Beyond the Safe Bet
By any measure, Brooke Hilton’s path into the gaming industry has been unconventional. Now head of casino at PointsBet Canada, she has built a career by choosing discomfort over certainty and momentum over safety—especially when staying put might have looked like the sensible choice.
Hilton spent eight years working at the British Columbia Lottery Corp. (BCLC), a chapter she describes as genuinely formative. It offered structure, experience and a clear career track. But over time, something shifted. Her ambitions began to outgrow the role, even before she was willing to say it out loud.
“The biggest decision that shaped where I am today was learning to recognize when I’d squeezed all the juice out of the lemon, and having the guts to move before waiting for it to feel comfortable,” she says. For Hilton, the real risk wasn’t leaving; it was staying. “That gap between knowing and acting is where most people get stuck.”
As a woman in a traditionally risk-averse professional culture, she was keenly aware of how often women are encouraged to choose the safe, predictable option. Instead, saying yes to the next opportunity, she shifted to iGaming. That decision was a launchpad for the steep growth curve that followed.
Hilton’s willingness to step into the unknown would define the next phase of her career. While many industry professionals travel with teams to major iGaming events, Hilton built her reputation largely on her own. She booked packed schedules of meetings and receptions, walked into rooms where she knew no one and refused to let herself shrink from the moment.
“What I’m most proud of is something that doesn’t show up on my resume—I taught myself to walk into a room alone and own it,” she says. With no one to lean on or deflect to, she was forced to become, in her words, “the master of my own destiny.”
It also taught her a subtler skill: being comfortable not having all the answers. In a sector where each market has its own regulations, quirks and culture, and where gaming itself spans countless verticals and specialties, she learned quickly that expertise is relative. “Nobody knows everything,” she says. “The skill isn’t having all the answers; it’s being willing to sit in the room anyway, ask questions and build the relationship. Because at the end of the day, this industry runs on relationships, not resumes.”
Today, at PointsBet Canada, Hilton sits at the center of an industry that has evolved rapidly around her. One of the most significant shifts she sees is the normalization of remote work and distributed teams. What was once a geographically constrained industry with hubs in places like London, Malta, Gibraltar and New Jersey has opened its doors far wider.
“The widespread vote of confidence in remote work—and hiring the right person for the job regardless of where they live—has opened doors that simply didn’t exist years ago,” she notes. That shift, combined with the growing fluidity between operator and business-to-business roles, has expanded the career opportunities for emerging leaders. “Lateral moves between B2C and B2B can be some of the most meaningful career-building moves you make, and there are significantly more diverse and remote roles available industry-wide than there used to be.”
Inside PointsBet Canada, Hilton credits the culture—and specifically the behavior modeled at the top—with accelerating her development. CEO Scott Vanderwel has been an essential mentor and role model, not only for what he teaches but for the challenges he hands her.
“He’s pushed me to look at problems from a different vantage point, at a leadership level, before I necessarily felt ready for that seat,” she says. By trusting her with ambiguous and high-stakes work, Vanderwel signaled that she belonged in those conversations. That trust, Hilton believes, did more for her growth than any formal program could.
“What’s been invaluable to me at PointsBet Canada is having leadership that demonstrates strong character and does the right thing, even when it’s not convenient and doesn’t come with an immediate reward,” she adds. For her, that distinction, between companies that talk about developing leaders and those that quietly model it, is everything.
Her advice to those coming up behind her reflects the choices that defined her own career. Don’t wait until a role feels perfectly safe. Learn to recognize when you’ve outgrown your current seat and have the courage to move before comfort catches up. Put yourself in rooms where you’re not the expert. Treat every conference and meeting as an opportunity to build real, long-term relationships, not just exchange business cards.
And perhaps most importantly, look closely at how your leaders behave when things are hard. “Leadership isn’t just what’s written in a values deck, but what’s modeled when nothing easy is on the table,” Hilton says.
As she looks ahead, Hilton sees an industry that remains both global and surprisingly intimate—a place where careers can be built from anywhere and where talent and character travel further than a postal code. For those willing to bet on themselves before they feel ready, she believes the future of iGaming is wide open.
—Kevin Dennis is senior vice president, Canada, for The Innovation Group
