CEO Lisa DeSisto Listens to her Heart and Head
Lisa DeSisto, who relishes organizing parties and events, devised an elaborate scavenger hunt for her son’s birthday celebration. There was just one catch: one of the boys forgot to close the gate of the alpaca pen. In short order, 11 alpaca and 11 boys were running around “in full-out pandemonium.”
“But they were pretty easy to herd—both the kids and the alpaca,” she says. “With candy and grain, it all worked out.”
Lisa is clearly a woman who knows how to get things done. And that’s good, because her job as chief executive of Masthead Maine is a challenging one.
Masthead Maine owns a network of newspapers, websites, and magazines that reaches 78 percent of Mainers. Under its umbrella is the Portland Press Herald/Maine Sunday Telegram, which together with four other daily newspapers and more than two dozen weekly publications makes it the largest media group in the state. As CEO, Lisa is responsible for about 500 employees.
Her role, as she’s described it, is to build a productive, healthy company culture while maintaining financial discipline. How she has done it—with both a quick wit and firm focus on what matters—is a case study in both leadership and work-life balance.
Commitment to journalism
Managing the bottom line of a news organization that’s still weighted toward print is tough. With the advent of the web in the 1990s, advertisers slowly began shifting dollars away from traditional media, like print and TV, to digital. That trend culminated last year when, for the first time, U.S. digital ad spending surpassed that of traditional media, according to eMarketer, a research company specializing in digital marketing.
Newspaper publishers have struggled to offset the loss of advertising revenue by boosting reader subscriptions, niche editorial products, and events, while cutting costs—like newsroom jobs.
But Lisa opted for a different route: to save on printing and distribution. In March, Masthead Maine switched the Monday editions of its four daily newspapers to digital-only. The strategy was to preserve quality journalism by preserving jobs. And for that she has earned the loyalty of staff and respect of the community.
“She’s focused on providing quality journalism to the people,” says Nancy Marshall, a Maine public relations expert, who has been connecting people and the press for almost 40 years.
Good journalism takes money because the process is hard. “It requires attentive listening to diverse sources, dogged examination of data and other records, and close observation of government at work. It takes time and skill and requires on-site support of editors and other news leaders who live in the community and care about it,” explains Joyce Dehli, co-chair of the Pulitzer Prize Board, in the journal Nieman Reports.
Lisa’s commitment to deeply reported local journalism is apparent to anyone thumbing—or scrolling—through the Portland Press Herald. This year, for example, Eric Russell investigated the state’s mishandling of a case of suspected medical child abuse. Penelope Overton revealed how Maine’s slow marijuana rollout has cost millions of tax dollars and thousands of jobs. And Gillian Graham uncovered an alarming rise in domestic violence during the coronavirus crisis. All three reporters are staff writers on the payroll of the newspaper.
As Lisa ticks off news events like the pandemic, the presidential election, and Black Lives Matter, she says, “More than ever, I feel that people, especially in Maine, appreciate the value of local journalism and the importance of understanding what’s happening around them.”
They have rewarded top newspapers with a surge in subscriptions. Digital subscriptions at the Press Herald have doubled over the past year and have pushed overall monthly circulation up over the prior year since July of 2019.
“Yes, our monthly paid readership is growing,” Lisa confirms.
Subscribers have discovered some other “nice-to-have” benefits, too. There are the Daily Headlines email, commenting privileges, monthly PERKS giveaways, event access, and special subscriber-only offers. “But the local exclusive journalism is the primary reason people subscribe,” Lisa emphasizes.
Among the events created by the Press Herald is “Like a Boss,” a live Q&A in which Lisa talks one-on-one with leaders from Maine employers, including L.L. Bean, Northern Light Health, and Hannaford Supermarkets. Despite the pandemic, the program continues in a virtual version. In addition to delivering sponsorship revenue, it contributes mightily to a sense of community, which Lisa embraces as part of the Masthead Maine corporate mission.
It’s also a nourishing personal experience for a “life-long learner,” as Lisa calls herself. For example, she points to a valuable insight from Colby College President David Greene, who espouses “Begin with Yes.”
It can become frustrating when people crush ideas because they failed in the past, Lisa says. “Things happen so quickly in our world” that she encourages revisiting them with a positive attitude. In meetings, she has been known to say, “We’ve got to President Greene this . . .”, meaning “Begin with Yes.”
Yet, as innovative as she is, Lisa maintains critical perspective on how much energy to invest in initiatives like events. They are time-consuming to organize but yield only a small slice of overall revenue, she says. Firmly focused on return on investment, she doesn’t get distracted just because something is new or exciting.
“She ‘gets’ what a sustainable business model means,” says Reade Brower, Lisa’s own boss. He is the entrepreneur and champion of local journalism who owns both Masthead Maine and MaineStay Media, formerly Courier Publications (the parent company of this magazine). In 2012, Reade began a now-legendary media buying pattern which has saved struggling smaller outlets by centralizing common functions, like printing.
While growing digital subscriber revenue, Lisa also appreciates loyal print customers, so she is thinking carefully about the transition to digital publishing.
Digital is how she made her mark at the Boston Globe, which she joined in 1995 two days after Boston.com launched. Her success at growing the online news and entertainment site vaulted her from marketing manager to chief advertising officer and general manager of Boston.com in 17 years.
The digital hub of Boston.com scored a place in Globe history as “a major source of advertising revenue,” according to Dana Hatic, who profiled the newspaper from its founding in 1872 on.
In 2012, Lisa moved to Maine for a new challenge. She was recruited by Donald Sussman, a hedge fund financier who bought the Press Herald and a group of papers known as MaineToday Media. With Lisa at the helm, he “invested millions setting them on a more sustainable path following years of mismanagement,” says the Columbia Journalism Review.
Then, in 2015, he sold MaineToday Media to Reade Brower. “When I was asked by the former owner to take over the stewardship of the flagship Portland Press Herald and Sunday Telegram, he told me his recent hire of Lisa was one of the biggest assets he was turning over. The full impact didn’t hit me until I watched the kind and deliberate way she managed us through the abyss. She is smart, leads by example, and with her heart and her head.”
Humor also pervades her leadership style. “One of my proudest accomplishments, even though it wasn’t my parents’ favorite, is that I was voted Class Clown at my high school,” Lisa says.
She grew up in Stoneham, Massachusetts, ten miles outside of Boston. In sixth grade, she joined the color guard and drill team, which not only marched in local parades but competed nationally.
“I still love parades,” she says, adding that every time she hears Vicki Sue Robinson’s “Turn the Beat Around” or the Turtles’ “Happy Together,” memories of those “really fun, but fiercely competitive” times come back.
This experience taught Lisa the importance of teamwork. Later in high school, the gym teacher, who had admired her active participation in class, recruited her as manager of the men’s varsity basketball team. She traveled with the team, made announcements, and kept stat records, learning that all the little things have a big impact on the game.
It was her first experience with management. Today, as she talks about “life-changing journalism,” she regularly cites the mission-critical employees who are “making collection calls for outstanding advertising balances or helping a customer who didn’t get the paper that day.”
While a teacher encouraged her to study economics at the University of Massachusetts at Amherst, Lisa’s mother knew her best and suggested communications. “Because you’re so good with people,” she wrote in a letter Lisa still has today.
Later, as a new mom herself, Lisa turned to her mother again. Some mornings it felt hard to just get a shower, let alone read the Globe cover-to-cover—which was the expectation. So, as she commuted in unpredictable traffic, her mother read the paper to her on the phone. (Mrs. DeSisto also peppered in her own commentary.)
Women in senior leadership roles
Women still contribute to Lisa’s success, and she is the first to recognize it. Without prompting, she lists the “really strong women” in senior positions on both the editorial and business sides of Masthead Maine. After a recent company quarterly meeting on Zoom, one employee commented how refreshing it was to see so many smart, capable women leading the company.
Some, with resumes featuring the Boston Globe and Hearst Communications, Lisa has recruited. Others, with powerful Maine connections and knowledge, are the long-term veterans she has succeeded in retaining. This balance shows a lot about her leadership and values.
Working in Maine brought some big personal changes, too. Did she have to slow herself down? “Driving I certainly did,” she says. Now she no longer suffers in the paralyzing, unpredictable Boston traffic which devoured “22 to 90 minutes” of her time in each direction.
She also left behind an “always-on” culture. “You always had to have your phone on you, and you were always responding to emails,” she says. “One of the things I noticed about Maine right away is that there is this delineation between your work life and your personal life. You want to respect people’s family time.”
Millennials in particular care about work-life balance. That fact bodes well as Lisa seeks to attract and retain the next generation of leaders.
“We have several women (some with five years of experience or even fewer) who blow me away with their talents—understanding analytics, mastering online tools, and having exceptional emotional intelligence,” she says. “I’m inspired by them and know our newspapers have bright futures if we can keep them engaged.”
Maine has given Lisa a life she loves, with pleasures well known to people who have grown up “the way life should be.”
Her Instagram tells the story. It is full of photos of dogs, tomatoes ripening on the windowsill, a Tuxedo cat, thumbprint cookies, and family fishing trips. Her sense of humor pops up once again in a picture of a well-gnawed Croc beside a Pudelpointer with a “who me?” expression.
“It’s not lost on me for a second how fortunate we are just to have this space,” says Lisa, who is now 57. She lives on a 24-acre farm in North Yarmouth with her husband, Tim Padgett, and her 14-year-old son, Andrew. It is also home to goats, chickens, and those 11 alpacas.
And, yes, here is a CEO with personal knowledge of alpaca poop (“we call it Alpaca Gold”) and its benefits as a fertilizer (“a very robust garden”). Last summer she and her son planted potatoes, an intriguing crop. “When you’re picking potatoes, it’s like a treasure hunt, right?”
Mother and son also play pickleball and golf together. Lisa relaxes by tackling jigsaw puzzles, a pastime Andrew has now outgrown. “That’s one of the things that’s heartbreaking to me,” she admits, sharing a sentiment well known to mothers.
It is no surprise that Lisa’s management philosophy is to support the “whole person” because she seems to value the many dimensions of her own life now in The Pine Tree State.
“It was really life-changing to get to be here in Maine,” she says. “Otherwise, I’d probably be stuck in traffic right now.”