Ask Jackie Doak for a single piece of advice for women pursuing business careers, and she can’t do it. Instead, she’ll give you half a dozen.
She seems to have a difficult time containing the host of ideas blowing through her mind.
Doak, 51, the president of Dart Real Estate, is one of the Cayman Islands’ most prominent businesswomen. She oversees the property development at Kimpton Seafire Resort and Spa and has guided the development of Camana Bay, where her offices are located, since its inception. With her success has come some perspective and some principles she tries to follow.
“Every woman should have a goal and an aspiration that speaks to their purpose. Each and every day, they should make decisions that move them toward that goal.”
Goals can change. Doak, herself, has had three different careers. She began her professional life as an attorney after graduating from Fredric G. Levin College of Law at the University of Florida. Doak spent nearly two years at Carlton Fields, a Tampa-based law firm, working in commercial litigation. She said she not only liked the job, but the process of becoming an attorney.
“I thoroughly enjoyed law school,” Doak said. “I love the analytical thinking, the challenging thinking, the Socratic method. I love researching. I can get consumed.”
She got a little too consumed, she admits, but felt she had found her place.
Then came an unplanned turn in her road.
Her father had owned an office supply store in the Cayman Islands – Doak grew up here until moving to Florida in her high school years – since the 1970s. He needed help and asked her to take a one-year detour in her legal career. She agreed, and returned to Grand Cayman in 1993.
“I have not been back,” she said.
Her next career change came in 2002, when she and her husband, John, an architect, had their first child. Doak said she began looking for job opportunities that would allow time for family.
“What consumes me now is being able to integrate and balance work life, to be present, whether it’s with family or with work.”
Doak said she is fortunate to have her children nearby during the workday. They attend Cayman International School, which is in the Camana Bay complex. Occasionally, she will see them outside her office window, trooping off on a field trip.
“I could run out that front door and give my son and daughter a big hug,” she said.
Their connection with Camana Bay, she said, gives them a better understanding of her job. That makes it easier when work pulls her away from home for a conference or an off-island meeting.
When it’s time for family, she does her best to make sure her focus is there, she said. On vacations, that sometimes means locking her cellphone in the hotel room safe.
“You consciously try to put the phone and work down, and separate yourself,” she said.
“It’s all about how you make people feel and … how you treat them.”
Bringing a personal touch into the workplace is important,” Doak said.
“My grandfather was chairman of Wimbledon (tennis tournament),” she said. “He really was instrumental in many of the things that I do today. He taught me the importance of that personal connection.”
He wrote personal letters to anyone connected with Wimbledon, she said. Last year, Doak did the same. She spent four days during her Christmas holiday, writing individual notes to the 124 members of her team at Dart.
“It’s important to me for my team to know how much I value them,” she said.
Anna Wootton, the company’s public relations manager, said employees were surprised to find the notes on their desks on the first day they returned after the new year.
“It’s a moment of light,” Wootton said. “It’s nice to feel that personal touch.”
Many employees still have the notes pinned to their cubicle walls, Wootton said.
Gabrielle Wheaton, senior executive coordinator, serves as Doak’s right-hand woman. She said her boss’s ability to connect with people is critical to the way the company does business.
“Jackie is very much about putting the right person in the right position,” Wheaton said. “She’s about finding the best way to make things work.”
Often, she said, Doak sees things in others they may not see themselves.
“She is very good at seeing that someone is capable of something and just needs a nudge in that direction,” Wheaton said. “That’s part of the reason I have this position. I wasn’t sure if I was ready for it. She was the one that said, ‘No, you can do this.’”
Wheaton was talking at the end of her second week in her new position. But she said she is convinced Doak was right in her assessment. “The learning never stops.”
Learning can come from many different sources, Doak said. The more sources, the better.
“An area that I have focused on in the last five years was inclusiveness in the decision making process,” Doak said.
As a woman in business, she said, she has a particular appreciation for diversity in the workplace.
“The development and construction world has been very male dominated,” she said. “I have attended meetings with U.S.-based development companies, where I am the only woman in the room.”
That is not the case so much in the Cayman Islands, she said, where there are many examples of women in leadership roles, both in business and in government.
“At Dart, we have an exceptional group of women leaders,” she said. “One of the [company’s] values is meritocracy. Both women and men become leaders based on their skills and experience. As a result, different points of view are brought to the table and positively influence the decision-making process.”Wheaton said other women around Doak appreciate that.
“I am old enough that I grew up in an era where women were fighting to be recognized,” said Wheaton, 46. “We know there are still issues with gender equality and pay equality. It’s hard to let that go and not say, ‘Can I really achieve the same as a man?’ But working with Jackie, it’s not really even a question.”
“I would encourage laughter, don’t take it too seriously.”
Doak said she looks for opportunities to bring levity into the workplace. She does daily walkabouts through the office, typically in the morning, in an effort to help energize her employees.
“I make observations, say something loud, tell a joke, jump into meetings,” she said.
She said she also enjoys walking the campus of Camana Bay, seeing what has been accomplished in the past 10 years and appreciating it. That includes the facility’s fountains, which sometimes play a role in maintaining her perspective and keeping things light.
“I’ve been known to run through them.”