CEO Spotlight With project44

by Drew Beechler - Director of Marketing

An Interview with Jett McCandless, CEO of project44

This article is part of High Alpha’s CEO Spotlight series. We regularly sit down with High Alpha portfolio CEOs and leaders to dig into their business, team, and story. You’ll get an inside look at the companies in our portfolio and their incredible leaders and teams.

Last year, we had the privilege to invest in project44’s Series B funding alongside an incredible group of investors, including OpenView, 8VC, Emergence Capital, and Omidyar Technology Ventures. Later in 2018, they also announced another $45M in funding to accelerate their global expansion.

I recently had the opportunity to sit down with project44’s CEO Jett McCandless to talk more about project44, his entrepreneurial beginnings, and lessons learned along the way.

Drew: Give us the quick project44 pitch and what you do.

Jett: project44 connects, automates, and provides visibility into key transportation processes to accelerate insights and shorten the time it takes to turn those insights into actions.

D: How did you find yourself falling into the logistics and transportation industry?

J: My first logistics job was over 20 years ago in P&D Dispatch at Roadway Express in Portland. My job was to answer the phone, record shipment information, and input it into another system. Quickly, I realized that the only reason this job existed was because of poor data connectivity. In the various roles throughout my career — linehaul supervisor, outbound dock coordinator, national sales manager, principal — those same patterns of inefficiencies, poor data, and disappointing customer experience continued. The technology side dovetailed into that fairly naturally. These costly inefficiencies inspired me to start a technology company that would digitally transform the manual processes that were holding back our global supply chains.

D: How did those experiences evolve into the idea for project44?

J: Every object that we use in our daily lives was at one time shipped on a boat, train, plane, and/or truck to get to you. Yet everyone involved will tell you that this process is broken. To move a single pallet of goods from origin to final destination you are seeing a handoff between an average of ten companies and 30+ individuals as the products clear customs, cross borders, and change vehicles to ultimately get to the end consumer exactly when that end consumer needs it.

project44 was started to create a better, more accurate, and more reliable way to ship goods and reduce the complexity of the global freight industry through technology. I saw the transformative powers that modern technologies were having in other verticals, and I knew they could have a profound impact on the inefficiencies I was seeing in transportation and logistics. That’s actually where our name, project44, came from. Highway 44 was the first bypass to the historic Route 66. When the country’s needs grew to be too much for Route 66, Highway 44 was built to usher in the new era of efficiency. That’s what we’re digitally doing within logistics technology.

D: Where did you first develop your entrepreneurial itch?

J: I can’t really remember a time where I didn’t have an entrepreneurial itch. The moment when it became my path in life was after leaving GlobalTranz, a logistics provider with gross annual revenues of $1.1 billion. After probably 25 job interviews and some really compelling offers, something just didn’t feel right. I thought to myself, “Should I take a comfortable, secure job, or could I build something better that is going to redefine how the entire world moves product?” I knew the answer immediately. Building companies has been fun, challenging, and rewarding. The more we do, the more I want to continue. At the end of the day, it’s about improving the industry and creating opportunities for talented people. Who wouldn’t want to do that?

D: What are you most excited about in your upcoming product roadmap?

J: We’re working on some incredible things that will have a massive impact on a global scale! I get the most excited about the projects that bring us closer to connecting the organizations, transportation carriers, and systems involved in the supply chain and empowering these leaders with advanced visibility. Right now, our next steps are rolling out our advanced Ocean visibility solution and continuing a European expansion. Those two initiatives fill in key pieces of this global puzzle. They make the global supply chain more connected and manageable, which brings us closer to our vision.

D: What has been one of your proudest accomplishments as a company over the past year?

J: Our growth over the last year has been incredible. We have experienced incredible bookings growth, made over 3 billion annualized API calls, and built a network of over 175,000 global transportation carriers.

We are fully committed to hiring the right people, even if it takes more time and effort than hiring somebody else. A great team produces great results, and we’re heavily invested in hiring, retaining, and growing talent. To strategically move the company forward, we are continuously looking to unearth new opportunities (new benefits, improved office space, team engagement strategies, mentorship programs, leadership training, collaboration tools, etc.) that further align our recruitment and talent management strategies with future growth.

D: Outside project44, how do you recharge, where do you spend your free time, or what are you passionate about?

J: I love the outdoors. There is an incredible, calming effect that comes with going out into nature and doing something active. It clears my head and resets me so I’m able to better focus on my work. I take every chance I get to spend time outside, away from the city. Some of my favorites are skiing, mountain biking, wakeboarding, and hiking!

D: What advice would you have for other founders and CEOs of high-growth startups?

J: Rely on your personal experience and expertise for direction, and hire the best people in the world to do the things that need to be done in order to scale. Your personal well of knowledge is going to guide the ship, but a big part of success in hyper-growth startups is realizing you can’t do everything on your own and finding the best people possible to come in and help you scale. If you have a great idea, a talented team, and a strong work ethic, you’ll be successful.

D: If people are interested in learning more about project44 or joining the project44 team, where should they go for more information?

J: If you want to learn more about our advanced visibility platform, check out our website! If you’d like to schedule a demo to see how our visibility platform can enable cost savings and efficiency for your business, email us at If you’re interested in Chicago’s hottest tech company, check our jobs page here. Also, don’t forget to follow us on twitter @FreightPipes.