Can This Woman Bring Tourists Back to Boston?

After the pandemic tanked tourism in this town, Martha Sheridan is now leading a multimillion-dollar effort to lure visitors everywhere from Nubian Square to the Freedom Trail. Is she revolutionary enough to get the job done?

Photo by Christopher Churchill

Martha Sheridan had been in her dream job as the CEO of the Greater Boston Convention and Visitors Bureau for exactly one year when she made a trip down to Kissimmee, Florida for a conference. It was February 2020, and just about the only discernable difference from every other business trip she’d ever taken was the unexpected overabundance of hand sanitizer. When an expert in the Chinese tourism market gave a presentation citing the newfound coronavirus’s impact on outbound travel, Sheridan wondered what might happen if Chinese visitors couldn’t make it to March’s Seafood Expo at the Boston Convention and Exhibition Center. The notion that her entire industry could instantly disappear never entered her mind.

Then it did. The first week of March, Sheridan was back at work when her vice president of destination services reached out over the phone with some devastating news. With her staff at her office near Copley Square (one of the most popular landmarks in the city that Sheridan was charged with luring visitors to) she learned that the problem wasn’t the lack of Chinese executives coming to the Seafood Expo. Instead, the event, which regularly draws 22,000 visitors to Boston and fuels restaurants’ and hotels’ bottom lines, had just been postponed, and would eventually be cancelled altogether.

From there, wave after wave of bad news crashed down upon her. Sony pulled out of the Pax East gaming convention. Race officials canceled the Boston Marathon. Commencements disappeared. Soon, even Sheridan—a blonde with an easy, throaty laugh and an irrepressible personality who thrives on human interaction—was forced to retreat. She packed up her South End condo and set out along an eerily empty I-95 south to her summer home in Saunderstown, Rhode Island.

What happened next was unexpected. Yes, business travel dried up like a stale croissant, and tourism all but vanished for a while, yet remarkably, Sheridan found ways to score several wins. Between taking socially distanced walks and baking sourdough bread, she persuaded the legislature to give her a Brink’s truck full of funding. The following year she helped launch a revolutionary re-brand for the city, and this year helped land a major global sporting event for Boston.

None of this is to say that Sheridan—or Boston—is out of the woods. Due to some of the nation’s tightest COVID restrictions and the region’s long, cold winters that limit venues’ ability to hold outdoor events, Boston’s tourism industry has suffered more than many other cities. “We’ve been at the back of the pack for the recovery,” says Sebastian Colella, vice president at the Pinnacle Advisory Group, a locally based hotel industry consultancy. Business travelers who historically made up a third of Boston visitors, Colella says, are still largely stuck in Zoom rooms. Hotel occupancy during commencement season was down and hoteliers are having trouble hiring enough staff.

What Sheridan has in her favor, though, is an unusual skill set that has already proven to be effective in these highly unusual times. If you want to know what that skill set is, don’t look at her résumé detailing her impressive career helming major organizations, overseeing multimillion-dollar budgets, and working magic in Providence as the CEO of that city’s convention and visitors’ bureau. Sheridan’s success stems from a job not even worthy of appearing on her LinkedIn page: tour guide.

Sheridan once worked at the lowest rung of her industry, as her sister Tricia Evangelista describes it, “getting up at 3 a.m. to drive to New Bedford to get on a bus to go sing songs with senior citizens.” It was a job where a sense of humor, a gift for the gab, the ability to project confidence, and on-the-fly problem-solving skills were the last line of defense to ensure the hard-won vacations of legions of tourists a year did not go off the rails. “You had to troubleshoot everything,” Sheridan recalls.

In some ways, not much has changed. Sheridan is facing a steep climb to get heads in beds, butts in restaurants, and elevate Boston to the top tier of destination cities alongside New York City, Las Vegas, San Francisco, Orlando, and Chicago. With the high-risk stakes and fortunes of so many Bostonians hanging in the balance, the future is now in the hands of a hard-charging, out-of-state executive channeling her inner tour guide—which may be precisely what Boston’s tourism industry needs.

Photo by Ken Richardson

This spring, I found myself standing underneath a large plastic tent at the Flynn Cruiseport Terminal during a grip-and-grin event where Boston’s tourism officialdom gathered in business attire to mark the kickoff of the 2022 cruise season. Sheridan strode in wearing a black dress, a gray jacket, and pumps with her long hair loose over her shoulders, and started shaking hands and making polite morning chitchat, projecting the air of a fearless leader and someone who means business.

That was before Sheridan spied an old friend from across the room. Out of nowhere, she let out a peal of glee—sounding more like a giddy vacationer than a representative of the business elite—and rushed in for a bear hug. And in that instant, I could suddenly see the other Sheridan, the fun, fearless, and imminently likable extrovert laughing it up.

Forty years ago, that friend, David Crooks, was her boss at a New Bedford–based company called Paragon Tours and Travel, which hired her to lead motorcoach tours to Atlantic City, New Orleans, and Quebec, sometimes traveling for weeks at a time. It was her first job out of college and where chatting up strangers became, in a sense, her vocation. “You met really interesting people all the time,” she said of the tour guide life. Reminiscing with Crooks, Sheridan recalled how rule number one of the job was that you couldn’t sit in your designated seat. Instead, you had to stand in the aisle and keep your balance as the bus zoomed down the highway—regardless of the potholes on the road or unexpected short stops. She acknowledges that her equilibrium, confidence, and fearlessness served her well as she guided a flock of disoriented tourists who depended on her. At once, she could make them feel confident that they would safely get to their destination and have a blast along the way.

Those lessons have served Sheridan well in business meetings such as the one at the Cruiseport, surrounded by lots of men who, at least physically, tower over her. “I’m 5’1”, so when I walk into a room, it’s really hard for me to gain attention immediately,” Sheridan says. “If I’m at a trade show with one of my male colleagues, they’ll introduce me, ‘This is Martha from the Boston CVB.’ And someone will have to lean down to shake my hand, and they’ll say, ‘And what do you do at the bureau? Are you in sales?’ And I’m like, ‘No, I’m actually the CEO.’ And it’s always like, ‘WHAT?’”

The trick, she says, is to maintain a poker face and overwhelm the doubters with competence and a don’t-mess-with-me persona. Dan Donahue, president of the Saunders Hotel Group and the chair of the visitors’ bureau board, remembers an early conversation with Sheridan when he commented on the running of the bureau, and she snapped, “Stay out of my operations”—setting a tone for their relationship and earning his respect. “She’s funny, she likes to laugh, she’s generous of heart, she’s thoughtful,” Donahue says, and “sometimes when things are tough, she can be a little bit of a pusher.”

Martha Sheridan is one part tour guide, one part bold business executive. / Courtesy photo

The first thing Sheridan pushed for when she came to Boston was an understanding among the powers that be in tourism and government that Boston needed to change the way it promoted itself. No easy task. After all, in his nearly three decades as tourism CEO, Sheridan’s predecessor, Pat Moscaritolo—East Boston native, former MassPort executive, known quantity in a who-you-know field—had overseen an impressive expansion that brought throngs of visitors to the Back Bay, downtown, and the now-bustling Seaport, giving Boston some of the best hotel occupancy rates in the country. It seemed like times were good.

From Sheridan’s standpoint, though, Boston wasn’t competing the way it should or could. Travelers were coming from China, the United Kingdom, and Germany, but the rest of Europe was mainly going elsewhere, as were luxury travelers from Japan and the Middle East. Major sporting events were not giving the Hub a chance. “The old adage from Boston was: ‘People are filling our hotel rooms…and I can’t get a room for my aunt for under $500. Why do we need to promote?’” Sheridan says.

The answer, she argued, was that Boston wasn’t able to contend on a national playing field. Her promotional budget was $7.5 million in 2019–2020, compared to $24.7 million in Washington, DC and $35.2 million in Atlanta. Attracting meetings and drawing visitors is a zero-sum game, and Boston was losing conventions, events, and leisure travelers to cities with larger promotional budgets that could entice meeting organizers with perks and discounts.

Many of those cities had something Boston did not: a self-funding mechanism called a “tourism destination marketing district,” which allows hotels to assess a fee on a customer’s final bill and send the proceeds to a dedicated tourism promotion fund. In Massachusetts, hotel occupancy taxes primarily flowed into the general fund, so tourism leaders were at the legislature’s mercy, begging for tuppence year after year.

For years, regional tourism officials lobbied for the idea on Beacon Hill, but Moscaritolo and the Boston tourism industry never got behind it. Having Sheridan suddenly on board was now a game-changer. She hired John Lambeth and his firm Civitas, a travel industry consultancy that helps states form these marketing districts, and got busy promoting the concept. Then came the pandemic, which in some ways made the argument easier. “It gave the leadership in Massachusetts a whole new appreciation for the tourism industry,” Sheridan says, “because you don’t know what you’ve got until it’s gone.” Ultimately, the measure, which permits Massachusetts’ 17 regional tourism councils to create marketing districts, was tacked onto an economic development bill that passed into law in January 2021.

A final hurdle was forming Boston’s actual district. Sheridan needed signatures from 62 percent of the hotels in the sector that had 50 or more rooms. To get them fast, Sheridan says, “we set a strategy,” by which she means—in tourism-industry fashion—she held a party at the Fairmont Copley Plaza. “Wine and cheese,” she says with a laugh. “It is the hospitality industry, after all.”

On a June 2021 afternoon, in a blissful lull between COVID variants, hotel managers in dark suits signed the necessary paperwork in one wood-paneled room and raised a toast in another. As the afternoon sun shone through floor-to-ceiling windows, Sheridan and her executive vice president, Hilina Ajakaiye, and senior vice president of sales Beth Stehley offered thanks. “Rarely in the same year do you see the legislation passed and the district formed,” says Lambeth, who has gone through the process in cities across the U.S. Donahue recognized the qualities in Sheridan that made it happen fast: forcefulness mixed with the ability to bring people together. “She’s a cheerleader by nature,” he says. “That was the tour guide in her, that brought people together when they had to be.”

Hotels started collecting the fee in October 2021. Sheridan predicts that, as occupancy rates rise, the district will collect $22 million in 2022 and as much as $40 million in 2023. When I ask her how she’ll spend all of that cash, ideas tumble out of her. She wants to draw visitors during the cold, dark months of December, January, and February by subsidizing restaurant weeks and lodging discounts. She wants to hire new staffers to promote Boston to European, Japanese, and Middle Eastern luxury travelers who are currently choosing other destinations. She wants to work with Logan Airport officials to secure more direct international flights to Boston. She wants to go after big, high-profile events such as an NFL draft.

Still, Sheridan wasn’t only interested in expanding the number of people coming to Boston. Her most ambitious goal of all just might be expanding the places they go once they get here.

“She’s a cheerleader by nature,” Dan Donahue says. “That was the tour guide in her, that brought people together when they had to be.”

Like any good tour guide, Sheridan knows that people love attractions that are off the beaten track and beyond the touristy schlock. It makes them feel as though they’ve had an authentic, insider experience. At the Cruiseport event that day, there were signs that the city’s tourism arm was about to offer that more regularly. Two new promotional posters featuring people who, frankly, didn’t look much like the people under the tent were propped up near the podium. One of them featured Porsha Olayiwola, Boston’s poet laureate, a Black woman with beaded braids and a prominent nose ring, smiling and laughing.

When it was Sheridan’s turn to address the crowd, she alluded to the posters obliquely. “We love our traditional attractions here in Boston,” she said, name-checking duck tours, chowder, and the Freedom Trail. But “there’s so much more our city has to offer. All of our different cultures…all of our different ethnicities.”

For the Greater Boston Convention and Visitors Bureau, though, this represented a sea change in how it did business. For as long as anyone could remember, Boston didn’t have a clear message or story of who it is. Instead, outsiders were getting their impressions of Boston from Saturday Night Live, Sunday Night Football, Dennis Lehane books, and Matt and Ben movies. Boston had been reduced to marathon runners, lobster rolls, loudmouth Patriots fans, Whitey Bulger, and not much else.

Meanwhile, insiders say, the bureau was focused on serving its membership, which was largely made up of hotels, restaurants, and tour operators in the Back Bay and downtown. When Sheridan arrived, the bureau was spending the vast majority of its resources drawing meetings to the convention center and funneling visitors to the usual locations. She declared from the start that she wanted that to change. “We don’t want anyone to think that we are dismissing the old and traditional Boston,” she says. “We just want people to know that there are many, many dimensions to this city.”

Sheridan’s pivot immediately impressed then-City Councilor Lydia Edwards. “It would have been very easy for her to just focus on downtown and the glitz and glamour of the predominantly upper-middle-class neighborhoods,” Edwards says. Instead, “what I heard was someone completely compassionate about making sure Boston shined its brightest light and shined it in all colors and all languages and all neighborhoods.” Being an outsider was likely helpful. “She didn’t have any historical baggage with people or things or places,” says Donahue, the bureau’s chairperson. “She dove in, saw this need, and found a way with her team to fix it.”

Sheridan dispatched her staff to make promotional videos of Eastie, Roxbury, and Dorchester, featuring local businesses and street art. Her goal was to represent the city’s actual population: more than 50 percent non-white, with 29 percent of residents being immigrant-born and 140 languages spoken, though seldom portrayed in the script of a Mark Wahlberg movie.

Then came the pandemic, the murder of George Floyd, and an unexpected opportunity. The CARES Act, a federal coronavirus relief bill that passed Congress in March 2020, included $2 million to promote tourism in Boston. By April 2021, the contract for the “All Inclusive” Campaign went to Colette Phillips, a veteran public relations executive, and her creative partner, Proverb, a South End firm founded by Daren Bascome. Sheridan (with the Greater Boston Convention and Visitors Bureau) rounded out the trio of collaborators. Both Phillips and Bascome are Black Bostonians who had moved to Boston for college—Phillips from Antigua and Bascome from Bermuda. Sheridan was the most recent Boston implant of the three but, by definition, represented the city’s existing tourism power structure.

That Sheridan was committed to telling a different story, Bascome says, made it easy for the creative team to dive into a new approach of selling the city. “Oftentimes, strategy isn’t just what you say ‘yes’ to; it’s also what you say ‘no’ to,” he tells me. “And the obvious thing would have been to double down on tri-corner hats and baked beans and lobster rolls.”

Instead, the group grounded their initiative in data, engaging Heart + Mind Strategies, the firm whose research helped Las Vegas rebrand to fit changing consumer interests. They conducted focus groups and surveys of Bostonians as well as travelers who were Black, Hispanic, and Asian. “We were watching it in real time at night in our homes during the pandemic,” Sheridan recalls, and the results were, if not surprising, deeply sobering. Non-Black Boston residents called the city  “fun,” “smart,” “welcoming,” and “friendly.” Black residents found it “white,” “rude,” “unwelcoming,” and “arrogant.” To travelers unfamiliar with Boston, the city was “tough,” “traditional,” and “arrogant.” Bascome says it was clear that the impressions weren’t just based on rumors or TV shows. “Not only [did] they have a strong opinion, they almost always felt like they knew someone who had had a direct experience,” he says.

Those negative impressions could have serious economic consequences. In 2019, Phillips notes, Black Americans spent $63 billion on travel. “You have to ask yourself, how much of that $63 billion is Boston leaving on the table if they’re not targeting that market?” she says.

Sheridan viewed the data with a tour guide’s optimism and saw the results as just another challenge to hurdle. “We take the glass half full side,” she says, “which is to say, we have a lot to work with here as far as how we can shift the narrative.” The result was the city’s “All Inclusive Boston” campaign.

The goal was to play on well-known tourism terms and explicitly pitch to broader demographics. Part of the campaign was the “My Boston Accent” ad that started with an image of a young Korean woman riding a skateboard at Cambridge’s Lynch Family Skatepark, saying to the camera in Korean, “This is my Boston accent.” Celebrated anti-racist Ibram X. Kendi stood in the Boston Public Library and whispered the same line in English. Brian Moy, star chef of Shōjō in Chinatown, said the phrase as he held a sizzling pan. One vestigial white guy with a ginger beard said the line while raising a pint in a bar, but if you blinked, you’d miss him.

In its first months, the campaign played out in cities within driving distance to Boston: ads atop New York taxicabs and TV spots during basketball games in Philadelphia and New Jersey. Meanwhile, Sheridan’s office, using a service that tracks cellphone data, gathered anecdotal evidence that the messaging might be working: Some visitors to a convention wound up in Nubian Square.

Word is also spreading across the country and the world. Bascome watched Sheridan present the campaign to an international travel conference in Washington, DC, where she received a standing ovation. “The room was electric,” he says. “People were really impressed but also intrigued by the approach.” After all, he notes, Sheridan’s approach isn’t just promoting tourism—it’s trying to change the city’s story.

Sheridan is working to change the way people outside Boston see the city through initiatives like this ad campaign. / Courtesy photo

When I met Sheridan in her office this spring, she had a confession to make. That morning, after she went out for coffee, she did some low-grade stalking. She spotted two women who worked at Wayfair, trailed behind them, and eavesdropped on their conversation. Wayfair’s employees, who work at the company’s corporate headquarters in the same building as Sheridan’s office, had recently returned to working in person. “They were having this really strategic business conversation the whole way back from Starbucks,” Sheridan says. “And I thought, ‘That would never have happened if these two young women were working from home.’ It just doesn’t happen!” She pounded the table for emphasis.

Sheridan is on a mission to promote the glories of face-to-face contact everywhere. She is the leader of a national organization called “Meetings Mean Business” which, among other things, is lobbying for tax incentives to promote business travel. Closer to home, in her own office just a few weeks earlier, staff started returning to work three days a week. “It’s magic, I have to tell you,” she says of mandatory in-person Wednesdays. But her desire to promote face-to-face business meetings isn’t just because Sheridan is a consummate extrovert, a forever tour guide who feeds on human contact. Her success in Boston depends on it. While leisure tourism is exceeding pre-pandemic levels and conventions are returning in force, business travelers, who traditionally make up a full third of Boston’s visitor base, have not yet returned—and it is unclear if they ever will.

That isn’t the only challenge Sheridan faces. Amy Finsilver and Trish Berry, the general managers, respectively, of Fifteen Beacon and the YOTEL Boston, told me that during commencement season there were rooms still available, while in the past they would have sold out these dates years in advance. Foley also notes that many hotels’ biggest challenge right now is hiring, which, depending on who you ask, is either a result of a labor shortage or the industry’s failure to pay workers enough.

While Sheridan still has her work cut out for her, she continues to chase victories—and bring people together for face-to-face gatherings along the way. On the afternoon of June 16th, Sheridan, the members of her bureau, and other Boston power-brokers assembled together in a room at the Park Plaza. That day at 5 p.m., FIFA would announce which cities in North America would host the 2026 World Cup, one of the largest events on the planet. The bureau, along with the Kraft group, had thrown Boston into a pool of applications from dozens of cities across the country, Canada, and Mexico that were vying for one of 16 coveted host city slots. No one knew how the evening would unfold. FIFA had been tight-lipped about the winners, declaring, in no uncertain terms, that information would not be leaked. Sheridan, though, couldn’t let the possibility of a win go by without a celebration—and there was no way she was going to watch this one from a Zoom room with coworkers.

For Sheridan, the stakes were high that afternoon. If Boston won, the region would be on the hook for a ton of upfront costs, including providing efficient transportation from downtown to Foxboro, installing new turf on Gillette field, and changing signage along the roads and at the stadium to transform it into a typical-looking FIFA venue. On the plus side, the event would draw some 450,000 visitors and provide a $500 million economic boost. As Sheridan calculated her odds, she knew Boston had two new factors in its favor. She and her staff suspected that the new funding from the promotional district would help make the case that Boston had the money to pay for necessary improvements and changes. FIFA also required a document stating how the potential host cities addressed human rights. Sheridan hoped the “All Inclusive Boston” campaign would bolster the city’s case that it was committed to hosting all people from everywhere.

The room, buzzing with excitement, turned silent when the broadcast began. FIFA officials announced western cities first, followed by central cities, and at long last, after an agonizing wait, the winning cities in the East. Sheridan was positioned at a table near the screen. “Hard decisions. Are you ready for the final cities?” Ana Jurka of Telemundo asked FIFA President Gianni Infantino.

“Born ready,” he replied.

The first winner he announced was Toronto.

“We knew that. We knew that,” Sheridan shouted over the televised banter. It was unclear if she was trying to assuage the anxieties of the others in the room or her own.

“The second one,” Infantino went on. “Boston.”

“Boston!” Jurka said, before cracking a little joke. “Like, Bennifer might make an appearance.” But if you were there at the Park Plaza, you could barely hear her over Sheridan’s joyous whoops. She leaped up from her chair, arms in the air like a pro ball player, and handed out double high-fives louder and giddier than anyone else in the room.