High-tech Exec

Shaun McConnon on the grounds of his home in Wayland, Mass.

Shaun McConnon on the grounds of his home in Wayland, Mass.

Shaun McConnon '66, has become a major force in the technology industry.

This profile is the cover story of the Roanoke Magazine, Issue 2, 2013. See the full issue here.

By David Treadwell

"I bought two coffees - one with milk, one without - and three pastries. What would you like?" asked Shaun McConnon '66, directing me into the kitchen after a quick tour of his home. Nice touch, I thought to myself, not knowing what to expect next from this immensely successful high-tech security entrepreneur. After settling down in the living room, McConnon, with some prompting, began to tell how a man like him got to be a man like him, despite all odds.


McConnon's hardscrabble early days did not foretell a successful life. His father was an only child, orphaned at 16. He served as a Tank Commander lieutenant in Patton's Third Army, 16th Armored Division. He worked in the insurance industry, moving his family around from Brooklyn, N.Y. (where McConnon was born) to Queens to Levittown and, ultimately, to Lynchburg, Va. He was rarely home and, according to McConnon, seldom really present.

McConnon's mother, whom he describes as "pure Czechoslovakian," was the daughter of a coal miner and one of 11 siblings. In the late 1920s, her family was evicted from their home in the company-owned coal-mining town of Shoaf in western Pennsylvania, when John L. Lewis called the famous coal miner's strike.

McConnon's mother and father met under the large globe in Flushing Meadows at the 1939 New York World's Fair, a romantic touch in a union later sorely tested.

McConnon admits that he was a handful as a boy because his father was seldom around. "They sent me off to a Catholic boarding school, where I benefited as much from the context as the education. They took care of me."

McConnon moved with his family to Lynchburg, where he attended E.C. Glass High School his last two years before college.

"My academic performance was good, but not great, and I yearned to leave home. It got so bad in the summer of 1961 that I ran away from home for three months, hitchhiking 800 miles back to New York City at age 16 and staying with friends for almost three months. No one called to ask how I was doing. The experience hardened me, put a chip on my shoulder, and told me that I had to survive in the world on my own, by myself. No one was going to be responsible for me but me. At that point I became a man, somewhat flawed, but a man. Or at least I thought so. I only started growing up at Roanoke College three or four years later."

At E.C. Glass, McConnon softened what he calls his "tough guy New York edge." He ran track, developed good relationships and stabilized himself. After high school, McConnon headed off to a small college in Missouri (Tarkio College), which folded a few years later. Determined to become a veterinarian, McConnon got good grades at Tarkio and later gained acceptance as a transfer into the Class of 1966 at Roanoke.

McConnon's Roanoke years were tumultuous yet growth-inducing. He majored in biology, and minored in chemistry; he tutored classmates in math, biology and chemistry. He loved psychology ("Dr. [Karl W.] Beck was phenomenal.") and history ("Dr. [Harry E.] Poindexter was great."). And he says that English professor Matthew Wise taught him how to write.

McConnon held down several jobs to pay his college bills, as he had no financial support from family after his second year. "I did a little of everything from selling sandwiches in the dorms to working for a firm that delivered the campus laundry and dry cleaning," he said. He also ran track - fast. A top sprinter, he ran anchor on Roanoke's champion 4 x 100 relay team. (Morris Cregger '64, current chairman of Roanoke's Board of Trustees, ran on that same relay team.)

McConnon loved his fraternity, Kappa Alpha Order, but turned down leadership roles. "I was feeling sorry for myself. My loans were piling up, and I didn't want the extra responsibility," he said.

In addition to his personal trials, McConnon shared the uncertainty of college men around the country during those years. "The Vietnam War was raging, and none of us knew where we would be after graduation."  The military rejected him because of his lifelong problem with asthma.

After graduation, McConnon went to work for Wyeth Labs, a pharmaceutical company out of England. For two and a half years he did pharmaceutical research in teratology and toxicology in Paoli, Pa. "Unfortunately, I was allergic to all their lab animals, and after two years, the company transferred me to sales," he said.

The pharmaceutical sales job proved frustrating, but then a friend told him of a job that marked a key turning point in his career.

"RCA was starting a computer division, and they were looking for a person with a degree in science who loved puzzles. That was me!" Indeed, it was. In fact, McConnon had been chess champion at the Catholic school he'd attended.

The computer division faced stiff competition from IBM and was later bought by UNIVAC, later renamed UNISYS.

McConnon didn't get a job with UNISYS, but he was heavily recruited by Honeywell's newly minted computer division. "My new bosses had been former football stars: West Point's kickoff returner and Navy's kicker, two very competitive guys. They liked me, and they taught me everything I needed to know in my early sales career."

From Honeywell, McConnon went to Data General, a competitor of the multimillion-dollar Digital Equipment. McConnon then went on to Sun Microsystems, where he compiled a superb record as New England regional sales manager. "I hired over 200 sales reps and managers, and we kicked some serious competitive butt as we built one of the largest and most competitive high-tech organizations in the U.S."  He then went on to help establish Sun Microsystem's presence in Australia.

After returning to the United States, McConnon launched the next phase of his career: starting, building and selling high-tech security companies, which detect and flag abnormal, suspicious or intrusive activity. He's accomplished this feat not once but three times: Raptor Systems, Okena and Q1 Labs. And he's in the early stages of his fourth start-up: BitSight Technologies.

Goldman Sachs, McConnon's banker for Q1 Labs, gave him a plaque indicating that these three companies had sold for over $1 billion combined, earning the investors a small fortune.

But how? How has Shaun McConnon attained such astounding entrepreneurial success in the fiercely competitive high-tech arena?

McConnon offers his own explanation or, more accurately, his business philosophy: 1. hire the best and the brightest people to build your management team; 2. create a culture that taps your employees' skill sets and helps them thrive; 3. treat people with respect; 4. focus on your competition ruthlessly; 5. raise money when you don't need it, because having a sufficient supply of cash helps the company weather the storms; and 6. be honest and authentic.

McConnon noted that high attrition is a cancer in any business, especially the high-tech industry.  You have to create an environment in which people want to stay with your organization, he said. And that's precisely what he has done.

Tom Turner, currently a vice president of marketing and business partnerships for IBM's security division, worked with McConnon on two of his ventures, and he can explain some secrets to his mentor's success.
"Shaun knows what makes people tick [which  is] a tremendous asset in hiring, managing a team and negotiating. He has an uncanny ability to look into the future of the high-tech industry in order to position a company to be successful. And he's not afraid to fail." When Turner adds that McConnon is "a bit of an Irish rogue as well as an existential businessman," one gets the sense that people like working with McConnon, that the bonds extend deeper than a typical business relationship.

John Egan, a lawyer with Goodwin Procter in Boston, speaks from the perspective of having known McConnon for 20 years. His firm helped take some of McConnon's companies public.

"Shaun is an amazing visionary. Some people can see where the puck is now; he sees where it's going to be in five years. He sets the vision and gets the buy-in from his people. I've seen some great negotiators, and Shaun is the best I've ever seen. His people know that they can trust him and that he has their backs. And he's got a great moral compass; he does what's right."

David Fachetti, a venture capitalist with Globalspan Capital Partners, said McConnon "has all the attributes of the classic entrepreneur: great market intuition, incredible resilience and a positive energy. People want to work with him."

One might think that after creating and selling three companies, McConnon would be content to sail into the sunset or, more likely, down to his second home on Seabrook Island, S.C. One would be wrong. McConnon is currently masterminding another start-up: BitSight Technologies, which, according to its website, "transforms how technology companies manage risk."

"I'm not sure I'd know how to retire," he said, laughing, as he talked about his latest venture. He makes reference to the part in the film "Patton" where Gen. George S. Patton is shaking his fist at the sky and yelling, "They can't have a war without me." McConnon then admits that he shares Patton's furious passion, though on a different battleground; he doesn't think there should be another breakthrough in security technology without him being somewhere on the field, leading the charge.

Passion, to be sure, characterizes other areas of McConnon's life. He and his wife, Bonnie, are major donors to Rosie's Place, a home for battered women and their children, and to the Pine Street Inn, a leading provider of housing for the homeless.

The McConnons also founded Home Away Boston in May, 2012. The nonprofit organization provides free, comfortable housing close to Massachusetts General Hospital for Children for families who come from afar for their children's medical care. Many of these children are cancer patients coming to Boston for six weeks of proton radiation treatments.

As the Home Away website notes, "Our objective is to remove some of the stress of daily living and so enable the families to focus on their child's health and healing." The nonprofit currently offers three one-bedroom units for children (and their families) undergoing treatment. Plans call for expanding to nine residential units and creating a common space to meet the unmet housing and support needs of families coming to Boston for pediatric medical services.

Asked why he feels so strongly about Home Away Boston, McConnon said, "How could I not? I just look at the faces of those kids. They're smiling, while their parents are crying."

Bonnie McConnon added, "It's amazing to see the courage in the faces of the kids with cancer when you know what they're going through."

A chat with Kimberly Sheridan, program manager at Home Away Boston, revealed another side of McConnon's nature. "I worked at a restaurant where Shaun and his wife Bonnie often went, and I got to know them," she explained. "Last spring he asked if I'd be interested in a new position opening up at Home Away Boston, so I took him up on the offer and started in May. He's been very successful, but he believes in the people he picks out. He believes in me, and he's been encouraging me to go to college. Shaun is such a generous man."

Pat Boring, McConnon's sister-in-law and friend for 30 years, said she doesn't know anyone more generous. "He has a great sense of family, and he helps out people in our family without waiting to be asked. He's also the kind of person who keeps up with his friends. You can't say that about too many people these days."

Terry Smith '66, a longtime friend and a fellow member of Kappa Alpha, said McConnon, "was a brilliant student, so he didn't have to study much. But he still took full advantage of the activities." Smith recalled that as a member of the fraternity's "Ways and Means" committee, McConnon was the guy who made sure that if the beer ran out, more beer magically arrived, quite possibly from another fraternity.

When asked to explain McConnon's business success, Smith said, "He's got a magnetic personality. People just like being around him. He's got that authoritarian air. When he talks, people listen."

McConnon came to realize, later in life, the tremendous impact Roanoke College made on him beyond the deep ties with his college friends. "I had deluded myself into thinking that I was just a self-made person, but the more I thought about it, the more I appreciated what Roanoke did for me. I owe a lot to that place."

Jack Hills, a development professional who is former vice president for Resource Development at Roanoke and a current consultant to the College, was the person who reconnected McConnon with the College. "I knocked on his door in Wayland a little over two years ago. We had an incredible conversation, and he wouldn't let me leave. He got tears in his eyes when he started talking about what Roanoke College meant to him. He's remarkable."

"Shaun has a big vision, but he can also listen. He's a leader, but he can also follow," Hills said.

That meeting led to a visit to Roanoke and, in short order, a seat on the College's Board of Trustees in 2012.
President Michael Maxey said he appreciates the wisdom and insight that McConnon brings to the Board.

 "Shaun is a big-picture guy, always thinking about possibilities. He creates a sense of urgency in a good way. He's persistent, but not stubborn. I'm awed by the vastness of his intellect. He's a great example of the lifelong value of a liberal arts education."
McConnon has already had some productive brainstorming sessions with Maxey and other trustees about the challenges and opportunities facing Roanoke College. It's a safe bet that Roanoke will be an even better place in the future because of his great vision, keen intellect and deep devotion to the College.


After we concluded our conversation, Shaun McConnon showed me around the grounds behind his home. I commented on the beauty of the landscaping, and he noted that he had picked out every plant and bush and tree. Somehow, it didn't surprise me that he has a natural gift for spotting beauty in plant life as well as talent in people. He also showed me the serene spot he had created in a rise among the trees for his mother, who liked to sit there in her final years.
When asked about his hobbies, McConnon said that he liked to write. And he takes writing seriously. He recently finished a science fiction novel, "Prophecy," which he's sent off to a publisher in New York City. He gave me a few chapters to read, which I found highly imaginative and visionary.
During our visit, McConnon had spoken proudly of his two sons, Matt, a successful salesman with IBM and accomplished athlete, and Ian, who has a Ph.D. in French Literature from the University of Pennsylvania and is a classical musician.
As he ushered me through the living room, McConnon pointed to a Steinway grand piano. He said he had given it as a surprise to his son Ian. "I wrapped a ribbon around it, and he burst into tears when he saw it. I really miss listening to him play."

- David Treadwell is a Maine writer who specializes in writing for colleges and universities throughout the United States. He has worked on numerous writing projects for Roanoke College over the years and sings the College's praises to whomever will listen.

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