Our employees drive our success.
You can too.

Learn. Grow. Have Fun.

The transportation and logistics industry is vast, but what makes Redwood stand apart from other logistics companies is our full range of services and solutions. This means you have virtually unlimited opportunities for growth no matter where you are in your career.

When you work at Redwood, you’ll work closely with industry experts, emerging leaders, and innovative technologies.

Last but not least, Redwood is a lot of fun. But don’t take our word for it.

Why work at Redwood?

Careers People


People drive our success. That’s why we invest so much into our people. Our diversity of talent creates a perspective that sets us apart from our competition.

Careers GrowthGrowth

We have experienced double digit growth since our inception in 2001. We provide a dynamic environment where associates enjoy unparalleled opportunities for growth. We continue to expand both in our Chicago headquarters and throughout our nationwide branch office network.



Whether you’re entry-level or executive-level, we encourage sharing of best practices and new ideas to steer Redwood in the right direction.



Our teams thrive in an entrepreneurial environment where hard work is rewarded and fun is demanded. We’ve been consistently recognized as a top workplace by several trusted organizations.

Meet our people


"We have fun making our customers great"

- Matthew Hutter, Senior Carrier Sales Representative

"What we're doing is making a difference"

- Jason Hartwig, Manager - SCS Operations

Meet our Team

Andrea Alaimo Andrea Alaimo

Maria MarinezMaria Marinez

Allie HoganAllie Hogan

Perks & Benefits

Medical, Dental & Vision Plans

We offer comprehensive medical, prescription, dental, and vision options.


We offer a 401k plan with matching program.

Competitive Compensation

Including eligible commission and/or bonus programs.

Ongoing Career Development

Dedicated to illuminating your career path with cutting-edge process and technology.

Transit Benefits

Chicagoland residents can enjoy a tax-free transit benefit.

Employee Referral Bonus program

Refer a friend and receive a competitive bonus.

Cell Phone Discount

Enjoy up to a 20% discount with your qualified Verizon plan.

Fitness Membership Discount

Get your workout on for less.

Social Responsibility

Redwood partners with a number of charities and provides employer match as well contributions to show our support.

Food and Fun

The company often sponsors both on-site and off-site social events like holiday parties and free lunches.

Happy Hours

Have a drink on us at one of our many company sponsored events.

Great Music

Dance parties while you work.

Featured Positions

Positions by department

Looking to drive? Become a Freight Exchange Driver

Your Next Generation Freight Management

Our next-generation model specializes in moving freight throughout North America, backed by our vast carrier network, logistics expertise, and industry-leading proprietary technology.

Redwood Supply Chain Solutions uses sophisticated technology, flexible outsourced freight management and deep supply chain expertise to help middle-market companies excel in their competitive landscape.

Simplify your transportation process and improve your service to customers, while reducing your transportation spend to add to your bottom line.

We leverage innovative platforms and the industry’s brightest team to provide next generation technology solutions. That might mean more supply chain control, cost savings, faster or more continuous innovation – or all this and more.

Our asset-based truckload company provides critical capacity solutions to our diverse customer base throughout North America.

Our asset-based warehouse and distribution company specializes in high velocity, value-added supply chain solutions for the complex Southern California and Chicagoland markets.