At Arrive Logistics, we believe a comprehensive training experience is the foundation of success. To support this belief, we have an entire team dedicated to the creation and execution of our robust training program. We are so excited to add a Bootcamp Trainer to our Chicago team who can leverage their previous sales experience to mentor new sales reps as they progress during basic training! This role represents an opportunity to take ownership of each rep’s performance & add value to our existing training program through hands-on mentorship & development. If you have a background in freight sales, a proven ability to get in the trenches, and a passion for coaching others, then we cannot wait to meet you!


  • Lead the “Bootcamp” portion of Arrive’s Development Program, a 3-week session during basic training.
  • Ensure learning objectives, activities, and comprehension tests are successfully executed & in alignment with the company’s goals.
  • Continuously evaluate & improve your portion of the training program as the company evolves.
  • Work with the Training Specialist to prepare for each start date in the Chicago office.
  • Prepare new hires for their transition to the sales floor and work with sales leaders to ensure a seamless hand-off.
  • Lead continued education opportunities in our Chicago office.
  • Lead technology engagement opportunities in our Chicago office.
  • Manage & encourage engagement opportunities between trainees and leaders across the business during their training program.
  • Serve as a resource for the Learning & Development team in other areas of Arrive’s Development program, as needed.


  • A bachelor’s degree in a relevant field of study, preferred.
  • 1+ year of customer-facing sales experience at a third party logistics provider and/or transportation company.
  • Flexible & solutions-oriented. In this environment, things change quickly and we need someone who can roll with the punches & provide creative solutions.
  • The ability to challenge reps & hold them accountable through goals & metrics.
  • A proven knack for building productive relationships with a wide spectrum of people. You will be working with leaders across the business, so collaboration is key.
  • Unafraid to get their hands dirty! You can pick up the phone and lead by example.
  • A calm, patient demeanor as our reps navigate their first few weeks at Arrive.
  • A “let’s go” attitude – once you meet us, you’ll see what we mean!


  • Make an immediate impact on a growing team.
  • Working the heart of downtown Chicago, IL!
  • Earn a competitive compensation package.
  • Collaborate alongside experts in the logistics industry.
  • Take advantage of excellent benefits, including health, dental, vision and life coverage.
  • Invest in your future with our matching 401k program.
  • Leave the suit and e at home; our dress code is casual.
  • Eat for free on Fridays…lunch is on Arrive!
  • Sweat it out – we have an on-site gym!
  • Recharge your batteries at our fully-stocked caffeine bar.
  • Soothe aches and pains with our monthly in-office massages!

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