“I started as a teenage kid that loved to work outdoors. I called and asked the coolest, nicest landscaping company in our area if I could have a job,” he said.
“…I didn’t even have my license yet. That’s how young I was. The owner’s question to me was, ‘Well, how would you get to work? How would you get to our shop?’ I was like, ‘I’ll bike.’”
And he did. For two years, Zimmerman pedaled his way to Tassey Landscaping in Hollidaysburg, Pennsylvania, rain or shine, until he finally got his driver’s license.
“And that’s how I got started,” he said.
That bold teenager grew up and eventually founded SynkedUP, a software company that’s transforming how hardscaping businesses operate. But his story isn’t just about building a successful tech company, it’s about a career journey that every aspiring hardscaper can learn from and the “owner’s mindset” that changed everything.
Laying the Foundation for a Career
Starting as a crew member for Tassey Landscaping, Zimmerman quickly found his niche in water features that demanded both technical skill and artistic vision. He loved the challenge and the creative freedom it offered.
“You can check whether you’re doing it right on a hardscape with a level and a tape measure, but with a water feature you can’t really. It’s more of an eye situation. It’s like an artist and a paintbrush. Does it look good? Does it not look good?” he said.
He worked as a foreman and a crew leader for Tassey installing high-end design-build projects. If there was a water feature involved, it was assigned to Zimmerman’s crew.
He then set his sights on Aquascape’s Artist of the Year award.
“I still remember, watching that award being given out to some of my friends and peers in the industry and I remember being like, I am gunning for that. I am going for that. I want that award,” Zimmerman said.
It took four to five years of relentless focus, but he achieved it. He took home the title in 2017.
“I really dedicated myself to learning the craft of water feature building and making it look natural and doing them well,” he said.
Pivoting From Employee to Owner Mindset
As his skills continued to grow, so did his hunger for growing his career.
Facing the reality of seasonal work in Pennsylvania and wanting to buy a home after getting married, he approached his boss about making more money. The conversation didn’t go as planned.
Then a mentor shared advice that became Zimmerman’s North Star: “Don’t just ask for more money. Ask your boss how you can make the company more money so that you can make more money.”
This piece of wisdom triggered what Zimmerman calls flipping “from an employee mindset to an owner mindset, even though I was still an employee.”
“The light bulb went on for me. It makes so much sense. It’s what got me into doing more for the company,” he said.
In addition to installing projects nine months a year, Zimmerman took on marketing responsibilities for Tassey.
“Through the season I was installing projects and through the winter I was full-time doing marketing, website, content, creation, all of that,” he said. “I started making YouTube a regular thing for us. I was doing daily social media content and building a following. I put in a lot of hours, but I genuinely enjoyed that. I was essentially holding two roles in the same company to give me a full-time, year-round position in a seasonal landscaping company.”
The Problem That Sparked a Solution
As Zimmerman became more involved in the company, he found a seat at the leadership table and started to offer ideas for business processes and process optimization. With his experience in the field and in the office, he brought a unique perspective.
“We ended up in this world of having multiple software products to just manage our project lifecycle. It felt like we were using multiple products to do really just one thing,” he said.
The inefficiency was maddening—data scattered across different systems, gaps partially filled with spreadsheets, and no single source for project information. Not to mention the frustrations from crew leaders in the field, something Zimmerman was all too familiar with.
“I was literally just a crew lead, working out field working on the as the end user of these systems and processes. I have a lot of empathy for that person out there in the field. It’s raining. Their hands are covered in mud and they need to figure out something they need to understand. They need to find out some information about the job or they need to log information. I have a lot of empathy for those real-life boots on the ground,” he said. “…If it doesn’t work for the end user, if the end user doesn’t buy in and it doesn’t solve a problem for them, then the whole thing is at risk.”
At the time, Zimmerman’s father was working in the tech industry on a software program and Zimmerman felt like the stars aligned. His father helped connect him to contacts in software development and he started creating what would eventually become SynkedUP.
“We need to build something to get this all into under one roof,” he said. “That’s where we came up with the name SynkedUP. We wanted to get our process synced up.”
What started as an internal solution for Tassey Landscaping evolved into something much bigger. Through his network of contractors built at industry conferences, Zimmerman realized, “This problem is not unique to us. I developed a vision of solving this problem not only for our company, but for the industry at large.”
His goals extend beyond just software. It’s about creating alignment where “both the team members, employees and the owners and leadership are optimizing and working for the same thing.”
It’s an expansion on the mantra he learned from his mentor when he shifted his own mindset. When everyone understands and works toward the same goals, both profitability and individual growth become achievable.
Advice for Aspiring Hardscapers
When hiring for his own company, Zimmerman looks beyond technical skills.
“What I’m really fishing for is things like: Are you a problem solver? Do you name problems. Or do you solve problems?” he said.
He seeks people who invest in their own growth, who view challenges as opportunities rather than obstacles, and who possess the emotional intelligence to collaborate effectively.
“You have to be willing to do the small things before you can do the big things. Nothing can be below you,” he said. “Make yourself so valuable that the company can’t help but promote you.”
He also wants aspiring hardscapers and early career hardscaping employees to experience that same mindset shift he had years ago.
“Flip from an employee mindset to an owner mindset. Supporting the owners and leaders in the companies you work for in achieving their business goals will inherently help you grow your own career,” he said.
Sharing His Knowledge and Experience
At the 2025 Hardscape North America, Zimmerman will be sharing the systematic approach that separates profitable businesses from struggling ones. Drawing from his experience both in the field and helping hundreds of contractors through SynkedUP, he’ll expose the common tripping points that hold businesses back and provide clear, actionable solutions.
“Trying harder is not a strategy,” Zimmerman said. “Everybody has a goal of being profitable. What’s the difference between the ones that actually are profitable and the ones that aren’t? The ones that are profitable have a system. It’s not an accident; it’s an outcome of the actions you’ve taken.”
His session promises to turn “the vague into clarity” and provide attendees—whether owners or early career employees—with the specific metrics and systems that create sustainable success. Because as he learned long ago, when you help others get what they want, you can get what you want too.
From biking to landscaping jobs as a teenager to building a company that serves hardscaping contractors nationwide, Zimmerman’s journey proves that with the right mindset, there’s no limit to the paths you can take and how far you can go in the hardscaping industry.
