Episode 102: How to Build a 1,600+ Employee Company That Still Feels Personal

On this episode of Marketing Moves, we sat down with Jerry Schill, President & CEO of Schill Grounds Management, to talk about scaling a service business from a 10x20 storage unit to 37 locations across multiple states and Canada. Jerry shares what it takes to grow through acquisitions, transition into commercial maintenance, and build a people-first culture that can withstand rapid change. If you’re building a business and trying to grow without losing your culture, this one’s for you.

On this episode of Marketing Moves, we sat down with Jerry Schill, President and CEO of Schill Grounds Management, to talk about what it really takes to scale a service business without losing the culture that made it successful in the first place.

From operating out of a 10x20 storage unit in Avon to leading a 1,600+ employee organization across seven states and Canada, Jerry’s story is not just about growth. It’s about focus. It’s about retention. And it’s about building something that lasts.

Jerry didn’t set out to build a multi-state commercial landscaping powerhouse. Entrepreneurship started as a short-term opportunity between college graduation and a corporate job. But once he experienced the autonomy, creativity, and ownership of running a business, there was no going back.

In 1993, he and his brother went all in. The early days were filled with long hours, used equipment, and learning business fundamentals in real time. What separated them wasn’t resources. It was a mindset. They were curious, competitive, and smart enough to surround themselves with people who complemented their strengths. “We were smart enough to surround ourselves with people that complemented who we were and what we loved to do,” Jerry shared.

That self-awareness became a growth multiplier.

For nearly two decades, the business focused heavily on high-end residential construction. But after 2008, Jerry recognized the risk of relying solely on project-based revenue. The solution was a bold shift into commercial maintenance and recurring revenue.

In 2010, they made the move and committed fully. No half steps. No divided focus. Inspired by the “hedgehog concept” from Good to Great, they doubled down on the one thing they could scale long term: maintenance.

That decision created stability, predictability, and ultimately, expansion.

One of the biggest takeaways from our conversation was Jerry’s perspective on retention. Sales matter, but they are not the end game. In commercial services, contracts are multi-year, and relationships are layered. Losing a client can undo years of work.

“It could take years for us to get a client, and you can lose them really quickly if you don’t satisfy the promises that you made."

Schill’s growth has been fueled by consistency, proactive communication, and real relationships. Technology supports the experience, but it does not replace it. Account managers are present. Site audits are delivered in person. The focus is long-term trust.

Since 2020, Schill Grounds Management has completed 16 acquisitions and grown to 37 locations. With that kind of pace, culture can fracture quickly. For Jerry, protecting culture has been the hardest part of scaling.

He built the company by being hands-on and present. Growth forced him to evolve, to trust more, and to slow down when needed. “Just because you’re the owner or the visionary doesn’t mean that you’re above breaking the business."

That humility is what allows scale to happen without losing identity.

Today, the company operates under The Landscape Collective, a house-of-brands strategy that preserves local legacy while aligning around shared core values: be employee-centered, stay customer-focused, and champion the communities you serve.

Across every stage of growth, the playbook has stayed consistent: put the right people in the right seats, invest in technology that supports scale, and double down on culture.

Tools like HubSpot and Aspire power their tech stack, but Jerry is clear that technology is just that, a tool. “The technology should be used as a tool, not as a replacement for relationships.”

The real engine is people.

If you are building a service-based business, Jerry’s advice is straightforward: don’t quit. “You’re one failure away from getting it right."

Schill Grounds Management didn’t grow because of one breakthrough moment. It grew because of disciplined focus, long-term thinking, and an unwavering commitment to retention over quick wins.

Growth is exciting. But sustainable growth is intentional.