One May morning in 2017, just weeks after her 56th birthday, Bradley & Parker Chief Executive Wynne Nowland hit ‘send’ on an email to the insurance broker’s workforce. It was no routine memo.
“I am writing to tell you about a matter that is essentially personal but will result in some changes at work,” she began. After a lifetime living as a man named Wayne but hiding her true self, she wrote, “I will be transitioning my gender.” She emphasized that she intended to keep leading the firm she had helped build over 30 years, then added: “In fact, I may be less distracted when I no longer have two personas to juggle!” Two hours later, she was met with hugs—and some wide eyes—from some of Bradley & Parker’s 70 employees as she arrived at its Long Island headquarters in a woman’s pantsuit, pearls and full makeup.
Across America, an estimated 1.4 million U.S. adults are transgender— double the number a decade before, according to a University of California, Los Angeles, analysis of government data—and more are coming out on the job. Far fewer have done it while leading a company. Not only has Ms. Nowland had to find support for her transformation in the workplace; she’s had to guide her employees, her board and a number of Bradley & Parker’s thousands of corporate clients through it.
Karen Weber, the firm’s vice president of operations, said the move made her respect Ms. Nowland even more, but she worried at first how some top salespeople and clients would react. “Insurance is a really conservative business,” she said.
Jonathan Carroll is vice president of business development and a member of Bradley & Parker’s executive team who had formed a close friendship with Ms. Nowland over the years. He said his immediate reaction to her news was discomfort. He struggled at first to use her female pronouns. “I had never met a transgender person before or known someone going through that transition,” he said, adding that he quickly got over it. “How sad would it be for someone to have to live in hiding of who they are.” Mr. Carroll came to Ms. Nowland’s defense at a networking event a few months later when another man began cracking jokes about her. “I finally had to grab the guy by the shoulders and said, ‘Dude, you’re talking about my boss. Please stop. You’re making me uncomfortable,’ ” he said.
Among some of the female staff, a big question was which bathroom Ms. Nowland would use. A few women approached Ms. Weber worried that because Ms. Nowland was tall, she could see over the stalls. “It was more a nervous question, not an HR inquiry,” Ms. Weber said. She informed them that Wynne would use the restroom that matched her gender identity: the ladies’. “I’m not saying they were jumping for joy at first, but no one said anything again,” Ms. Weber said.
Ms. Nowland’s experience reflects both the complexities of being transgender at work and the solitary nature of being a leader managing a business through any major change. While the Supreme Court ruled in June that workplace discrimination of transgender people is prohibited under federal civil-rights law, and New York already provided legal protections, the onus remained on Ms. Nowland, as CEO, to get her company and customers behind her. “It’s great to be a leader, but if the troops refuse to be led, you know you can’t,” she said from her office, which is adorned with a photo of her before her transition, with her father, and a plaque, given to her by a staff member, engraved with the words “BOSS LADY.”
That’s required diplomacy, humor and preparation for those who might not welcome this news. Before a pitch meeting planned with a potential client early this year, a representative from the other side asked that Ms. Nowland not attend. Ms. Nowland agreed so her team might have a better shot at clinching the deal. (The meeting never materialized once the pandemic struck.) Ms. Nowland is aware her position, and affluence, have made her transition much easier than for many transgender people.
Raised in a conservative Irish-Catholic family and educated at an all-boy high school, Ms. Nowland remembers feeling inner conflict while growing up. But she said she learned early on to wall off her confusion and discomfort, an ability she said helped her achieve career success. At 25, she joined Bradley & Parker and soon after scored her first major coup, winning the national Dunkin’ Donuts franchise account. Channeling the energy behind her private turmoil into work helped. “I worked ridiculous hours,” she said.
But as the years passed and one, then another, marriage fell apart, the dissonance between her inner self and public persona chafed more. Growing public attention on transgender people— particularly the 2015 transition of Caitlyn Jenner—prodded her to consider a different way. “It went from, ‘I’m just fated to be this way,’ to, ‘Well, wait, this could happen,’ and then, ‘It should happen,’ ” she said. By then, it was 2016 and Ms. Nowland, then COO, was slated to take over as CEO the next January. As she began to quietly carry out her transformation—applying to change her birth certificate and arranging to have a couple of surgeries— she was settling into the new role. Her big concern was what it would mean for the firm.
“I didn’t want something that was going to be gratifying to me to be at the expense of the company and the people that work there,” she said. She told the board and a few other executives
about a week before making it official. Ms. Nowland also wanted to make sure, in particular, a few big clients she personally dealt with were on board. One was Charles Gamarekian, founder and CEO of New Jerseybased paving stone and outdoor-wall manufacturer Cambridge Pavers. The day after Ms. Nowland sent the email to her staff, she emailed him about her transition, too. Seven minutes later, her computer pinged with his reply: “I applaud you and our business and personal relationship can only grow stronger.” The next day a bottle of Dom Pérignon arrived at her office from him.
Wynne Nowland at her office in August, and on the day in 2017 she announced her transition, below.
“Two things came to mind: what a struggle she must have had for so long, and what it must have been to write this email,” Mr. Gamarekian said, adding that over the years he had come to value Ms. Nowland’s advice, including her encouraging him to expand during the last recession. “I just wanted her surrounded with joy and happiness.” The company said it isn’t aware that it’s lost any clients because of Ms. Nowland’s transition. Since 2017, Bradley & Parker’s revenues have climbed 20%. Since her transition, colleagues describe Ms. Nowland as more at ease. Toni Glagau, whom Ms. Nowland promoted three years ago when she was 25, considered her a mentor before the transition, but found it easier to confide in her about being such a young manager afterward.
“When she transitioned, I saw she’s going through something where she’s different, too,” Ms. Glagau said. “It made it easier to see how she could relate.” ‘It’s great to be a leader, but if the troops refuse to be led, you know you can’t,’ Ms. Nowland said.
