Little Caesars Pizza

Jim Mason’s extensive experience in software engineering and IT leadership is instrumental in driving technological advancements in the food and retail industries. His expertise spans eCommerce and store systems technology, including kiosk and café hardware, menu master data management, catering solutions, loyalty programs and software development. He has played a key role in optimizing digital and instore experiences through seamless system integrations and innovative technology solutions.

Insights about Professional Journey and Current Responsibilities

I've been fortunate in my career. I retired from the Air Force after 20 years as a loadmaster, spending 17 of those years flying on C-5s. Just before retiring, I transitioned into IT, which set the stage for my next career path. After leaving the military, I joined SBC (now AT&T), where I worked in a data center, gaining extensive experience with data center technologies. I later took on project ownership roles and played a key role in rewriting a major customer-facing application.

After six years at AT&T, I moved to Enterprise Rent-A-Car, where I led the Enterprise Maintenance and Support Group (EMSG). This team was responsible for ensuring 24/7 system availability and stability on a global scale. I spent three years there before moving to Express Scripts, which later became Cigna. During my time there, I managed mid-range operations and oversaw release management across several mergers and acquisitions. When I joined, the company was ranked Fortune 134 and by the time I left, it had risen to Fortune 11.

 Adopt, adapt and continue growing with AI—it’s not just a trend, but a foundation for the future. It is important to embrace change and leverage innovation to enhance the customer experience 

After that, I joined Panera Bread, where I led the implementation of kiosks—taking the project from deployment of 6,000 kiosks across cafes to development of the next generation. In addition to kiosks, my team and I handled all in-store technology, including payments, menus, catering systems and websites. I emphasize “we” because everything I accomplished was as part of a dedicated team.

I left Panera in early 2020, just before COVID and transitioned into election software, working with a company based in St. Louis. I was there for about 13–14 months before reconnecting with some friends at Little Caesars, where I decided to return to the food industry. I was hired as the Director then VP of Software Engineering. For three years, we implemented a brand-new POS system across numerous restaurants. Then, last year, the head of support retired and I chose to transition from development back into support—a field where I spent my first 15+ years in IT. Now, I’m back to what I love—solving problems.

The Pressing Issues in Customer Experience Today

I believe the most important aspect of applications is their intuitiveness. Many applications need to function in a similar way because there’s an educational gap when it comes to technology. The good news is that younger generations—those under 30 or even under 40—have grown up using iPhones and similar devices, so they are already familiar with modern technology. However, for those who are just now adopting these tools, we need to ensure that everything is more intuitive. While some applications are more user-friendly than others, the ultimate goal should be to create a seamless and consistent user experience.

Innovative Trends Transforming Customer Experience

AI and artificial intelligence are the big buzzwords right now. I’ve worked with AI and found it both enjoyable and valuable. Like any emerging technology, it’s the latest trend and the key is to adopt, adapt and continue growing with it. It’s easy to use, fun to explore, but also serves as a foundation—something not to be taken for granted.

Key Initiatives to Enhance Customer Experience

My philosophy is simple—if I make you interact with technology inside our restaurants, we haven’t done our job. It should just work—seamlessly and effortlessly. With that mindset, it becomes clear that if someone ever has to troubleshoot—reboot a system, unplug and reconnect a device or perform any manual fix—then something went wrong on our end. The employees in these locations are there to serve customers and ensure they get their food, not to struggle with technology issues. That’s the core principle we need to instill in everything we build: if a user has to touch it, we in technology didn’t do our job.

The Future of Customer Experience

I believe AI and generative AI will greatly enhance the customer experience as they continue to learn and improve over time. While people may sometimes try to override AI or say they do not need it, I see it as a valuable tool for challenging and expanding our mindset.

Advice for Senior Leaders and Upcoming Professionals

I would encourage people to use AI and interact with it. In a recent conversation, I advised someone to start by pulling the data, running a query and seeing the results first. Then, engage your own judgment—ask yourself if it’s 60 percent, 40 percent or maybe even 80 percent there. This approach allows you to assess it firsthand and develop a sense of trust. Building trust with new technology is essential, especially since it’s constantly evolving. You have to continuously engage with it to strengthen that trust.