In 2010, Tilly Gray, pregnant with her first child, took maternity leave. The timing could not have been worse: the seventh-year associate at Cassels Brock & Blackwell LLP would be up for partner over the next year. And so, when the firm determined which associates to admit to the partnership, Gray would be at home.
Her performance as an associate had been impeccable. Over the previous half-decade, she had helped grow the firm’s financial-services group from a three-lawyer backwater into a 15-lawyer juggernaut. And, within that practice group, she had established herself as a top sports-franchise lawyer, representing hockey organizations such as the Ottawa Senators. “I loved the team we built,” she recalls. “We were close friends, all in it together. It became my passion.”
In the middle of her maternity leave, Gray went into the office for her annual performance review. That’s when she received the verdict: the firm had decided not to make her a partner. “I was heartbroken,” she says. “Totally crushed.”
More bad news was coming. By the end of her leave, the financial-services group had lost seven of its 15 lawyers. “Every time the phone rang, I was, like, ‘No! No! Not another one!’” says Gray. “There was no single explanation. For instance, a couple of people moved to other firms and a few went in-house. There was one termination.”
Drained of all motivation, Gray decided to leave the firm. “Everything had gone to crap,” she says. “I didn’t have the bandwidth to both rebuild that group and try to get across the partnership finish line.”
But in that same year, before Gray could make her departure official, she received a surprising call. It was Mark Young, who was the managing partner at the time. “We can find you a new role,” he told her. He asked Gray to join the practice-support team, which, among other things, maintains the firm’s database of useful precedents.
Over the next seven years, Gray excelled on that team. “There’s a tendency for people in those roles to not get the respect they deserve,” says Kristin Taylor, the firm’s deputy managing partner. “Tilly was an exception. As a capable and proactive lawyer, she had the respect of her colleagues.”
Gray also took advantage of the lighter workload. “That job allowed me to dedicate more time to building a family,” she says. Gray and her husband, Matthew Dewar, a partner at Levitt LLP, have three young boys at home. All told, she built a great life. But one career goal remained unfulfilled.
“I still wanted to be a partner,” says Gray. “Now, in fairness to the firm, I never had the bravery to ask for it. I wasn’t able to say, ‘Can partnership look different?’ I just couldn’t see how it could still happen.”
In 2017, Gray had another pivotal conversation with Young. He was stepping down as managing partner to head up a new innovation team, whose mandate it would be to streamline the firm’s transactional work with cutting-edge technology. “I needed someone to take the lead with me on the project,” recalls Young. “I couldn’t think of anyone better than Tilly.”
Once again, Gray accepted his offer and took her career to a new level. Her job was, in the main, to boost efficiency. One of her early achievements was to help the real estate group adopt new software that would simplify the many stages of a deal. “Everyone is afraid of change,” says Young. “But Tilly does a great job transitioning our firm to new processes.”
Gray started to meet with potential clients, explaining how the firm could complete transactions faster and cheaper than its competitors. “I was back to being a revenue generator,” she says. “I was no longer a cost centre.” That was a powerful realization. If she could regularly land new clients, then maybe — just maybe — she could persuade the firm to make her a partner. So, in the summer of 2018, she met with Taylor and pitched her on the idea.
Taylor, who had always been impressed with Gray’s talent, became her champion. “To be honest, I didn’t know that she wanted to be a partner,” says Taylor. “But once I understood that it was her ultimate goal, I was able to give her support.” Taylor asked the firm’s top brass to make Gray a full-fledged partner.
Then it happened. In January, after 15 years at Cassels Brock, Gray became an official partner at the firm. “It was an incredible moment,” she says. “I went off the partnership track and fought my way back. I hope that my story is inspiring.”
Timeline of a Bay Street Partner
1994: At 20, Gray leaves North Bay, Ont., to start her undergraduate career at Laurentian University. “I quickly failed out of chemistry,” she says. “I ended up studying English and religion.”
1999: One of Gray’s friends decides to write the LSAT. While studying for the exam, she makes an offhand remark to Gray: “You wouldn’t be able to write this test. It’s not for you.” Taken aback by the insult, Gray is determined to prove her friend wrong. “I don’t like it when someone says I can’t do something,” says Gray. “If she could write the LSAT, then so could I.”
2000: Gray starts law school at Queen’s University. “The whole Bay Street machine kicked into action,” she says. “It swept me up.”
2003: Gray articles at Cassels Brock & Blackwell LLP.
2004: After getting hired back, she joins the firm’s financial-services group. “It was such a pleasure to work on that team.”
2011: She learns she won’t be making partner. Instead, she becomes a practice-support lawyer.
2015: Four years later, Gray is named the director of the practice-support team.
2018: Gray is promoted to director of transaction services, a key role in the firm’s innovation strategy.
2019: After 15 long years at the firm, Gray finally makes partner. “If you work really hard, never throw in the towel.”
This story is from our Summer 2019 Issue.
Photography by Nick Wong