Regional Vice President of Operations

WeDriveU•Chicago, IL

About The Position

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.

Requirements

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

Nice To Haves

Knowledge of DOT regulations, safety practices, and union environments is a plus.
Experience with both union and non-union workforces.

Responsibilities

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.

Benefits

Exceptional Medical, Dental, Vision, and Life Insurance benefits
Competitive compensation packages—including base salary, bonus, and benefits—along with unlimited PTO.
401(k) with 4% employer match
Financial Wellness Tool
Commuter Benefits
Employee Assistance Program (EAP)
Unlimited PTO
Paid holidays
Pet & Legal Insurance
On-the-job training and skills development
Internal transfer opportunities for career growth
Benefits vary by position and location