The Amazon delivery van, with its signature smile on the back, slows to a stop. Its driver jumps out and steps quickly to the back of the vehicle. For a few moments, she readies several packages, then carries them to the front door of a home. Before leaving, she snaps a photo, which immediately prompts a notification for the customer that their order has arrived.
It’s a familiar scene for millions of Amazon customers every single day. But, what happens before the package makes it inside the delivery van?
Before customer delivery, boxes packaged at Amazon’s customer fulfillment sites travel via Amazon’s transportation network—called the middle mile--while delivery to your doorstep is referred to as the last mile. Packages leaving fulfillment centers are transported by Amazon’s freight and air networks, then land at one of Amazon’s sort centers, where they’re sorted by zip code before going to a delivery station.
Every day, thousands of incredible Amazon associates and partners who pick, pack, transport, and deliver, come together to create magical experiences for customers. Let’s meet some of the people who play a key role in transporting Amazon packages across the middle mile this holiday season.

Isaac Issa – Owner of Legacy Express Trucking, Inc.

Amazon employees who work on the middle mile, posing for the camera at work
Isaac Issa was a truck driver for four years before making the leap in 2012 to start his own company and recruiting some friendly faces to help him with his business journey.
“My brother-in-law works here, my little brother works in accounting, my cousins are dispatchers, and my sister does data entry. It’s a true family company,” he laughed. “I put in a lot of blood, sweat, and tears to start and grow this company, and we work from our heart. I hire within my family and great people within the industry. This collective team puts everything they have into this company, together. We all work as a unit.”
Issa’s company, Legacy Express Trucking, Inc., run out of Joliet, Illinois, operates more than 130 trucks and is one of the line haul service providers that Amazon partners with to transport cargo between Amazon sites. They began providing Amazon-dedicated capacity in 2018.
“Service, safety, and communication are our three core values. We are proud to partner with Amazon because they share those values,” Issa said. “Especially during COVID-19, I appreciate how seriously Amazon takes safety. Amazon looks at safety with a bright light.”
Issa explains how on Fridays, Amazon tenders freight loads to Legacy Express Trucking, so they use that day for planning. Typically, this means looking at where the freight loads are available and matching them with nearby available drivers.
“It’s like matchmaking,” he said. “We don’t like to force it, which is why we like working with Amazon. If our drivers want to be home at the end of each night, we find routes that work for them and their home life. Amazon allows our drivers to operate safely while ensuring their quality of life.”
Issa’s team uses Amazon’s Relay technology. This gives small freight carriers the flexibility to book and haul available Amazon loads that utilizes their free capacity. The Relay app has safely guided truck drivers over 175 million miles nationwide.
“The way Relay is designed allows us to take a look at our available loads on Fridays and plan accordingly for the following week. That’s so rare in the trucking industry. To me, it screams, ‘we care about you and your strategic planning just as much as we care about ours.’ It’s one of the biggest tools we have to coordinate getting our drivers home on time,” said Issa.
It’s no surprise that Issa’s steadfast focus on his drivers helps Legacy Express Trucking deliver strong results. In 2019, his company received the award for Fleet Management Excellence for the Midwest region.
“What makes us who we are? It’s passion. Passion in terms of our business model, how we attract drivers, and the transparency we offer our drivers. In turn, our drivers perform with the same passion. They love what they’re doing and know their work is appreciated.”

Chi Bernard – Amazon Air Ramp Process Assistant at Chicago Rockford International Airport

Amazon employees who work on the middle mile, posing for the camera at work
When Chi Bernard shows up for work at Chicago Rockford International Airport (KRFD) each morning, her first client is already there waiting for her—an Amazon Air 737-800 aircraft. On this specific day, she loads and unloads cargo from six different planes, up during the holiday season from the typical three planes she manages.
“My team loves being actively engaged on the ramp, so they’re excited,” Bernard said.
Bernard recently celebrated her fourth anniversary working at Amazon. A former fulfillment associate who helped launch a fulfillment center in Joliet, Illinois, she’s now responsible for loading cargo that fly in and out of Amazon’s air site at KRFD. She works with her team loading cargo, performs various checks, and communicates with the pilots about cargo load status and weight.
Amazon’s dedicated air network is a critical conduit to delivering packages across longer distances. It’s a feat that would be impossible without associates like Bernard managing the cargo load and unload process from start to finish. Bernard learned the complexities of managing air cargo and aircraft in just seven short months since transferring to this new role from a fulfillment center.
“I was part of the launch crew at the fulfillment center in Joliet, and I wanted to move up and move forward. I spoke with my manager, who explained that working for the Amazon Air business is an awesome opportunity for growth,” Bernard said “I wanted to get in on the ground floor of our KRFD operation, so I could witness the building grow. It’s been so exciting and fun to be a part of.”
Growth is exactly what drives Bernard professionally, too. While she was initially attracted to a job at Amazon because of the competitive pay and benefits, she’s learned throughout her time at the company that she has autonomy and support, driving her to pursue her passions within Amazon’s network.
“When I started working for Amazon, it was a job. Now it’s a career. The longer I am with Amazon, the more I realize the potential for growth opportunities here,” she said. “There are endless opportunity to do what you want at Amazon.”
The best part of this job during the holiday season?
“The team—it’s one of my favorite things about this job,” Bernard said. “No matter what team I’m on, or which shift I’m working, I always have a close, strong team of people around me.”
She explained her team’s morning ritual, which includes stretches before their shifts, and concludes with someone shouting, “ONE TEAM.”
“We all shout back in reply, ‘one dream!’ We do it every morning, but we also do it whenever we tackle an accomplishment. It’s our thing.”

Jasmin Honeywood – Learning Ambassador at an Amazon sort center in Illinois

Amazon employees who work on the middle mile, posing for the camera at work
Jasmin Honeywood thrives off creativity. Her artistic background keeps her busy creating art for her online shop in her spare time, and she’s illustrating a children’s book set to publish later this year. To fuel her creative passions, Jasmin also works as a Learning Ambassador at an Amazon sortation facility near Joliet, Illinois.
“When I graduated from university, I wanted to figure out a way to get into the field I studied by working on my passion projects while being able to earn a living,” she said. “That’s what led me to Amazon.”
A friend recommended her to Amazon, citing the company’s good pay and flexible work options. A year and a half later, Honeywood has moved into the role of Learning Ambassador. She coaches and teaches new hires at this sort center how to scan packages, manage the equipment that keeps packages moving throughout the site, and load and unload pallets of packages from trucks at the loading dock.
“As a Learning Ambassador, you’re basically the face of the warehouse for people who come in on Day 1 to learn about their new roles. People are often nervous, so my job is to reassure them and give them the tools and resources they need to do a great job,” said Honeywood, who colleagues can easily spot in her bright blue and yellow vest.
Amazon’s sort centers are a critical part of the company’s middle mile operations. Packages received from nearby fulfillment centers are processed and sorted at these sites, then transported to Amazon’s last mile delivery stations or other carrier partner sites, like the local post office, before customer delivery. Honeywood’s team is preparing for a busy holiday season ahead.
“This is the time of year when I plan to ramp up my teaching efforts as a Learning Ambassador. We’re preparing for new hires to come in and are ready to help them out,” she said.
Honeywood knows this experience well. She remembers her early days at the sort center, where she learned the ropes.
“Once you get past that first month of learning, people will start to approach you to try different things and explore new opportunities,” said Honeywood. “It wasn’t on my mind to become a Learning Ambassador, but now that I’m doing it, I feel like I’m making a difference for the other people working here.”
Those close personal connections have had an impact on Honeywood, too.
“When I was just starting, managers would come up to me on the floor to tell me I was doing a good job, have a conversation, and keep up-to-date on my growth. Those moments are great when you’re working in a warehouse with hundreds of other people. I enjoy those little moments,” she said.
Jasmin’s passion for teaching and thinking creatively shows no boundaries and reinforces the driven, passionate person at her core. She’s proud to have a job that allows her to grow professionally while allowing her the flexibility to pursue her artistic pursuits in her free time.