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How Squeegee Squad Grew to 80 Locations Fast
An interview with Courtney Lightfoot at Squeegee Squad

Welcome to this week’s edition of The Workbench, a resource-rich weekly newsletter and podcast for home services entrepreneurs.
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This week, I had the pleasure of speaking with Courtney Lightfoot, CEO of Squeegee Squad, a window cleaning franchise system boasting over 80 locations. Courtney has been with Squeegee Squad for 17 years, helping the company grow from a single office with the founders to a national leader offering both residential and high-rise commercial services.
She shared the systems behind their franchise success, how she navigated the journey from employee to CEO, her honest view on using AI in home services, and what really separates top-performing franchisees from the rest.
The 7 Key Takeaways
Below are the most essential insights from my conversation that you can apply to your home services business today.
1. Finding the Right Franchise Fit
Courtney emphasizes that sales ability and a collaborative mindset are two essentials she sees in successful franchisees. Even if someone doesn't start with sales experience, being eager to learn and connect pays dividends—and leaning into the broader franchise network has fueled the biggest wins.
“What we're finding is with any small business, whether you're going it on your own or you're a part of a franchise system, experience in sales is going to be a huge impact on your business. That's not something you have to maybe come in with experience, but maybe you're open to learning more about it—you’re not afraid to get out there and introduce yourself. And the other component is those that do reach out to us, do have frequent communication. We find that those that really get involved in the franchise system, thrive because they're bouncing ideas, sharing wins, and learning from others in the network.”
2. Why Franchising Worked for Squeegee Squad
Not every business should franchise, but for Squeegee Squad, franchising was the ideal growth engine. Courtney explains that their model was highly repeatable and allowed the owners to teach others directly—creating more reach without being tied down to every location themselves.
“For us, franchising was a model we felt confident we could reproduce easily. We didn’t have to be in the day-to-day of every corporate unit. We could take what we knew, teach others to be successful in their market, and partner with them. Franchising made more sense than trying to own and operate every location directly, especially in a service-based business with the right systems.”
3. From Part-Time Admin to CEO
Courtney’s career journey started with answering the phones as a new mom, working part-time in the Squeegee Squad office. Over years, she took on new responsibilities and gradually became deeply involved in every part of the business. Being able to grow with the company gave her unique insights when stepping into the CEO role.
“I started just doing admin roles, part-time, really just helping out where I could. As the business grew, my role changed—from admin to tech support, training, even legal and accounting. For a long time, it was just the founders and me providing support for our franchisees. That’s where I learned every aspect of the company, which prepared me to step in as CEO.”
4. Navigating the Leap to Leadership
Becoming CEO is a leap—even for someone who knows the business intimately. Courtney openly shares she’s still learning, and that building real relationships with franchisees and support staff is crucial. Proactively seeking learning from other leaders, reading, and accepting feedback has shaped her leadership.
“Full transparency, I’m still navigating. The founders and the ownership structure really molded me along the way, so I had a solid knowledge base. But there’s so much to learn about managing people, setting meetings, keeping a pulse on every part of the company. I leaned into reading, listening to other leaders, and meeting with other franchise CEOs to gain new perspectives.”
5. Systematizing Support for 80 Locations
Managing 80 franchisees means facing constant new challenges, but Courtney points to Squeegee Squad’s continual investment in onboarding, training, and business coaching as key to helping franchisees ramp up faster and feel supported at scale.
“What helped us is building out the support structure, especially in the past couple of years. We doubled our support staff, added business coaching, and improved onboarding and training. Since then, franchisees have grown their businesses faster and feel better supported. Having that infrastructure means we’re there for them, even as we scale.”
6. AI in Home Services: Excitement and Caution
AI is the talk of the industry, but Courtney explains that for Squeegee Squad, it’s a blend of opportunity and caution. They’ve used AI for internal systems and templating, but put safety and compliance above all else—especially with the risks in high-rise commercial work.
“We started asking, how can we use AI to streamline our processes or make things more efficient—especially for developing templates and documentation for franchisees. Some franchisees use it on their sites. But we are cautious with safety components; OSHA and industry standards are critical in our work. We want to make sure we remain in control and ensure everyone stays safe. There’s future potential, but we’re moving carefully.”
7. Keys to Franchisee Success (and Struggles)
The brand alone won’t drive franchisee success. Courtney stresses that those who want to work the system, reach out for help, and don’t try to reinvent the wheel within the franchise are the ones who outperform. Those who take the playbook and run solo, without support, struggle more often.
“We see less success with franchisees who take the name and the brand, which is definitely recognized, but then try to reinvent the wheel or go off on their own. It’s the ones who follow the system, stay in touch, and use the resources who thrive most.”
Looking Ahead
Taking the CEO seat has been both humbling and energizing for Courtney. Her approach? Keep learning, stay team-oriented, and never assume you have all the answers—always trust in those around you.
“Consistently staying educated and remaining humble—you’re not going to have all the answers. Lean into your team, ask what they know, and listen. It’s all about bringing the team’s resources and perspectives together to move the system forward.”
Wow! You made it to the end; thanks for sticking with us.
The full interview is available on YouTube below, Spotify here, and Apple Podcasts here.