Brittany Caskey, chief commercial officer at DP World, leads strategy and capability development across the company’s freight forwarding and contract logistics divisions. In this role, she is spearheading an ambitious growth agenda aimed at doubling revenue and EBITDA between 2025-2027, positioning DP World as a leading force in end-to-end supply chain solutions across the region. Since joining DP World, Caskey has continued to break new ground, transforming the Americas region’s commercial strategy by bridging operations across North and South America and by spearheading the separation of logistics vs. terminal business lines to sharpen focus on each. In just her first six months, she led her team to record commercial results, proving that her success formula works in a new environment as well. She also uses her platform as a senior leader to mentor and elevate other women in the industry, making inclusion and excellence go hand-in-hand.
With two decades of experience in the logistics industry, Caskey began her career at UPS giving tours of its largest contract logistics campus in Louisville, Ky., before advancing into a sales role focused on warehousing and distribution solutions for high-tech, industrial, and retail clients. In 2016, she was promoted to lead the North America sales team, including Canada and Mexico, where she introduced new go-to-market strategies to penetrate untapped verticals, resulting in sustained double-digit growth. Her success led to a global role in 2020, where she assumed leadership of UPS’ global logistics and distribution sales and customer solutions organization, where she drove global sales alignment, standardized customer engagement practices, and spearheaded cross-regional collaboration to deepen account penetration. She maintains deep experience working with companies ranging from start-ups to Fortune 50 enterprises, partnering at the C-suite level to reimagine end-to-end supply chains. Her expertise spans sales strategy, solutions development, new business acquisition, and customer retention.
Caskey’s cross-functional and cross-regional background is a key driver of her out-of-the-box thinking, having worked in nearly every corner of the supply chain – from ground-level warehouse operations to C-suite strategy. She’s seen the inefficiencies of siloed warehousing, envisioned a more flexible multi-client warehouse model, turned a traditional single-tenant operation into a nimble, revenue-optimizing service and crafted creative contract structures that adapt to seasonality. She also fosters a “One Americas” approach, recognizing that connecting the North and South American logistics networks could unlock hidden value.
Known as “The Logistics Lady,” Caskey defined four pillars of career and life success (called SHIB: Success, Happiness, Influence, Balance) and encourages industry peers to strive for profit and purpose.
Caskey was named the overall winner of the Trailblazers category for this year’s Women in Supply award, presented by Food Logistics and Supply & Demand Chain Executive, and sponsored by Let’s Talk Supply Chain and Blended Pledge program.
Marina Mayer, editor-in-chief of Food Logistics and Supply & Demand Chain Executive and co-founder of the Women in Supply Chain Forum, sat down with Caskey to learn more about her “outside-of-the-box” leadership, why mentorship matters and what it takes to experience the full spectrum of the supply chain.
Food Logistics and Supply & Demand Chain Executive: Let’s first talk about you. Tell me a little bit about yourself and your journey to get to this current stage in your career?
Brittany Caskey: My journey into logistics was unexpected. I had originally planned to go into medical device sales, but at a job fair after college, I met a recruiter from UPS and that moment changed everything. What started as giving customer tours at a major logistics campus quickly evolved into a career I fell in love with. The fast pace, the problem-solving, and the ever-evolving nature of the supply chain drew me in, knowing that our work powers global trade, the clothes we wear, the cars we drive and the medicine we need.
At just 22, I was given the opportunity to join a sales team, and that role ignited my passion for sales and leadership. Over the years, I climbed the ranks at UPS, eventually overseeing North America and then leading the global logistics and distribution sales and solutions team. Each new challenge helped me grow, enabling me to join DP World where I now serve as chief commercial officer, logistics for the Americas. My path has been shaped by curiosity, resilience, and a drive to continually improve, not just for myself, but for the teams I lead. At DP World, I've found a world of opportunities where I'm supported to grow at every step of my dynamic journey.
Food Logistics and Supply & Demand Chain Executive: Your journey began with UPS, where you drove over $570 million in new business revenue and sustained double-digit topline growth. Now at DP World, you transformed the company’s U.S. commercial strategy by bridging operations across North and South America. Walk us through other achievements.
Caskey: Some of the most meaningful achievements in my career go beyond the numbers. One defining moment was stepping into my first leadership role at UPS. I was leading a team of experienced professionals; many of whom had been in their roles longer than I had. Earning their trust required more than a title, it took humility, consistent performance, and a commitment to leading by example. That experience taught me how to lead with both confidence and empathy.
At DP World, I’m especially proud of the cultural transformation we’re seeing. We’ve worked hard to create a more inclusive and empowering environment where everyone is welcome. Throughout my career, I’ve seen how diverse perspectives lead to stronger ideas and better outcomes, and it’s rewarding to see that mindset embraced across the organization. With more than 115,000 people across 79 countries, being part of this team of amazing people means you're part of something bigger.
I’ve also learned the importance of balance. After experiencing a heart attack in my mid-30s, I had to rethink how I approached both work and life. That experience shaped me into a more resilient and compassionate leader. It’s also why I’m deeply committed to mentorship, helping others not just succeed but do so in a way that’s sustainable and grounded in purpose. I'm grateful to work for a company that cares about creating meaningful change in the world, with sustainability, safety and economic growth at the heart of our mission.
Food Logistics and Supply & Demand Chain Executive: According to your application, you’ve worked in nearly every corner of the supply chain. Tell us more, and detail how these experiences have helped you advance in the supply chain space.
Caskey: From warehouse floors to boardrooms, I’ve truly experienced the full spectrum of the supply chain. Early in my career, I learned the nuts and bolts – literally – by learning operational processes in warehousing and distribution. I’ve led both customer-facing sales teams and behind-the-scenes solutions architects. I’ve been involved in building business plans, developed commercial strategies, and shaped digital transformation projects.
That diversity of experience allows me to think holistically and connect the dots others might miss. For example, because I’ve seen the pain points of siloed operations, I know how powerful integration can be – whether that’s through multi-client warehousing or inter-regional collaboration. Working with pioneering technology to make trade smarter, safer, and more sustainable has been at the core of my approach. It's this end-to-end perspective that helps me bring innovative, customer-centric solutions to the table. The skills I've gained from hands-on experience to cutting-edge technology have been invaluable, and I'm proud to work for a company that invests in training and development at every level.
Food Logistics and Supply & Demand Chain Executive: You’re also celebrated for your “outside-of-the-box” leadership. In fact, you’ve fostered a “One Americas” approach. Why is this so important, especially in today’s landscape?
Caskey: In logistics, traditional thinking often leads to siloed operations – each country, each service line operating independently. That’s not how the world works anymore. Customers are global, their needs span regions, and they expect seamless, consistent service.
The “One Americas” approach is about breaking down those barriers and treating North and South America as one integrated market. I introduced cross-regional strategy sessions and opportunity-sharing frameworks so our teams in Brazil, Canada, the U.S., and elsewhere could collaborate in real time. But it’s also about building a shared culture. At DP World, we say "we're one team" and I take that to heart. We believe in teamwork, respect, and safety; no one succeeds alone. No matter where you sit – in Miami, São Paulo, or Vancouver – you’re part of something bigger. You’re not just doing a job; you’re helping keep trade flowing for the world.
Outside-the-box thinking is also how we solve internal challenges. For instance, instead of building massive warehouses for single tenants, we’ve implemented flexible, multi-client models that drive revenue and adaptability. Innovation isn’t just about tech; it’s about reimagining how we work. When you work with the best – our people are experts in their field, driving innovation and shaping the future of trade – these breakthrough solutions become possible
Food Logistics and Supply & Demand Chain Executive: You also value coaching and mentorship. What specific coaching and mentorship programs are you involved in? And what is coaching and mentorship so important for any supply chain leader?
Caskey: Mentorship is personal to me. I’ve benefitted tremendously from mentors who saw potential in me even when I doubted myself. At UPS, I lead a variety of women in leadership initiatives and founded recognition programs specifically for women in logistics. I now coach emerging leaders through “The Logistics Lady,” my personal coaching platform that promotes Success, Happiness, Influence, and Balance – what I call SHIB.
Mentorship matters because this industry can be tough to navigate, especially for women. By sharing our experiences, we create a ripple effect. Coaching helps leaders develop not just skills, but confidence. It shows them what’s possible and gives them the tools to get there. I'm proud to be valued for the work I do, with benefits that help me thrive in and outside of work, and I want to ensure others have those same opportunities to flourish.
Food Logistics and Supply & Demand Chain Executive: The Trailblazers category honors female leaders who continue to pave the way for future females in logistics. What advice do you have for other female professionals in the supply chain space?
Caskey: Three things:
First, find your voice. Don’t be afraid to speak up. Early in my career, I learned that using your voice – even when it shakes – builds credibility and creates space for others.
Second, facts over feelings. In tough rooms, data speaks louder than opinions. Let your performance be your proof.
Third, be brave, not perfect. Women often feel they need to check every box before going for the next opportunity. You don’t. Growth happens when you stretch, when you bet on yourself, even when you’re not 100% ready. Remember, you have a world of opportunities ahead of you. Shape your dynamic journey and know that you'll be supported to grow at every step.
Food Logistics and Supply & Demand Chain Executive: What are some things not addressed above that would be pertinent to share with our readers detailing your strengths, achievements, overall goals, etc.?
Caskey: I’m proud of the numbers, but even prouder of the people. I’ve led teams to record-breaking sales, but what stays with me are the stories: the person who gained confidence, the young woman who stepped into leadership, the team that rallied during a tough quarter.
Ultimately, my goal is to make logistics more human. To build high-performing teams, yes, but also to build environments where people thrive, where women feel seen and heard, and where success doesn’t come at the cost of happiness or health. At DP World, we're not just shaping the future of trade, we're creating meaningful change in the world. That’s what being a trailblazer means to me.
