Ed Dougherty

The scene is a packed meeting held by Orlando-based Massey Services at the 40-year-old family business’s Mid-Year Leadership Conference held annually in July. The gathering of managers from across a 10-state territory offers an opportunity to connect, recognize successes, coach, train and develop rising talent.

Ed Dougherty rises to inspire, speaking about the connection between one’s head and heart. He speaks with passion, confidence and conviction, filling the room with gusto you can grab onto — a contagious drive to learn, do and live the company’s core values as “not just words,” he said.

Then he jumps up on a chair.

“We are Massey! We are Massey!” the now retired executive vice president and chief operating officer (COO) chants, riling up the room of colleagues, who stand and join his fist-pumping cheer.

“Ed was a leader that created a huge sense of pride for all of our team members,” said Darlene Williams, regional vice president, Massey Services, describing Dougherty’s personable nature and motivating spirit. She’s known him since she joined the company in 1994.

Dougherty learned the business from the “bottom up” during his 33-year tenure at Massey Services. “You just get to work,” he said of a discipline he learned from his father at a young age; and later from the firm’s late founder Harvey Massey, who in 1992 hired Dougherty to open and run a new Tampa service center.

“You can’t manage what you don’t know, and you can’t ask people to do what you haven’t done,” said Dougherty, a consummate professional and teacher whose leadership style was never to micromanage, Williams said.

“If there was ever an issue I was working through, Ed’s first question to me always was, ‘How do you want to handle it?’” she said.

Dougherty said, “I led by example and gave people on our team the same experiences I had, encouraging their development by doing the right thing, being honest, instilling our values and culture — our mission statement is our heart and soul — and building trusting relationships.”

All this he learned by watching and doing, with Mr. Massey setting the tone and inviting every team member into the fold as family.

A ‘FOXHOLE’ GUY

In the early 1980s, Dougherty and his wife Dana, packed up their car with $50 to spare and a Gulf gasoline credit card to fuel a trip from Detroit to Atlanta. After rolling into town, Dougherty lined up a few job interviews and landed at ChemLawn (now TruGreen) in a telemarketing position, selling services to homeowners across the country.

“I grew an interest in the industry and felt like we were really helping people,” said Dougherty, who was promoted and transferred as the company’s growth accelerated. Eventually, ChemLawn was acquired by ServiceMaster.

A number of Dougherty’s early mentors, such as Barry Troutman, Adam Jones, Rick Beard and Ron Munson, had since joined Massey Services. “Why don’t you come over?” they suggested. This why-not segued into a more strategic plan when Mr. Massey called Dougherty and bought him a plane ticket to visit Orlando.

Dougherty wasn’t so sure. But Mr. Massey was convincing, and the trip involved visiting three of the company’s service centers in Florida as part of what was essentially a multi-day interview. This was Dougherty’s first exposure to the way Mr. Massey walked the talk. “I was impressed,” he recalled.

Mr. Massey asked: “If you were to move to Florida, where would you want to live?”

The Doughertys had moved around the country with their children, and Dana had family in Tampa. It seemed an obvious choice. “OK, I’m going to open a service center in Tampa,” Mr. Massey told him.

Dougherty was officially the service center’s first general manager after a few months of training at headquarters to learn the Massey Way.

“It was family-oriented and right away, they took me under their wing,” he said, noting he shared the same personal and professional values that stand today, believing strongly in Massey’s team-oriented culture where people make the difference, as well as their focus on staff development.

“We didn’t have an office manager or salesperson and there were two service technicians,” he said. “So, you just get right to work. I’ve been in an attic when it’s 100 degrees outside so I know what that feels like, and I’ve done every role in every job — no different than [President and CEO] Tony Massey and Mr. Massey, both of whom started out as termite technicians.”

Promoting from within grows strong leaders throughout the organization, including Dougherty. He rose through the ranks and championed similar pathways for others.

Dougherty grew the Tampa location, covering Naples, Fla., to Spring Hill, Fla. This accounts for about 20 service centers today. “This territory came from one little office,” he said.

He and Tony Massey were expanding their territories in tandem while forming a longtime partnership and friendship. Dougherty recalled a brotherly spirited competition to win a monthly plaque given to the fastest-growing service center. “Going into one December, I had six of the months from that year and Tony had five,” he said.

When Tony clinched the last month’s award, the two landed at a tie.

Two years after joining the company, Dougherty moved from Tampa to Orlando to become the general manager of the commercial business in Central Florida. “From there, I continued to take on additional responsibilities,” he said.

This included commercial division manager, regional manager of South Florida, Central Florida, Georgia and The Villages, and then vice president of Green-UP Landscape Services in 2009.

After a year, Dougherty’s career advanced to yet another rung on the ladder when he was promoted to executive vice president, consumer services. In 2011, he became executive vice president of operations and was named COO in 2016.

In his 33 years of working at Massey Services, Dougherty has never called in sick. “I may have showed up late or gone home early because I didn’t feel well, but I always showed up,” he said.

Dougherty has always been a hard worker, said Bill Dymond, chairman of Lowndes law firm, who sits on the Massey Services board of directors and worked closely with Dougherty at the nonprofit event management organization, Florida Citrus Sports.

“He leads by example, for sure, but also by building and encouraging others and helping them see the positive side of things and opportunities for success,” Dymond said, calling him a man of his word.

“The cliché ‘a foxhole guy’ comes to mind when I think of Ed,” Dymond said. “He will be there for you if you need him.”

HEAD AND HEART

The formula for success at Massey Services centers on its core values, established by Mr. Massey and lived out by team members, and a mission that is “our heartbeat,” Dougherty said.

At the top is total customer satisfaction — building long-term relationships with customers and team members “because we want them here for a lifetime,” Dougherty said. “Mr. Massey always said, ‘We have a blank checkbook to satisfy a customer.’”

Environmental responsibility emphasizes sustainable practices and stewardship, and growing a team-oriented culture requires ongoing training and communication. Community engagement is also a priority, along with delivering innovative services.

But below the surface of these values are lessons Dougherty and other Massey leaders have taken away from both its founder and Tony.

“‘Do what needs to be done when it ought to be done, whether you want to or not.’ That was Mr. Massey’s way of saying ‘Why put off tomorrow what you can do today?’” said Dougherty, who took those words to heart. He even had those words framed for each of his five children.

“He also taught me that effective managers are good teachers,” Dougherty added. “People have to understand the lesson, the mission and the purpose behind it. You have to be organized and that doesn’t mean a clean desk. It means understanding your priorities and working on what’s important today.”

Positive influence comes from motivating others personally and professionally. “How you go about this is critical,” Dougherty pointed out. “Your team has to believe you and follow you. That happens when you lead by example.”

Communication is key — and delivery equally so. “You’ve got to communicate with passion and purpose, verbally, non-verbally and in writing,” Dougherty said.

An open-book culture of transparency shows team members, “We have nothing to hide,” he added.

“Tony is no different in his values,” Dougherty said. “The apple didn’t fall far.”

A lesson he learned from Tony early on was the importance of coaching in the field and not allowing his office to become a water cooler. “When I reported to him as a general manager running a service center, he came in one day and saw a lot of team members hanging around my office. When everyone dispatched, he came in and said, ‘Let me teach you something. Your office is not a social club. It’s designed for two things: one, it’s your domain; and two, it’s where you bring people in if there’s some behavioral change that has to occur. They should know they’re being invited in to fix something.’”

He added, “But get out from behind your desk, get out and do your coaching and cheerleading away from your desk and in front of everyone — but not from inside your office.”

Tony Massey emphasized the great level of respect Dougherty’s team has for him as a leader. “He is up front and honest when there is an issue and helps talk through it with our team members,” he said.

Tony Massey added, “While Ed reported to me for most of our professional time together and we had a really strong working relationship, we also have an incredible friendship.”

The families are very close and the couples travel and celebrate milestones together. “Tony has always separated business from personal, and while we had some heated discussions, this was because he is such a good teacher,” Dougherty said. “Aside from my wife, Tony is my best friend. He has traveled this journey with me every step of the way and continues to do so.”

Dougherty has extended this direct yet amicable, family feel to colleagues. Williams joined Massey two years after Dougherty came on board, and the two formed a great friendship. Dougherty became her manager in 2008. “While it can sometimes be a difficult relationship shift, Ed made it easy because he is so personable,” she said.

Steve Castino sits on the Massey Services board of directors and is chief growth officer at the business advisory firm Rehmann, also working closely with Dougherty through Florida Citrus Sports. “Ed never seems to have a bad day and is so much fun to be around,” he said. “He lifts up others around him and treats everyone with so much kindness.”

This is the lead-by-example way Dougherty impressed on those he interacted with: the Massey Way.

“We talk about the three Cs in your journey at Massey Services — Confidence, Conviction and Commitment. You build your Confidence through your work and actions, and then you move on to a stage of Conviction,” he said. “Conviction is when you know you’re performing worthwhile work, that what you’re doing is beneficial. Then you get to a stage called Commitment. This is when your head and heart come together and it’s no longer Massey Services, it’s ‘our company.’ That’s when team members really take ownership, and we’ve got so many people who are on that journey.”

This is the head-and-heart message that resonates with longtime colleague Darlene Williams. She said, “It’s very motivating for new team members to hear.”

AN INCREDIBLE JOURNEY

“This business is not made up of one person and it was never meant to be that way,” Dougherty said of his decision to retire on March 31, 2025. “With that comes an opportunity for someone else or maybe several people.”

Dougherty reflected that there’s really no “right time,” but perhaps if there’s a right season, last spring was it.

“I’m healthy, I five children and eight grandchildren. My wife, Dana, has been the absolute rock of the family, and eight years ago, she retired from her career as a CPA and chief financial officer,” Dougherty said. “She made a lot of sacrifices, and I missed a lot of football, baseball, cheerleading and dance recitals. Now I have an opportunity to go to all of those and give my grandchildren my undivided attention.”

Dougherty added that if he had it to do all over again, “I’d do it the same way,” in regards to his time at Massey Services. “It’s just an incredible journey. The Massey family has been wonderful to me, my family, and our team members, and they treat everyone with nothing but respect and integrity. I’ve been very fortunate to work for a company like that. I love them all.”

Lately, Dougherty is spending more time golfing and traveling. He continues to serve on the Florida Citrus Sports board, of which he is a past president and chairman. “Ed is one of the most well-respected professionals in the Central Florida business community and his impact on Florida Citrus Sports has been tremendous,” Castino said of Dougherty’s involvement.

But retirement doesn’t mean an exit. After all, Massey Services’ mission is also the heart of who Dougherty is personally.

So, he has sold “a few accounts” since his retirement and enjoyed watching the business add its tenth state, Alabama, with an office in Huntsville. “Massey Services is a constant in my life,” he said.