After Decades in Corporate America, Bobby Wilkinson Finds a More Meaningful Way to Serve Through Caring Transitions

After more than 25 years working in operations, marketing, and diversity and inclusion at some of the country’s most trusted companies — including State Farm, USAA and Charles Schwab — Bobby Wilkinson knew his next chapter needed to be different. He wanted more than just another job; he wanted purpose, ownership and the chance to serve others in a more personal way. That search led him to Caring Transitions. Launching his business in San Antonio Central on July 14, Wilkinson is combining his professional background and core value of empathy to help families navigate some of life’s most challenging transitions. 

1851 spoke with Wilkinson to learn more about his background, his path to Caring Transitions and his plans for the future. 

1851 Franchise: Frame your personal story for us. What do you want us to know?

Bobby Wilkinson: I spent over 25 years in corporate America in all kinds of roles — operations, marketing, diversity and inclusion — with brands like State Farm, USAA, TIAA and Charles Schwab. These companies are all focused on service — how to take care of your clients and customers in the best way possible.

After the last election, my role was eliminated, and I thought, “Maybe this next chapter of life is an opportunity to work for myself.” That’s what really kicked off this whole process — the desire to finally be in control of my future.

1851: What was your perception of franchising prior to becoming a franchisee, and what do you want people to know about franchising now that you are in it?

Wilkinson: I considered all kinds of business ideas, but one thing that drew me to franchising — especially a more established franchise — was the backend support. There’s an operating model that’s been refined over time, and success stories you can learn from.

That’s the advantage: there’s a blueprint for success that someone new, like me, can come in and follow. My experience with State Farm actually informed that idea — that structure and support can really make all the difference.

1851: What made you pick this brand? What excites you most about this company?

Wilkinson: I initially thought about getting into health care, but when I found Caring Transitions, I was drawn to how it sits adjacent to that space — it’s still about care, just in a different form. The whole idea of empathy — of helping people — really aligned with my values.

I talked to a lot of franchise owners and heard their stories — how this brand allowed them to own their future, make an impact and build something meaningful. That resonated with me. One owner in San Antonio invited me to see his team in action. Watching how passionate they were, how much they cared for their customers, how they even helped people recoup money through auctions or by clearing homes to be sold — it just clicked.

1851: What do you hope to achieve with your business? What are your plans for growth?

Wilkinson: Right now, I want to learn as much as I can. My goal is to build a great team, deliver a strong service and really understand the territory. If we do those things well — if we focus on building relationships and providing real value — I believe the business will grow naturally from there.

1851: Is there anything else about your story you want us to know?

Wilkinson: One of my first calls came from a local city council official. They had a constituent who needed help moving — someone who couldn’t afford it. I saw it as a great opportunity to help someone in the community and also learn the ropes.

Three Caring Transitions owners in San Antonio teamed up and got the job done — packed, moved and unpacked. The appreciation from this gentleman reminded me why I chose this path. It felt good to do something meaningful right from the start.

Something I learned during training is that success comes down to having a strong team that believes in the mission. If you find the right people who share the same values and care about the clients, everything else will fall into place. That’s been my focus these past few weeks — building that team.

1851: What advice do you have for other people thinking about becoming franchise owners?

Wilkinson: Really understand the financial investment. I thought I had a good handle on it, but once I started digging in and getting everything lined up, I realized it takes more than you think.

Whatever number you have in mind, add 25%. That’s not a regret — I’m still glad I did this — but it’s the advice I would give anyone: go in with your eyes open and be prepared. If you do that, this can be something truly amazing.

To learn more about franchising with Caring Transitions, visit https://1851franchise.com/caringtransitions/info.

ABOUT CARING TRANSITIONS:

Caring Transitions provides older adults and their families with the most trusted, respected and comprehensive downsizing, right-sizing, estate sales and online auctions, and move management solutions in the industry. Founded in 2006, the brand is committed to helping people in a compassionate and caring manner during life's many transitions while providing a total and easy solution for clients in their time of need. Through their proprietary online sales platform, CTBIDS, Caring Transitions also prepares clients for the process of liquidating assets through their own online estate sales auction site. With more than 400 locations, Caring Transitions’ compassionate, experienced professionals minimize stress and relieve the burdens of life’s transitions. To learn more visit https://www.caringtransitions.com/