Stepping up: Next-generation leaders take the helm at four Maine family businesses

Once every generation and sometimes in between, new leaders step up to run family-owned enterprises — which in some cases also means an ownership transfer. To find out what those transitions are like for those involved, Mainebiz checked in with four Maine businesses with next-generation executives at the helm.

Mother-daughter blanket business

A favorite family blanket inspired Beth LaSala to start a blanket business called ChappyWrap in 2006 now led by her daughter, Christina Livada, who took the helm as president last year.

Livada, 34, runs the business from her home in Cape Elizabeth, which is also home to the blanket that she and her brother used to fight over as kids. Soft and decorated with little sheep and lambs, “Lamby” provided comfort when one of them was home sick from school.

“It was everybody’s favorite blanket for years,” says Livada, who grew up in the Boston area. “We didn’t know at the time what made it so special. We just knew it was the best blanket.”

LaSala, 65, has equally fond memories of what her family called the “sick blanket.” Years later, she and her sisters searched for a similar blanket at stores nationwide but never found anything that matched its feel, washability, durability and quality.

After researching the market and manufacturing process, LaSala decided to create her own, made from a high-quality, natural cotton-blend and high-performance fiber. She teamed up with a business partner to start ChappyWrap, working with a manufacturer in Germany.

The brand, launched in Massachusetts, is a nod to Chappaquiddick Island on Martha’s Vineyard. Initial growth came from sales at shows and other in-person events that Livada helped out at on weekends during college.

She left her speech-pathology job in July 2018 to join her mom at ChappyWrap as vice president of sales and marketing after LaSala’s business partner retired.

“When I first came on board, it was just my mom and I running the company, and we both wore a lot of hats,” says Livada, who now oversees a remote team of eight employees.

Livada describes her current role as “keeping the wheels moving on a daily basis and working with the rest of the team to make sure they have what they need to be doing their jobs.” The team includes her husband, Drake, as sales and marketing director, while her mom moves towards retirement.

Early on, mother and daughter rebranded the business with a new website, new logo, new designs and sizes and new packaging as they shifted towards an ecommerce-driven business model complemented by social media.

“It was right at the time when Instagram and influencers were taking off — that whole world I didn’t know anything about,” LaSala says. Grateful to her daughter for bringing new life into the business, she says: “The energy level at 30 is a lot different than it is at 60.”  Today, the customer base is mostly women ages 30 to 55.

Working with factories in Germany and Poland, the company makes blankets, throws and shawls from a blend of 58% premium cotton fibers, 35% acrylic and 7% polyester. Today, direct-to-consumer online sales account for 85% of business with the rest from wholesale.

Thinking back to when she started working with her mom, Livada says they were very conscious about putting boundaries on talking business outside of work.

“You know that lines are going to be blurred,” she says, “but you don’t really know how much they’re going to be blurred until you’re in them.” They’ve had to be just as deliberate about keeping personal stuff separate from work.

“There are times when we will not agree on something in the business, and we have to be like, ‘OK, now we’re not mother-daughter, let’s talk about this from a business perspective.’”

That was also hard at first for LaSala, who says, “If either one of us would push back, it felt a little bit personal in the beginning. We recognized that going forward to this day.”

Livada’s long-term goal for ChappyWrap: “To provide comfort to as many homes and families as possible through our blankets.”

The accidental insurance executive

When Marney Chalmers left her hometown of Bridgton for New York City to study at the Parsons School of Design, she never envisioned a career in insurance.

“I don’t have a background in insurance, other than the fact that my last name is Chalmers, and I wanted nothing to do with the family business growing up,” the 40-year-old says.

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Photo / Courtesy of NAHGA

Marney Chalmers

That all changed a few years ago, when she returned to Bridgton to take a job as vice president of sales and marketing at the National Accident Health General Agency, or NAHGA, a third-party administrator specializing in secondary accident insurance. The company, founded by her father, Bill Chalmers, in 1991, processes claims for 11 of the premier underwriters of health and accident insurance for colleges and universities, sports leagues, day care centers and others.

“Nationally, there’s only a couple of companies that do what we do, which is incredibly niche and specialized,” Marney Chalmers says of NAHGA.

She joined the firm in 2016 after a decade at West Elm, a Brooklyn, N.Y.-based division of Williams-Sonoma Inc. that sells furniture and home décor. She loved that job, where she was a sourcing manager and spent a lot of time on international travel.

One day, she got a call from her father asking if she had any interest in returning to Maine and to work for NAHGA. While her first reaction was “No way,” she was eventually persuaded.

The reason she accepted: “I was at a pivotal point in my life,” she recalls. “I knew I wanted to have a family someday, and I knew I needed to focus on me and my family and on my relationship with my father, who had a lot of health issues.”

Initially overseeing sales and marketing, Chalmers succeeded her father as president and CEO in January 2022. Her father, 72, also passed the torch to the next generation at Chalmers Insurance Group, also based in Bridgton, but still serves as chairman of that company.

At National Accident Health General Agency, Marney Chalmers leads 50 employees and says she has no regrets about making the move.

“We have definitely grown since I’ve joined, and I’m proud of it,” she says. “I’m excited to see where the company is going.”

Asked what she’s learned from her father along the way, she says: “He’s a man of his word and integrity is everything for him.”

One example of that is when an employee asked for financial help to pay a heating bill, and her father went out and personally filled the employee’s fuel tank.

“We’re a family-owned business, and we treat everybody like family,” she says.

Her sister, Dottie Chalmers Cutter, is an owner and vice president of operations at Chalmers Insurance Group.

Happy to have her sister who’s also her best friend back in Maine, Dottie says. “We’ve always been each other’s cheerleaders — and I didn’t realize how much I was missing my cheerleader, until she moved back to Maine.”

From mowing lawns to running Cross Insurance

From mowing lawns for Cross Insurance when he was a teenager to running the company as president and CEO, Jonathan Cross has spent his whole career at one firm.

But the 46-year-old insists he had to prove himself like any other employee at the Bangor-based insurer, which has grown from a one-man, home-based operation started by his grandfather in 1954. Today, Cross Insurance is one of the largest independent insurance providers in the Northeast, with 1,105 employees on the payroll, including more than 400 in Maine.

“It wasn’t a given that I would automatically get a job at the family business,” says Cross, who succeeded his father as president in 2020 and as CEO in September. “I had to apply and take whatever work was available.”

That meant stints in different departments during his studies at Husson University, then becoming a full-time account manager after graduating with a degree in business administration.

“I wanted to move into sales, but I had to work my way into that as well,” he recalls. “That was the same expectation of my cousin, who is younger than me and came up the same way.”

His father, 71-year-old Royce Cross, is now the company’s chairman. Reflecting on his son’s early days at Cross, he mentions the time that Jonathan spent a day working in the basement — and later emerging to find an empty building.

“It was a snowy day, so we closed the office and sent everybody home, and we forgot he was in the basement,” Royce Cross says. “We laugh about that a lot.”

On a more serious note, he says that passing the baton — and the leadership titles — to his son was a natural evolution.

Royce Cross’s only regret: “We probably should have done it earlier.”

The company, which has made more than 120 acquisitions, today has offices in Maine, New Hampshire, Vermont, Rhode Island, Massachusetts, Connecticut, New York and Florida. Even after more than 50 years at the company, Royce Cross has no plans to retire anytime soon and meets with his son for regular, early-morning check–ins.

Asked what lessons from his father he’s taken on board, Jonathan Cross says: “His ability to remain calm and thoughtful in very complex situations … I saw that in my grandfather and my uncle as well. I try to remember that in more challenging times.”

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Photo / Left: Jim Neuger; RIght: Courtesy of Cross Insurance

Royce Cross, left, is now chairman of Cross Insurance, while his son Jonathan is president and CEO. The two hold early-morning check-ins.

From sweeper to flooring-company president

Like Jonathan Cross of Cross Insurance, Joe Capozza III of Capozza Floor Covering Center got started in his family’s business doing menial tasks.

“I swept the warehouse when I was a little kid and then spent my high school and college vacation time working in the warehouse and in the field with our installers,” Capozza says.

The company’s roots go back to 1974, when his grandparents founded Capozza Tile Co. out of their basement furnished with a borrowed desk, a manual typewriter and an adding machine — and the family station wagon as the only company car.

After graduating from Bryant University in Rhode Island with a bachelor’s degree in business administration, he worked as a sales representative for Bentley Mills, a California-based commercial carpet manufacturer, in Maine, New Hampshire and Vermont, getting a front-row seat to the operations of a large international business, before returning to Maine in 2009 to join Capozza Floor Covering Center as a commercial project assistant.

“Working for an international company helped me see how things run in the corporate world, which I then brought to the family business,” he says. “That gives a different perspective.”

He held various roles over the years, working his way up to commercial division manager by 2013. A year later, he became vice president of Capozza Tile Co., which at the time encompassed the company’s commercial and residential divisions as well as Old Port Specialty Tile Co., a store in Portland. In 2016, he oversaw the acquisition of an industrial flooring business called TMT Floors, which has since rebranded as Capozza Concrete + Epoxy Flooring.

In February, Joseph F. Capozza passed the ownership baton to his three children. The siblings lead the company as a team, with Joseph Capozza III as president and his sisters as vice presidents. Katie Capozza also runs the Old Port Specialty Tile Co., a store in Portland, while Tia Green manages the company’s residential division.

“It’s been good so far,” Capozza says of the setup. “It’s really a team effort, and we’re very conscious and appreciative of that.” Echoing that sentiment, Green says: “I trust my brother and sister, which makes it easy for us to work together.”

While their father is no longer an owner, he remains involved as a mentor and in other ways.

“If someone needs a hand,” the son says, “he’s willing to help out wherever he can.”

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Photo / Tim Greenway

From left, siblings Tia Green and Katie Capozza, both vice presidents at Capozza Floor Covering Center, and Joe Capozza III, president of the third-generation Portland company that owns Old Port Specialty Tile Co.