Caring Transitions Franchisee Feature: Leslie Pennington in Jacksonville, Florida

Leslie Pennington spent two decades leading national campaigns and driving growth for some of the country’s top financial and insurance brands. But deep down, she always knew she was meant to do something more personal, more impactful. Now, as the owner of Caring Transitions of West Jacksonville, Pennington is channeling her strategic mindset and heart for service into a mission-driven business. Focused on helping families through downsizing, relocation and estate sales, her franchise is built to meet a rising community need — with compassion at its core.

Leslie Pennington: Launching a Caring Transitions franchise is deeply personal for me. It’s not just a business — it’s a calling. I’m passionate about making a meaningful impact in the community by helping families navigate life transitions with compassion, dignity and practical support. This is the start of a new chapter for me where purpose meets entrepreneurship.

Pennington: Before franchising, I spent over 20 years in marketing and strategic partnerships, leading national campaigns and managing high-impact initiatives in the financial and insurance sectors. I’ve always been entrepreneurial at heart, but I knew I wanted to start something with an existing support system and proven framework. Franchising offered the right blend of independence and infrastructure to allow me to scale with confidence and focus on impact from day one.

Pennington: Before becoming a franchisee, I saw franchising as a more structured and less risky path to entrepreneurship — which was appealing to me because I’m naturally risk-averse. I liked the idea of following a proven system rather than starting completely from scratch.

Now that I’m in it, I’ve realized that while structure is a huge asset, success still depends on choosing the right franchise — one that aligns with your values, your strengths and the kind of impact you want to have. Not all franchises are created equal, so it’s important to take your time and find the right fit. When you do, it can be incredibly empowering.

1851: What made you pick this brand?

Pennington: Caring Transitions offered the structure and support I was looking for, but what really set it apart was the mission. I wanted a business where I could be hands-on, make a difference in people’s lives, and still have a solid operational framework behind me.

As someone who values having a clear roadmap, I appreciated the systems in place — from training to technology. But even more importantly, the brand's focus on compassion, service and community felt like a perfect fit. I wasn’t just buying into a business — I was joining a purpose-driven network that reflects who I am.

Pennington: I’m excited by the heart behind the brand. Every service we offer — from downsizing and estate sales to senior relocation — is rooted in empathy and making people’s lives easier during difficult times. It’s rare to find a business model that allows you to be profitable and purposeful at the same time, and that’s what excites me most.

Pennington: My short-term goal is to become the go-to resource for senior transition services in West Jacksonville, earning trust one family at a time. Long term, I plan to grow through strategic partnerships and potentially expand into a second territory. I want to build a scalable business that creates jobs, supports families and becomes a pillar in the community.

Pennington: This franchise is more than a career shift — it represents a lifestyle change. I’ve made a conscious decision to step away from the corporate grind and build something that reflects who I am and what I stand for. I also want to be a role model for my son by showing him what it means to lead with purpose and take bold steps toward your dreams.

Leslie Pennington: Take the leap, but do your homework. Make sure the brand aligns with your personal mission, not just your financial goals. Franchising isn’t a shortcut — it’s a framework. Your success depends on how much you invest in learning, adapting and serving your community. And most importantly, trust yourself — you’re more capable than you think.

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 350 locations, Caring Transitions’ compassionate, experienced professionals minimize stress and relieve the burdens of life’s transitions.