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Mike Sheehan makes his mark at Hill Holliday

After succeeding the legendary Jack Connors at Hill Holliday, Mike Sheehan faced a question: Could he put his own stamp on the agency? He did.

Mike Sheehan has led Hill Holliday through technological changes and the worst recession in 70 years.Josh Reynolds for the Boston globe

Mike Sheehan drinks Dunkin' Donuts coffee, black. He eats at Chili's every other week. He has a life insurance policy from John Hancock, home and auto policies from Liberty Mutual, and multiple ­accounts at Bank of America.

For Sheehan, chief executive of the Boston advertising firm Hill Holliday, these are not just consumer choices. They are clients.

"You cannot be good in this business," he said, "unless you experience your clients on a daily basis.''

Sheehan's obsession with client loyalty — come to work with Starbucks, and you're fired! — helped him achieve what many considered a near-impossible feat: putting his own stamp on the agency after succeeding its legendary cofounder and chief executive Jack Connors. In the decade since Connors handed over the reins, Sheehan has led the agency through technological changes and the worst recession in 70 years — and managed to build an even stronger firm in the process.

When he steps down as chief executive on Monday, he will leave Hill Holliday, the nation's 14th largest ad agency, on a path toward its best financial year yet, following four years of record revenues and profits.


"My instinct was that Mike would do better than I'd ever dreamed of doing," Connors said. "And 10 years later, he has. I can look back and say he made me look good and made me proud."

Sheehan, who believes CEOs should be term-limited to 10 years, began planning his departure in early 2007 when he named his longtime colleague Karen Kaplan as Hill Holliday's president. In 2010, he told the agency's parent, the Interpublic Group of Cos. of New York, that she would be his successor and his last day at Hill Holliday would be his 10-year anniversary as chief executive.

On Tuesday, Sheehan, 52, of Norwell, begins a two-year stint as chairman, cutting back to just a few days a week in the agency's downtown Boston ­office and preparing for his ultimate exit.


"Karen has earned the right to be CEO of Hill Holliday, and she'll be great," he said. "And I've earned the right to do something else."

Sheehan, a writer at heart, grew up in Weymouth, where he covered local sports for the Weymouth News as a teenager. He worked in The Boston Globe library while attending St. Anselm College in Manchester, N.H., and after graduating in 1982, became a reporter for The Patriot Ledger of Quincy.

He stumbled into advertising when a small firm on the South Shore asked Sheehan's father if his writer son wanted to give the business a go. He did, and found he liked agency life, where, he said, you are paid to be optimistic.

He grew up on the creative side of the business at firms such as Clarke Goward in Boston and Leo Burnett in Chicago. He joined Hill Holliday in 1994 as a group creative director, tackling accounts such as Lotus Notes and Fidelity Investments and later pitching and winning Dunkin' Donuts as a client.

A year after his Dunkin' success, Sheehan left Hill Holliday for DDB Chicago to become executive creative director and run the McDonald's account, penning the "We Love to See You Smile" campaign for the fast-food giant.

Fred Bertino, president and creative director at rival Boston agency MMB, said Sheehan is among the rare people in the industry who combine creative sensibilities with business acumen.


"What makes people great creatively is what sometimes makes it impossible to be CEO or manager of any kind," said Bertino, who worked with Sheehan in the mid-1990s at Hill Holliday. "But Mike is one of those guys who can do great creative work, but also understand the broader business landscape."

On the Saturday after Thanksgiving in 1999, Sheehan, back in Boston to visit family and friends, took a walk on Castle Island with Connors. Connors, who had recently sold his company to Interpublic, said he knew he had one more opportunity to ensure the longevity of his life's work — choosing a successor who cared the same way for the company, its people, its clients, and the Boston community.

During that walk, Sheehan agreed to come back to Hill Holliday as president, then follow Connors as CEO.

The two men seemed opposites. Connors was a larger-than-life character who thrived in the limelight, at times unpredictable. If Connors caught your eye from his office and flagged you down, Sheehan recalled, the evening run you had planned could quickly change into dinner with the prime minister of Ireland.

Sheehan doesn't like surprises. He is a self-described terrible schmoozer, more comfortable in the shadows than the spotlight, where he can sit back and ponder solutions. He recognized that the era of the high-profile CEO was passing, and expanded a team of senior executives to help him run the firm.


Sheehan took over Hill Holliday as the agency and advertising industry entered one of its most challenging periods, with the Internet and later social media undercutting newspaper, television, and other traditional outlets and fracturing mass audiences. Sheehan embraced digital technology early on, developing strategies for ­Facebook, Twitter, and smartphones to build brands.

Take Dunkin' Donuts, for example. Consumers now might be capturing Dunkin' coffee- and doughnut-loving aliens on their smartphone app or flicking flavor icons into moving Dunkin' iced coffee cups to earn points during a game of online Scrabble.

His tenure also spanned the last recession, considered the worst economic downturn since the Great Depression. Even as the US advertising industry cut more than 25,000 jobs, or about 14 percent of employment, Hill Holliday made it through without layoffs.

Sheehan said part of it was luck. The agency didn't have ­accounts with automotive companies, which were hard hit in the downturn, while clients like Dunkin' and Liberty Mutual grew. The rest was old-fashioned hard work to deliver results for clients.

Colleagues describe Sheehan as gracious, funny, quick to laugh at himself, and a great listener, the antithesis of a big ego.

"Really, he's just a kid from Weymouth, still. Which is cool. Thank God," said Lance Jensen, Hill Holliday's chief creative officer.

From his Hill Holliday office on the 35th floor, Sheehan has expansive views of Boston Harbor, the city skyline, and south to Weymouth, where he grew up. He considers himself lucky.

"Being CEO of Hill Holliday could be the best job in Boston," he said. "And I got to do it without having to compromise anything — my values, my family — and never be anything but myself."


Sheehan's local roots and his commitment to the Boston community, either financially or by harnessing the creative resources of Hill Holliday, were among the reasons Connors said he knew Sheehan would be the right successor.

Most recently, Sheehan took a lead role in developing The One Fund Boston to support victims of the Marathon bombings. He came up with the now ubiquitous name, enlisting the people and resources of Hill Holliday to set up the fund's website, design a logo, and develop the early messaging that didn't just raise millions, but created a spirit of community and healing.

"I would describe Mike as the immediate glue that pulled it all together in those first hours," said James Gallagher, executive vice president at John Hancock, the principal sponsor of the Boston Marathon and a Hill Holliday client since the mid-1980s.

Through it all — recessions, new technologies, bombings — Sheehan stayed constant, colleagues said, creating an environment for people to do their best work. "I always wanted Hill Holliday to be a place where you could walk in the door and be yourself," Sheehan said. "That you never had to conform to the conventions that people think advertising people should be. You don't have to be hip, you don't have to be cool."

Sheehan was named CEO on the company's 35th anniversary. On Monday night, Hill Holliday celebrates 45 years with a lavish party. There will be champagne and dancing, though Sheehan won't be found anywhere near the dance floor unless his friend and successor, Kaplan, drags him out there.

As Sheehan steps back, he's still unsure of his next move. He will still make time for family: his wife, Maureen, and their young kids. He adores driving Catherine, 6, and Michael, 4, to school, eavesdropping on their back-seat chatter, or counting Ford and Jeep logos together.

He plans to increase his involvement with the corporate and not-for-profit boards he sits on, from Catholic Charities to Thayer Academy in Braintree to Raptor Accelerator, a Boston firm that develops emerging companies. He'll be more involved with companies in which he's invested, and have the freedom to explore his next move — which, he confirms, won't be running another advertising agency.

"Taking over [Hill Holliday] was a little bit like driving dad's car," Sheehan said. "I was relatively cautious in how I operated because I didn't want to ding it. Maybe in my next iteration it would be fun to drive my own car."