO members, staff, and leaders.
• Teamwork: We collaborate with unity to achieve shared goals and empower others to join our mission.
• Striving for Success: We encourage pride, growth, and achievement for all members and leaders.

Restoring.Our.Youth.Organization Inc. is an equal opportunity employer. The above statements are intended to describe the general nature and level of work being performed. They are not intended to be construed as an exhaustive list of all responsibilities, duties, and skills required of personnel so classified.