Amazon Freight’s Dedicated Transportation Consultants serve as a proactive, personalized resource for shippers, to ensure their freight moves reliably. Meet Bobby Bailey, he helps his customers’ freight orders get to their destination as planned, while also looking around corners to help solve customer pain points—sometimes even pain points they hadn’t realized were heading their way. We asked him about his background and current account management role at Amazon Freight.
Q: What is your role and what does it entail?
I’m a Dedicated Transportation Consultant for Amazon Freight. I work with customers who book through freight.amazon.com, primarily shipping inbound less-than-truckload (LTL) and full truckload (FTL). I help them resolve problems, find solutions for their freight, and lock in optimal rates. I like to tell my customers: “Give me a 20-foot wall, I’ll give you a 30-foot ladder.”
Q: How did you get started in the transportation industry?
I’ve always been fascinated by everything that goes into synchronized logistics, that’s what drew me to supply chain management. I studied supply chain management at Arizona State, a top three program for that major. After graduation, I worked across several warehouse and distribution jobs. I was recruited by Amazon, and it felt like stepping into the future, the automation and fulfillment center technology were unlike anything I’d seen in past roles. I’m still excited to be part of a company that’s cutting edge and always raising the bar for customers.
Q: What is one thing you love about your role?
I started my Amazon career in operations before moving into sales three years ago. That transition taught me something important: I love being close to the end customer. In my role, it’s all about finding the right moment to connect with a customer and being a resource they can count on.
Q: How has your experience helped your customers?
Something that makes me a little different than my peers: I have experience as an Amazon seller. Back in 2016, I started selling spiced nuts on Amazon. They’re a popular snack in Georgia, where I’m from.
That experience gave me real credibility with sellers shipping inbound to Amazon. I’ve been in their shoes; I understand the frustrations and challenges of split shipments and consolidating freight efficiently.
My firsthand experience working in warehouses gives me a different lens when a customer’s load doesn’t show up. I can quickly identify what happened, explain it clearly to the customer, and share those learnings with our tech teams. I’ve also worked in recoveries (urgent freight assignments that need to be picked up immediately to replace a delayed, cancelled, or broken-down shipment) and on-demand freight procurement, so I bring a lot of cross-functional perspective to every customer conversation.
Q: How do customers engage with you?
I always start with what the customer needs. I’ve found that they want someone who’s genuinely receptive, responsive, communicative, and easy to reach. I love visiting customers in person. Seeing their warehouses and understanding their operations firsthand helps me deliver more value to them. They might tell me about five pain points, but when I walk their floor, I often spot six, seven, or eight that we can solve together. That’s one of the most rewarding parts of this job, and I think it shows customers that I’m serious about supporting them.
One example: a customer was shipping small pallet loads daily, which was more expensive than other options and created scheduling headaches. I introduced them to our inbound LTL drop trailer program, which lets them load pallets into a trailer on their own timeline until it’s full—then we pull it on a consistent day each week. It simplified their outbound planning and reduced costs by consolidating shipments. That solution came directly from asking the right questions.
Q: The transportation space can be stressful, especially during peak season. What do you do to unwind?
Since I live in Atlanta, this might surprise people, but I love ice skating.
My daughter turned seven in March, and she’s passionate about figure skating. I realized the best way to support her was to join her, so I did. When I was younger, I worked as a roller-skating DJ, so lacing up my own skates felt natural.
When I’m not at the rink, I’m probably reading a personal development book. My favorite is Dale Carnegie’s How to Win Friends and Influence People, it’s a compassionate, listening-first approach that honestly applies just as much to freight as it does to life.
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