Make Your Next Move Your Best Move

We love building teams of diverse, passionate people; all focused toward building something great. Being a part of Redwood means respect, hard work and fun, and nearly unlimited opportunities for serious career growth. Join Redwood and maximize your potential.

Why Work at Redwood?


We invest so much into our associates because at Redwood, our people drive success. And with diverse talent, we create perspectives that set us apart from the competition.


With double-digit growth since the beginning, we provide a dynamic environment where associates enjoy amazing opportunities for career growth. We’re expanding at our Chicago HQ and nationwide offices.


An amazing culture sits at our roots. Redwood teams thrive in an entrepreneurial environment where we reward hard work and demand fun. We’ve consistently been recognized as a top company to work for by several trusted organizations.

Perks & Benefits

Working with Redwood means learning from emerging leaders and experts, solving big challenges, and building innovative technology. It also means working with leadership teams who care about people as much as profits. A few more perks:


Medical, dental, and vision plans

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



Stack away future funds with our great 401k plan and matching program.


Competitive compensation

We offer competitive salaries plus eligible commission and/or bonus programs.


Ongoing career development

We’re committed to continuously investing your development and illuminating your career path.


Transit benefits

Chicagoland residents enjoy a tax-free transit benefit. Every dollar counts.


Employee referral bonus program

Refer a friend and receive a nice competitive bonus. Ka-ching.


Cell phone discount

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


Fitness membership discount

Get your workout on for less. Staying away from kitchen snacks is on you though.


Social responsibility

Help the community and feel great. We partner with charities and match employee contributions.



Food and fun

We throw onsite and offsite events like holiday parties and free lunches. See that roof? We’re raising it.


Employee events

Happy Hours, annual Redwood Games, and more to ways to eat, drink, and laugh with your colleagues.


Great music

Dance parties while you work? Yes. Practice your moves beforehand; we don’t play around.

Redwood Positions

Freight Exchange – Driver Application


Check out our full list of open positions. If you don’t see what you’re looking for, fill out our universal application and we’ll find something that fits.