The common thread throughout Anna Martini’s prolific career? Fun.
“Having fun is really important in everything I do,” Martini shares. “If it’s not going to be fun, then I don’t think anybody should be doing it.”
But don’t get it twisted—Martini knows that fun is just one piece of the puzzle and keeps her eye on the prize. Hard work, focus, and knowing the key drivers of a business are essential, too. As CEO of global menswear brand Psycho Bunny, she strikes a balance between playfulness and precision.
“Successful people work hard,” she asserts. “I want to demystify this for anybody who thinks otherwise. But the secret is finding joy in what you’re doing—essentially in everything you do.”
Martini finds joy in her current role with Psycho Bunny, a brand rooted in high-quality craftsmanship, bold design, and audacious style. It’s a company where she can flex her business muscles and cultivate team spirit.
Founded in 2005 in New York City, Psycho Bunny has grown into a global powerhouse with over 100 stores worldwide, spanning North America, Latin America, the UAE, Japan, and South Africa. Known for its premium Pima cotton polos and iconic bunny logo (4,000 stitches go into sewing every embroidered bunny), the brand also has a strong wholesale presence in retailers like Bloomingdale’s, Nordstrom, Dillard’s, and Harry Rosen.
Psycho Bunny’s partnerships with Roblox and Tennis Canada showcase its dynamic spirit. From a sold-out Summer Splash Storefront in Roblox to becoming the official athletic apparel sponsor of Canada’s tennis teams, these initiatives represent the types of playgrounds that align with the brand’s magnetic consumer.
Today, Psycho Bunny delivers a premium experience through its tagline, The Bold Standard, an homage to confidence, sophistication, individuality, and self-expression. It’s an attitude and a state of mind.
At the heart of this ethos is the brand’s target psychographic—a confident, bold guy with a winning approach to life.
“He’s magnetic and commands attention, exuding energy and character.” Martini adds. “He has joie de vivre and he’s bold, with a hint of mischief.”
Psycho Bunny’s boldness is a natural fit for Martini, whose career has been marked by individuality and fearless leadership.
I sat down with Martini at Psycho Bunny’s Montreal HQ to explore her approach to leadership—using your voice in male-dominated industries, leading a corporation with the strategy of a sports team, and embracing vulnerability as a strength.
What stood out most in our compelling conversation? Martini’s ability to navigate and thrive in male-dominated arenas—spanning Deloitte, the Montreal Canadiens, and now a menswear brand—and how those experiences have uniquely prepared her for her current role. Throughout her career, she has remained unapologetically herself.
“I’ve always been colorful, both literally and figuratively,” she says, reflecting on her time as a partner at Deloitte in the ‘80s and ‘90s. “Back then, it was a conservative environment—very suit-and-tie. But I didn’t fit the mold, and I didn’t try to. I don’t think I even owned a navy suit!”
Her boldness extended beyond her wardrobe. Martini advocated for gender equity in leadership, challenging her colleagues to promote women and develop future female leaders. “I started conversations about how we could coach women and create better representation in professional services,” she shares.
“Even in a male-dominated space, you need to be true to yourself. Don’t dim your light,” Martini advises.
As Executive Vice-President and CFO of the Montreal Canadiens, she gained invaluable insights into teamwork and business strategy.
“There’s the world of sports, which is about winning games. And then there’s the business side,” Martini says. “From selling tickets to creating partnerships, the parallels with retail were clear to me.”
Her time with the Canadiens shaped her leadership approach, emphasizing the importance of building strong teams and learning from different perspectives. “As a leader, your job is to make people successful. That’s it,” she says. “You need to surround yourself with the right people and set them up for success.”
Martini’s pivot from retail (as President of Groupe Dynamite Inc., after nearly 2o years at Deloitte) to hockey wasn’t without its challenges. Entering a male-dominated industry, she embraced vulnerability as a strength.
“When I started, I acknowledged what I didn’t know,” she recalls. “I needed to learn the key drivers of the business and understand how it operated. You have to be vulnerable enough to admit what you don’t know while leaning on your expertise to add value.”
For Martini, vulnerability builds trust and fosters collaboration. “Great leaders use vulnerability as a superpower,” she says.
A champion of giving back, Martini prioritizes mentoring the next generation. She regularly speaks to business students at McGill University and has established a bursary for accounting students at her alma mater, John Molson School of Business.
“Mentorship has been crucial in my career,” she says. “Different mentors have guided me through various chapters of my life, helping me navigate challenges and make pivotal decisions.”
Martini also instills this value in her children, encouraging them to volunteer and raise their hands for opportunities.
To young professionals uncertain about their career paths, Martini offers straightforward advice: “Choose an industry that excites you. Work for a company that aligns with your passions.”
As a leader, she continues to grow by consuming books and podcasts. (Good to Great remains a favorite.) But her guiding principle is simple: “Leadership is about creating success for others. When your team thrives, so does the business.”
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