Regional Vice President of Operations

Fountain; Chicago (IL); On-site; USD 200,000 - 210,000; Full time

Benefits offered by this job

Exceptional medical, dental, and vision insurance

401(k) with 4% employer match

Unlimited PTO

Paid holidays

Pet & legal insurance

On-the-job training and skills development

Job summary

A leading transportation firm is seeking a strategic Regional Vice President of Operations to oversee field operations across the U.S. This role includes managing Area General Managers and executing transportation services. The ideal candidate will have over 10 years of experience with at least 5 years in multi-site operations. Responsibilities also include resource planning and client relationship management. Competitive salary package including bonuses and health benefits is offered.

Qualifications

• 10+ years of progressive leadership experience in operations with 5+ years overseeing multi-site teams.
• Background in transportation or logistics strongly preferred.
• Experience managing large teams and achieving performance targets in client-driven environments.

Responsibilities

• Oversee day-to-day operations and align with organizational objectives.
• Supervise Area General Managers and location-level leadership.
• Develop and maintain operational procedures supporting scalability.

Skills

Strategic leadership

Operational management

Team management

Financial acumen

Communication skills

Problem-solving

Knowledge of DOT regulations

Customer relationship management

Education

Bachelor's degree in Business Administration, Transportation Management, or related field

Advanced degree preferred

Job description

Compensation $200,000.00 - $210,000.00/year

Job Description

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.

Key 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.

Qualifications

• 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.

We Offer

• Physical Health
• 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
• 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

WeDriveU is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment free of discrimination or harassment where thoughts and ideas of all employees are appreciated and respected. We value excellence and recognize that by respecting the diverse backgrounds, skills, and perspectives of our workforce, we will sustain a competitive advantage and remain an employer of choice. We also see diversity as more than policies; it is imperative for enabling us to attract, retain, and develop the best talent available.