Sean McDermott

Now is the Time

At the bedside of his father-in-law the night before he passed away, Sean McDermott saw what it meant to live a fulfilling life. His father-in-law had been tremendously successful, selling his business at age 55 and remaining remarkably active until he fell ill with cancer. Through it all, he was a loving family man, and when Sean asked him if he had any regrets, he said he only wished that he could see his grandchildren grow up. “That was a very defining moment for me in recognizing what was important to me as a person,” Sean remembers today.

The epiphany came three days after Sean had been let go from his job—a sequence of events that unlocked in him an inner resolve to say, “Now is the time.” He always knew he would start his own business, but some might have argued that the wake of his father-in-law’s death was not the time to do it. His wife, Susan, was working through her grief, and the family had a house and a mortgage to pay off. But when he told Susan he thought he should take the leap, she saw the tremendous potential in her husband’s will and supported the idea. “Seeing how much my father-in-law had accomplished and how content he was on his deathbed really gave me new confidence,” he says. “I decided to follow this path where I could control my own destiny, make my own decisions, and ultimately be able to say, I did everything I wanted to do.”

With that, Sean founded Windward IT Solutions, a hundred-employee-strong consulting firm that specializes in helping Fortune 500 companies and the DoD manage complex, global networks and data centers, making their businesses leaner and more competitive. The firm has evolved greatly since its inception in 1997, and so has Sean’s outlook on leadership.

“I’ve learned along the way that companies, like their founders, go through a maturation process,” he reflects today. “After the excitement of the initial building process, with lots of risks and unknowns but free reign to do what needs to be done, founders can fall into the rut of the day-to-day grind. As it becomes more stable, a company acquires more bureaucracy and processes. That’s important for the long-term growth of the company, but it can also be stifling. That’s why it’s so important for the CEO to continue to create.”

Sean took a hiatus from Windward in 2004 to launch another business, RealOps—an avenue by which he could enter another major phase of personal creativity that he craved. RealOps was a true startup in every sense of the word. There, he built software from scratch, raised venture capital, and took the product to market. The RealOps software, incubated within Windward, was a set of predesigned code that could increase efficiency in implementing and automating IT processes. “For three years, I was running around, raising money, talking to investors, and building customers in New York and California,” Sean recounts. “It was an exciting time, and the team was really energized.” When he sold RealOps in 2007 to BMC, a multi-million dollar management software company, he stayed on for a year and learned how to survive and thrive in that new large company environment.

When Sean returned to the helm of Windward in 2009, he struggled at first, missing the thrill of building something new. But he soon realized that Windward would need to evolve to meet the challenges it faced in the marketplace, and that his creative energies could be used to formulate and implement strategies to make those changes. “I started looking at the services we were taking to market, how people perceived us, what markets we could go after, what our messaging and marketing platform should be, and how we could restructure the organization accordingly,” Sean says. “It got me into creative mode—the mode I find most fulfilling.”

Now, Sean strikes a balance between growing the company and keeping his creative currents flowing by envisioning what Windward needs to look like in three years, and what needs to be done now in order to get there. Keeping the company at the industry’s forefront while also keeping Sean engaged takes innovative efforts today, even if they may not come to fruition until months down the road. Bringing strategic thinkers onboard has helped advance the dialogue within the company, and Sean is always looking at how new markets, capabilities, and investments can advance the company’s goals.

This focused approach is built on the belief that success is garnered from stepping beyond one’s comfort zone—a philosophy Sean embraced as a young boy growing up in Ankara, Turkey. He was born in Washington, D.C., but his father was a cryptologist for the National Security Agency, prompting the family to move overseas when he was nine. “Every year, at the end of Ramadan, the residents in Ankara would slaughter sheep in the courtyards,” he says. “It’s one of my most vivid memories. There was a lot of poverty, and life was lived very differently. My time there changed the way I saw the world. I came to understand that opportunity isn’t a given, and that it’s incredibly important to get out of your comfort zone and experience other ways of life.”

The McDermotts returned to the D.C. area when Sean was twelve. The youngest of four children, he was always considered a responsible child. His mother, a homemaker, was a skilled painter and sculptor who started her own interior design business. She inspired Sean’s lifelong penchant for creativity, to the point that he worked one-on-one with his art teacher in high school, won creative awards, and considered pursuing art in college. That creative leaning, paired with the intelligence cultivated in him by his father, made for an unusually effective mind for business.

Sean earned his first wages when he took over his brother’s paper route. He got a job at a pizza place by the age of fifteen and has worked every day since then. When he was laid off from that job, he was hired at an even better pizza restaurant—his first lesson that seemingly bad situations can lead to far better outcomes. Whether he was roofing houses or working at gas stations, Sean was always working multiple jobs at once.

Through high school, Sean watched his father buy and run a woodworking business in Annapolis, which he eventually sold. He risked a lot and lost a lot, but he went back to work after his entrepreneurial venture, built back up his wealth, and ultimately retired well. “His example showed me that it’s possible to rebuild your life after adversity,” Sean remembers. “The stress was hard on him, but I have a lot of good memories of how my parents got through that hard time. I saw him get knocked down and get back up, never giving up or feeling sorry for himself. I also saw him run his own business and be his own boss, and I wanted to be like that.”

Sean’s father had picked himself back up by working as a program manager at General Electric’s Valley Forge Space Center in Philadelphia, where he built satellites for government agencies. When Sean began college at Villanova University, he was inspired to study mechanical engineering in part by his father’s work, and in part by the drafting and design that the field entailed. He soon realized, however, that the theories and minutiae of the work didn’t interest him, so he switched to electrical engineering instead, which Sean saw as more versatile.

Though he made Deans List both semesters of his senior year, he struggled substantially with the dense material and stiff teaching style. “Looking back, I think that a lot of the challenges I faced revolved around how I was being taught,” he recounts. “I don’t do well with lecturing; I’m a hands-on learner, but there wasn’t much of that back then. My father had every opportunity to come down on me hard for my performance, but instead he was very supportive, and that’s stuck with me. He tried to understand the issues and challenges before he reacted, and I try to act with that level of patience now.”

Sean worked for a small company during his first year out of college and was then hired by the telecommunications division of the Department of Justice. “I didn’t even know what telecommunications was, but accepting that job was one of the best decisions of my life,” he recalls. It was the early 1990s, and with the explosion of the internet on its horizon, telecom became the fastest growing industry in the last hundred years. “That job landed me in the field that defines my success today,” he says. “It was pure luck.”

After four years of working with various telecom networks in that capacity, Sean decided he wanted to start his own consulting company, but his specialized expertise caught the eye of the consulting firm Booz Allen Hamilton. He accepted a job with the large firm because he knew it would better prepare him to pursue his entrepreneurial ambitions. The job entailed an education all its own, and Sean mastered the craft of proposal writing and deliverables. He learned how to run teams more effectively, how to build companies, and how to close new business. “They gave me world-class training, and I would not be where I am today if it weren’t for that experience,” he affirms. “They gave me opportunities and held me to an incredibly high standard. If you’re up for it, you can use that kind of experience and come out a totally different person.”

When Sean decided to resign in 1996, his boss was not surprised. At Booz Allen, employees of Sean’s caliber either become partner or leave to start their own successful companies. Before starting his own business, however, Sean made a pit stop at a small company that was thrilled about the processes and skills he brought from his previous work experience. But the company’s culture was marred by power brokering and positioning that ultimately led to his termination—the humbling experience that prompted him to hop in the car and drive to his ailing father-in-law. Several years later, the company’s senior leadership pitched the idea of a merger, which would make Sean CEO of the new company. However, by then he had already brought Windward to stable ground and was poised to launch RealOps.

When Sean and Susan agreed that starting Windward was a good idea, they said “yes” to entrepreneurship with no idea of what that agreement entailed. He started the business at the beginning of the internet boom and grew it to 125 employees in four years. “I tell my kids that it takes a lot of hard work to put yourself in a position where you can have good luck,” he explains. “You make these decisions about the unknown with no clue about what the future holds for you, and it definitely hasn’t been roses all along. Though the company went through several very hard times, once you make your bed, you’re in it for the long haul, unless you say you’re done. But I’m not one to give up. So much of business is about working hard to put yourself in a position where, if something good happens, you can take advantage of it.”

Over the years, Sean has come to find that the most important challenge of leadership is communicating a vision that compels a team to go all-in on that organization’s mission. This he accomplishes in part by making prompt decisions and trusting his instincts. “The biggest thing I’ve learned about leadership is that, sometimes, you just have to follow your gut and do what you know is right,” he says. “My family’s health and our unity are very important to me, but most business aspects are fluid. You need to get over them and move on, so take action and don’t agonize too long.”

In advising young people entering the working world today, Sean emphasizes the importance of being a sponge and absorbing as much as possible. “To this day, I ask people for their opinions because I know I don’t know everything,” he explains. “I’m still learning. There are so many opportunities to learn from people, experiences, and most of all, mistakes. Fail, learn from it, and move on. As long as you take the time to really reflect, you learn more from failing than you do from winning.”

Sean’s own commitment to learn from mistakes and engage in a lifelong pursuit of success landed him the 2009 Professional Achievement Award from his alma mater, Villanova. And now, to connect more deeply with the local community, he is one of the founding members of the board of the Medical Children’s Charitable Partnership Foundation, which provides medical care to underprivileged children in Fairfax County, Virginia. He is also on the Board of Advisors at Villanova’s College of Engineering, helping to build entrepreneurial skills and business acumen within the organizations. As a company, Windward participates in an array of volunteer work with the Ronald McDonald House, Habitat for Humanity, soup kitchens, and Toys for Tots. It is in the process of pivoting to a single, more unified focus.

This demonstrates a company culture that embraces hard work while prioritizing the things in life that are most important, like community and family—values that are evident in Sean’s own life as well. In times past, he traveled frequently for work because very few of Windward’s customers are local. Then, while working for BMC, he ran a  $200 million unit and flew around the world, frequenting locations like London, Amsterdam, Singapore, and Australia. When he resigned to return to Windward, the CEO offered him a worldwide senior leadership position, but Sean wanted to watch his three daughters grow up. “My perspective has really changed over the years,” he remarks. “I still love to travel, but now, I focus on doing that with my family. Susan and I both grew up with rich memories of traveling with our families, and we want our kids to have that. It’s those memories and photographs that I cherish most. I think success is measured not just in business, but in life, and Susan and I have a great family.”

Whether in building a family or building a company, Sean is most at home and most alive when he’s in creation mode, and his success is about channeling that creativity even amidst stabilization and security. It takes real courage and creativity to take that first entrepreneurial leap and make something out of nothing, but it takes commitment and even more creativity to make that something into something better. “It’s important for entrepreneurs to transition their companies from the beginning startup phase into a more operational phase, without losing that excitement and creative spark,” he says. “It’s easy to fall into a rut, but it’s also easy to get out of one. Because we’re creating again, I’m more excited about Windward than I have been in years.” Indeed, if we are to find ourselves at the end of our lives with no regrets, we must continue to see fresh starts with each turn, and continue to say, “Now is the time.”

Sean McDermott

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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