Regional Vice President of Operations at WeDriveU – Chicago, Illinois

WeDriveU is seeking a strategic and results-oriented Regional Vice President of Operations to lead and manage field operations across our nationwide transportation network. This executive-level position is responsible for overseeing Area General Managers and ensuring the successful execution of transportation services across all client locations. The VP of Operations will play a pivotal role in driving operational performance, standardizing best practices, and delivering exceptional service quality to our clients.

• Provide strategic leadership and oversight of day-to-day operations across all markets, ensuring alignment with organizational objectives and client commitments.

• Directly supervise and support Area General Managers and, where necessary, location-level leadership, fostering a culture of accountability, safety, and continuous improvement.

• Develop, implement, and maintain operational procedures and performance standards that support consistency, compliance, and scalability across regions.

• Monitor key operational metrics (e.g., on-time performance, staffing levels, service quality, safety compliance) and lead action plans to address areas of opportunity.

• Collaborate with cross-functional departments including Human Resources, Safety, Compliance, Finance, and Talent Acquisition to support operational needs and initiatives.

• Drive resource planning and optimization efforts, including workforce deployment, fleet management, and training strategies.

• Serve as the primary escalation point for complex operational issues, partnering with field leadership and corporate teams to resolve challenges effectively.

• Lead talent development efforts across the operations organization, identifying high-potential leaders and establishing pathways for growth and succession.

• Conduct regular site visits and operational reviews to ensure compliance with contractual obligations, internal standards, and industry regulations.

• Establish working relationships and ongoing partnerships with all clients that are serviced by operations in your area.

• Contribute operational expertise where required in bid model development and ongoing labor negotiations.

• Participate in strategic planning and budgeting processes, managing operational P&Ls and ensuring financial targets are met or exceeded.

• Bachelor's degree in Business Administration, Transportation Management, or a related field; advanced degree preferred.

• Minimum of 10 years of progressive leadership experience in operations, with at least 5 years overseeing multi-site or regional teams.

• Background in transportation, logistics, or related service industries strongly preferred.

• Demonstrated success managing large teams, executing standard operating procedures, and achieving performance targets in a fast-paced, client-driven environment.

• Strong financial acumen, with experience managing budgets and operational forecasting.

• Exceptional leadership, communication, and problem-solving skills.

• Knowledge of DOT regulations, safety practices, and union environments is a plus.

• Experience with both union and non-union workforces.

• Ability to travel regularly to support regional teams and operational needs.