Chief of Staff Spotlight: Tony Hickombottom

What is a Chief of Staff and what do they do? There are none better to ask than the Chiefs themselves. In this series, we talk with current and former Chiefs of Staff about their role as well as their personal motivations and secrets to performing it well.


  • Name: Tony Hickombottom

  • Location: Atlanta, GA

  • Current title: Business Consultant, Kids 'R' Kids International, Inc.

  • Former COS Role: Special Projects Manager, Jimmy John's Franchise, LLC (2013-2016)

  • Industries: Sports, Food & Beverage, Education



Tell us a little bit about how you found your former COS role as Special Projects Manager for Jimmy John’s.

I had just started my MBA program at the University of Illinois at Urbana-Champaign when one of my professors (who would become a mentor to me) asked me what I wanted to do with my degree. I was previously a sports agent and wasn’t entirely sure what I’d do next, but I’d always been interested in franchising. The professor mentioned that Jimmy John’s had its headquarters in Champaign, and encouraged me to reach out to Jimmy directly. Sort of on a whim, I wrote Jimmy a letter (on paper!) and just explained that I was in the MBA program and interested in learning more about his journey and the franchise industry. I didn’t really know what to expect, but a few days later I heard back from Jimmy, who responded to my questions. We started emailing back and forth, and the next thing I knew, I was spending the day with him at the headquarters. I ended up doing my internship after my first year with Wal-Mart, but I had kept in touch with Jimmy and after I graduated, he agreed to hire me with the caveat that I’d work harder than I’d ever worked before but that it had the potential to really pay off if I excelled. Following my internship with Wal-Mart, I had the opportunity to join them full time, but I was intrigued by Jimmy John’s and I knew I’d always wonder “what if” if I didn’t accept the position. I felt like it was a once-in-a-lifetime offer.

How did your education and professional background help you in this role?

I think the MBA was helpful, but Jimmy wasn’t handing me the job because of my degree. I think he liked the fact that I reached out and kept in touch with him, that I was persistent. I had to prove to him that I could work in his environment, and that I was reliable, had a good attitude, and was a hard worker. The longer I worked there and proved that I was a go-getter and would figure out how to get any job done, the more responsibility I was given to handle larger and even confidential projects.

My previous experience in sports was very relationship-oriented and very dependent on building trust. I learned how to talk to anyone in a way that was both professional and friendly. That helped at Jimmy John’s, where I was working with everyone from hourly store employees to the CEO and had to know how to best communicate with all of them.

What were your responsibilities in this position?

Anything that came across the desk of my boss, the President & CEO of Jimmy John’s, had the potential to come across my desk. When I came on board, they created the position for me, so it wasn’t clearly defined to start. The general idea was that I would be sort of a utility player who would work directly with the President & CEO and would be required to travel. (Very few details came with the offer.) I spent the first three months training in the stores and going through store manager training, which is required of everyone who works in the corporate office. The next 3 months was spent shadowing every department so that I understood what they did.  By the end of my first 6 months I had an understanding of what just about everyone in the office and in the stores did. I started working closely with/for my boss, traveling 3-5 days a week to deal with everything from real estate and construction to operations and marketing—basically, wherever they needed me. One week I might be attending a high-level meeting or working in a store to figure out a new market or program, and the next week I might be sitting at my desk analyzing spreadsheets all week.

As one example of how diverse the job could be, my boss asked me at one point to put a drive-through on a building at one of our locations. The building had been there for 20 years and had never had a drive-through, and of course, I had zero experience with anything like this. I spent the next 6 months meeting/talking with attorneys and architects and even attended city council meetings to get it done.

What was the most interesting part of your job?

Seeing the way the President & CEO ran one of the country’s fastest-growing restaurant chains with more than 2,500 locations. It’s much more complex than simply making sandwiches; the level of detail with which they run the company and seeing how they did it was incredible. My boss was knowledgeable about everything that went on in the organization and was very hands on.  I learned more about business during my time there than any school could have taught me.  I appreciated having the opportunity to have a front row seat to that kind of leadership as I hope to be in a position like that one day.

How long did it take you to feel comfortable with your boss and what helped you establish trust with him?

The first year was tough. It was an environment unlike any other I had been in. It is its own culture. It is far from Corporate America, but it is also not “do what you want, when you want.” They are maniacal with the details and there can be a lot of micro-managing at times. And when you throw in being in a role that is not clearly defined, and you don’t always know why you are doing something or where you are going, it got very frustrating, especially if you believe companies should fit in certain boxes. This company fits in its own and is proud of it. (But it works for them.) It was not until I changed my outlook and put trust in my boss that he wasn’t just stringing me along that things began to feel more comfortable. I realized the amazing position I was in to be able to learn from the President & CEO of one of the top brands in the country. I also started to see the knowledge gains I had made from situations that I once thought had no real purposes at the time. Around this same time, I noticed that my boss was entrusting me with more projects and more confidential information. I began to better understand my role and understand what he wanted from me and how he wanted those things. My mindset changed, things clicked and, all of a sudden, I was getting way more out of the position and enjoying it more. Additionally, my boss and I started to build a friendship as we traveled together more, and I truly felt like I was often filling the role of right-hand man.    


What are you doing now and how did the COS experience help you get to this point?

I’m now working as a business consultant for a franchise child care company. After I left Jimmy John’s, my wife and I moved to Atlanta on a whim. My broad experience at Jimmy John’s proved to make finding my next job somewhat challenging.  While many potential employers were impressed with my experience, it was difficult for them to categorize me as my skills didn’t neatly fit in one bucket. My pay had been commensurate with a Director or Vice President, but I didn’t have a decade of experience in one industry, as many positions were looking for. Additionally, my time at Jimmy John’s showed me that I prefer roles where I’m not pigeonholed, so I was looking for a specific type of position, which also added to the challenge. My current position as a business consultant sort of started like my role at Jimmy John’s in that Kids ‘R’ Kids had never had anyone in the position they were looking to fill and it was somewhat undefined. It’s a family-owned company that is really starting to grow, so my franchise experience is very helpful and the position has really developed into one that is a little bit of everything, from internal operations and developing teams and processes to planning and executing strategic initiatives. 

If you were to hire a COS, what qualities would you look for?

I’d look for a well-rounded individual who is willing to take on any challenge. Being a COS is not about being the smartest person in the room or having x amount of industry specific experience; it’s about being a quick and willing learner who can apply their previous experience to the current position. It is about the person who will roll up their sleeves and do whatever it takes to get the job done; someone who looks for solutions rather than excuses.