1851

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&nbsp;<a href="https://www.caringtransitionsfranchise.com/?utm_source=1851franchise.com&utm_medium=article&utm_campaign=caring-transitions-leslie-pennington-jacksonville-2729463" target="_blank" rel="nofollow">Caring Transitions&nbsp;</a>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.&nbsp;1851 spoke with Pennington to learn more about her story and her decision to join the&nbsp;<a href="https://1851franchise.com/caringtransitions/info">Caring Transitions</a> franchise family.&nbsp;1851 Franchise: Frame your personal story for us. What do you want us to know?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.1851: What did you do before franchising, and how did you decide franchising made sense for you?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.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?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.1851: What excites you most about this company?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.1851: What do you hope to achieve with your business? What are your plans for growth?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.1851: Is there anything else about your story you want us to know?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.1851: What advice do you have for other people thinking about becoming franchise owners?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.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 350 locations, Caring Transitions’ compassionate, experienced professionals minimize stress and relieve the burdens of life’s transitions. To learn more visit&nbsp;<a href="https://www.caringtransitions.com/?utm_source=1851franchise.com&utm_medium=article&utm_campaign=caring-transitions-leslie-pennington-jacksonville-2729463" target="_blank" rel="nofollow">https://www.caringtransitions.com/</a>.

Franchisee spotlight graphic with photo of Leslie Pennington and Caring Transitions logo

Caring Transitions Franchisee Feature: Leslie Pennington in Jacksonville, Florida

1851 Franchise

After a 20-year corporate marketing career, Pennington is turning her attention to community impact—helping families navigate life’s toughest transitions with dignity, empathy and practical support.

From Campaigns to Compassion: Leslie Pennington Launches Purpose-Driven Caring Transitions Franchise in Jacksonville, Florida

caring-transitions-leslie-pennington-jacksonville

Caring Transitions

Why Consider a Corporate Career Change? Find Meaningful Work Helping Others With Caring Transitions

why-consider-a-corporate-career-change-find-meaningful-work-helping-others-with-caring-transitions

Comfort Keepers

How This Financial Strategist Built a Flourishing Purpose-Driven Business With Comfort Keepers®

how-this-financial-strategist-built-a-flourishing-purpose-driven-business-with-comfort-keepers

Fitness Premier

Fitness Premier: A Legacy of Excellence, Built on a Foundation of Fitness

fitness-premier-a-legacy-of-excellence-built-on-a-foundation-of-fitness

Busy Bee Jumpers

From Solo Hustle to Franchise Muscle: Why Converting to a Busy Bee Franchise Just Makes Sense

busy-bee-jumpers-franchise-conversion-opportunity

Paris Baguette

Paris Baguette Franchise - Anusha Jonnala and Swapna Varala - 1851 Franchise

Blending Tech, Hospitality and Health Care: How Three Women From Different Worlds Came Together to Build a Paris Baguette Franchise

paris-baguette-franchise-flower-mound-texas

Buying a Franchise Masterclass

 Franchise Opportunities

Get Support Buying a Franchise

How to Buy a Franchise White Paper

How to Buy a Franchise

How to Sell Franchises

How to Grow a Franchise

Find a Franchise Supplier

1851 Franchise Opportunities

Franchisor News

Franchisor Power Rankings

FranCamp Mastermind Summit

Franchise Development Website Builder

Franchise Resources

What ALEC-Laffer's Report Means for Franchising

Website Awards

Power Rankings

About 1851

Advertise on 1851

Contact 1851 Editorial

Terms of Use

1851 Login

GROWTH CLUB LOGIN

facebook

instagram

twitter

linkedin

youtube

Dickey's Franchisee Backlash - Lawsuits - Disputes - 1851 Franchise

Texas-Based Dickey’s Barbecue Pit Grapples with Franchisee Backlash

dickeys-barbecue-pit-franchisee-lawsuits

Design with person in blazer, with laptop, holding sign that reads "LOOKING FOR A JOB"

Uptick in Jobless Claims Points to Continued Instability in Labor Market

jobless-claims-franchise-growth

Extraordinary Brands Acquires CycleBar and Rumble, Shaking Up Boutique Fitness Franchising

extraordinary-brands-cyclebar-rumble-boxing-acquisition

NJCAR v. Ford - New Jersey Supreme Court Limits Standing Under Franchise Practices Act

New Jersey Supreme Court Limits Standing Under Franchise Practices Act

new-jersey-franchise-practices-act-njcar-v-ford

Planet Fitness Franchisees Donate $100K to Support Texas Flood Relief - 1851 Franchise

Planet Fitness Franchisees Donate $100K To Support Texas Flood Relief

planet-fitness-texas-flood-relief

Hely and Hiral Patel Bring Their Longtime Dream to Life With The Brass Tap

brass-tap-franchise-pasadena-maryland-hely-hiral-patel

Navy Veteran and Professional Artist Couple Open Caring Transitions in Texas

Navy Veteran and Professional Artist Couple Set Out to Build a Purpose-Driven Business With Caring Transitions in Texas

navy-veteran-and-professional-artist-couple-set-out-to-build-a-purpose-driven-business-with-caring-transitions-in-texas

Why This Real Estate Broker Decided To Bring Caring Transitions to Central Texas

caring-transitions-san-marcos-kyle-chad-hardin

graphic image of a franchisee spotligh aman kaur of voodoo brewing

How This Trio of Friends Is Brewing Up Community With Voodoo Brewing Co. in Prosper, Texas

voodoo-brewing-franchisee-aman-kaur-prosper-texas

Hooters Leans Into Franchising With Closure of 30 Company-Owned Stores - Agg - 1851 Franchise

Hooters Leans Into Franchising With Closure of 30 Company-Owned Stores

hooters-franchise-model-company-owned-closures

1851 Keyword - The Secret To Succeeding With a Part-Time Franchise Is Picking the Right Model

The Secret To Succeeding With a Part-Time Franchise Is Picking the Right Model

part-time-franchises-picking-the-right-model

"Come in, We're OPEN" sign against abstract background

Small Business Optimism Dips, Raising Concerns for Franchise Owners

small-business-optimism-dips-raising-concerns-for-franchise-owners

Wendy's CEO Kirk Tanner Steps Down - Breaking News - 1851 Franchise

From Campaigns to Compassion: Leslie Pennington Launches Purpose-Driven Caring Transitions Franchise in Jacksonville, Florida

MORE STORIES LIKE THIS