Regional Manager – Dedicated Driver

Airspace; Wilmington (DE); On-site; USD 68,000 - 83,000; Full time

Job summary

Airspace is seeking a Regional Manager to lead a network of Dedicated Drivers, including W-2 and 1099 staff, and to support drivers while meeting customer needs. The role emphasizes hands-on leadership, driver development, and strong partnerships with customer stakeholders.

You will train, coach, and evaluate drivers, manage performance improvement plans, and travel up to 50% to regional locations to strengthen relationships and ensure service quality.

Qualifications

• 3+ years of experience in transportation or logistics operations.
• Proven experience in driver or workforce training, coaching, and performance management.
• Demonstrated ability to build and sustain strong relationships with both frontline workers and customers.
• Willingness and ability to travel up to 50% of the time, including regional driving, domestic flights, and overnight stays at customer site locations.
• Comfort operating in a field-based environment, with the ability to manage responsibilities effectively while traveling.
• Strong communication skills (verbal and written).
• Positive attitude with an ability to connect with drivers and customers alike.
• Detail-oriented and skilled in active listening.
• Ability to partner with cross-functional teams to drive positive outcomes.
• Action-oriented and comfortable in a fast-paced environment.
• Experience working in environments with rigorous process adherence.

Responsibilities

• Lead onboarding and ongoing training programs to ensure drivers have the knowledge, tools and skills to perform at a high level.
• Provide coaching and direct feedback to drivers to foster continuous improvement and accountability.
• Develop and implement performance improvement plans, with quarterly retraining and reviews.
• Monitor driver performance metrics and identify trends, risks, and opportunities for development.
• Build and maintain a healthy driver base across geos and customers.

Skills

Driver training

Coaching

Performance management

Relationship building

Travel coordination

Clear communication

Problem solving

Time management

Cross-functional collaboration

Tools

CRM systems

Job description

Company Introduction

Airspace is a tech-enabled freight forwarder that is redefining how the world’s most critical packages are delivered. Headquartered in Carlsbad, California, Airspace has employees who are based around the world. Our European headquarters is in Amsterdam, The Netherlands. As a recognized leader in AI and machine learning, our team leverages data and patented technology to coordinate logistics across a global network of drivers and airlines. Our goal is to deliver those packages that are truly mission-critical in a way that is faster, more transparent, more secure, and more accountable than ever before. The items we deliver range from organs for transplant, to parts for critical machinery including grounded aircraft and highly sensitive components such as semiconductors. Airspace has been rated one of America’s best Startup Employers and listed as one of CNBC’s Disruptor 50 companies. Airspace has the support of leading investors such as Telstra Ventures, HarbourVest Partners, Defy Partners, DBL Partners, and Scale Ventures. To date the company has raised more than $140m. The company is growing rapidly and serving more places around the world than ever before. We are looking for passionate, motivated individuals who want to make an IMPACT every day to help us execute on our mission of reshaping the world of time‑critical logistics.

What is the "Dedicated Driver" Service?

Airspace partners with leading U.S. Medical Device companies to ensure life‑saving equipment is transported safely and securely to hospitals across the country. Our dedicated drivers are the critical link between warehouses and operating rooms, delivering essential surgical tools in real time. Every delivery matters. Every driver represents Airspace.

Compensation

$75k annual salary + 10% bonus target

About the Role

As a Regional Manager, you will be responsible for managing a network of Dedicated Drivers, which may include W-2 employees, 1099 contractors, or a combination of both. You will support drivers directly, ensure customer needs are met, and own execution of tactical initiatives to deliver top‑quality service. You will be a hands‑on leader who invests deeply in driver development and cultivates strong, trust‑based relationships with both drivers and customer stakeholders.

What You’ll Do

Driver Training, Coaching & Performance Management

• Lead onboarding and ongoing training programs to ensure drivers are equipped with the knowledge, tools, and skills to perform at the highest level
• Provide consistent coaching and direct feedback to drivers, fostering a culture of continuous improvement and accountability
• Develop and execute individualized performance improvement plans, conducting quarterly re‑training sessions and regular performance reviews
• Monitor driver performance metrics closely and proactively identify trends, risks, and opportunities for development
• Build and maintain a healthy, engaged driver base across assigned geos and customers

Customer & Driver Relationship Building

• Serve as a primary point of contact for customer accounts, working collaboratively with Account Management to cultivate strong, long‑term relationships with customer POCs through regular communication and in‑person engagement.
• Travel up to 50% of the time to regional customer site locations; including regional driving, domestic flights, and overnight stays to maintain visibility and deepen partnerships
• Conduct in‑person market performance reviews at customer sites to assess service quality and proactively surface improvement opportunities
• Build trusted relationships with drivers through daily interactions, check‑ins, and onsite visits, ensuring they feel supported and set up for success
• Coordinate and manage change requests in close partnership with both drivers and customers, ensuring smooth and timely execution

Operations & Process Ownership

• Provide direct support to drivers on tactical problems that arise
• Proactively partner with the Revenue team to action driver feedback and develop clear resolution plans
• Manage driver rate establishment, billing, and payment execution
• Actively govern work through formal documentation and identify opportunities to streamline processes
• Partner with leadership to identify process gaps and take swift action to close them

What We’re Looking For

• 3+ years of experience in transportation or logistics operations
• Proven experience in driver or workforce training, coaching, and performance management
• Demonstrated ability to build and sustain strong relationships with both frontline workers and customers
• Willingness and ability to travel up to 50% of the time, including regional driving, domestic flights, and overnight stays at customer site locations
• Comfort operating in a field‑based environment, with the ability to manage responsibilities effectively while traveling
• Strong communication skills (both verbal and written)
• Positive attitude with a natural ability to connect with and motivate drivers and customers alike
• Detail‑oriented and excels at active listening
• Ability to partner with cross‑functional teams to drive positive outcomes in service
• Action‑oriented and comfortable in a fast‑paced environment
• Experience working in an environment where work activities require rigorous process adherence
• Strong time‑management skills and multitasking ability
• Solution mindset: Demonstrated ability to "own" problems end‑to‑end

Core Values

• We are One Team. We believe we all accomplish more when we are working together.
• We make an Impact. We are determined to have a positive influence on our environment, our customers, our industry, and our world.
• We are Passionate. We care deeply about our mission and are not afraid to raise the bar.
• We are Transparent. We pride ourselves on having open, honest, and sincere communication with our team and customers.
• We are Innovative. We never settle and are always striving to improve our product, service, and ourselves.

Airspace is proud to be an Equal Employment Opportunity and Affidative Action employer. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Additionally, Airspace participates in the E-Verify program for all locations.

A friendly reminder: Airspace will only contact candidates from an @airspace.com email, a no-reply notification from [e-mail], or a verified LinkedIn profile. We never request fees or sensitive personal/financial information during recruiting. If something seems suspicious or feels off, please reach out to us at [e-mail] before responding.

For this role the acquisition of recruitment agencies is not appreciated, thank you for your understanding.