Orbit30 is a regular series where I look back at thirty years in the design industry—sharing the stories, surprises, and lessons that shaped my career. Some are small and funny, others are turning points. All of them are orbiting in my creative universe.
The Story
In 1999, the offices of Comark Inc. across the road from the Oakville GO Station weren’t exactly Madison Avenue. We were a scrappy in-house design team handling in-store signage and marketing for Cleo, a Canadian women’s fashion retailer with about 100 stores nationwide. Our desks were piled with colour swatches, floppy disks, and the faint smell of toner drifting in from the print room just steps away — a space that doubled as production hub and unofficial gathering spot. I spent countless hours in there reviewing and colour-correcting photos coming off the printers and learning the quirks of digital versus offset print. It wasn’t glamorous, but it grounded me in every detail of how Cleo’s signage came to life — an insider edge no distant agency could match. Big campaigns? Elaborate window takeovers? Those were shipped in from the outside, courtesy of high-profile New York firms with price tags to match.
That spring, Cleo unveiled a rebrand that practically screamed “millennium chic.” Gone was the stodgy serif logo in black-and-white. In its place: lowercase “cleo” in a stretched, clean typeface, paired with a warm butterscotch hue and supporting tones of creams, rusts and brown. Sophisticated. Modern. The kind of thing you expected to see in SoHo, not suburban malls.
The masterminds? Desgrippes Gobé—one of the hottest names in branding at the time. Their files arrived with that signature curved-earth and star logo stamped on everything, like a seal from Olympus. We all thought the same thing: they must have paid an absolute fortune for this.
And yet… when we saw their first in-store campaign templates, the mood shifted. The design was sleek, yes, but the Helvetica Neue Thin typeface was hard to read, potentially alienating when you imagine Cleo stores in places like Moose Jaw and Red Deer. Liesa, my manager, and I exchanged looks. Were these beautiful ideas actually going to connect with Cleo’s customers?
Then came the meeting that changed everything. Someone mentioned Cleo’s upcoming window campaigns. Liesa and I seized the opening:
“Could we… take a crack at that?”
The execs hesitated. This was Desgrippes Gobé territory. But then came the kicker: our work wouldn’t just be in-house—it would be cheaper. Andre Brenninkmeyer, Cleo’s GM and a member of the family that owned Comark, gave us the nod. “Okay. Show us what you’ve got for Fall–Holiday ‘99.”
And just like that, we were in.
Building the Campaign
For weeks, I embedded myself with Cindy McCleery, head of visual merchandising. I attended internal “fashion shows” to see the seasonal lines. I touched fabrics, studied colourways, and learned which pieces would land in stores week by week. The level of access was intoxicating. Unlike an external agency, I wasn’t designing in a vacuum. I lived the business. I immediately realized the in-house advantage in this space: elevator rides with buyers, cafeteria chats with merchandisers, even passing conversations with Andre where he’d drop sharp little lessons about retail and design — reminders that the best designers don’t just create, they sell. Those daily elevator rides and cafeteria chats weren’t small talk — they were intelligence. Insights you only pick up by living the business, not parachuting in from outside.
Then came the fun part: sketching, writing, building campaigns.
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August Launch: Olive greens, oranges, suede-like blazers. I proposed a leafy, abstract backdrop with the line “Fall Feels Fantastic.” Corny? Maybe. But it balanced emotion with fabric texture, and the merchandising team loved it.
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Mid-Season Sale: Branded colour-blocking in seasonal tones, not bargain-bin red and yellow. A sale campaign that actually looked sophisticated.
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Holiday: No posters. Just glittery holiday party wear brought forward as the focus, stars and sparkles on the glass, and the words “Light up the season” in vinyl. Minimal, modern, daring.
And then there was the third wave.
The Turtleneck Moment
September was all about ribbed turtlenecks in every colour imaginable. My idea? Line up mannequins, each wearing a different colour, and anchor it with a stark white poster showing nothing but the cropped, top-down view of a turtle. The headline:
“The turtleneck… Going fast.”
It was absurd. Bold. Maybe even a little off-brand. But it made me laugh, and more importantly—it made the point.
When presentation day came, I laid everything out for the Cleo senior leadership team. Andre sat at the head of the table. No slide deck, but actual real size mockups of the windows themselves, campaign by campaign, in a massive boardroom. I walked them through the season’s flow. I even built cost tiers—high-impact and low-impact versions—so stores of different sizes could adapt.
And then the turtle appeared.
Andre’s jaw literally dropped. He leaned forward. He couldn’t stop smiling. He admitted later he wasn’t sure if it was on-brand, but he didn’t care. He loved it. He wanted it in stores.
The room shifted. Desgrippes Gobé was out. We were in.
Aftermath
Within days, we were rolling out my campaigns to 100 stores nationwide. A few months later, I was promoted to Cleo’s Principal Designer. My new office was a dream: massive desk, private meeting table, excessive collaboration and brainstorming space, racks of clothes nearby, and a creative energy that was unlike any space I’ve had since.
From there, things snowballed. Cleo hired a marketing lead, Linda Hannigan, and together we took over not just the campaigns but the photo shoots. We defined “the Cleo model,” flew to Vancouver for weeklong shoots, and storyboarded integrated campaigns that stretched from window displays to brochures to chic mini-lookbooks. We even designed perforated “share-with-a-friend” offers—classy little booklets that doubled as fashion guides and referral drivers. Suddenly, we weren’t just designing ads—we were building a customer loyalty engine.
I even became the unofficial guardian of Cleo’s new butterscotch brand colour. We developed a custom ink because no Pantone formula matched it exactly. Every fabric, print job, and embroidery came across my desk for approval. The kid who once designed flyers, newsletters and cut business cards in the adjacent print shop was now the keeper of the brand. Approving every swatch and print run made me realize: owning the tiny details is how you build brand trust. That kind of vigilance is hard to outsource.
At the end of 2001, I moved on—new house, higher paycheck, different priorities. But that moment in 1999, standing in front of Andre and selling him on a turtle, sealed my reputation at Comark forever.
Lessons
Looking back, I see three lessons I carry to this day:
- Courage pays off. We didn’t wait to be asked. We asked. And then we swung big.
- Goodwill compounds. That one bold pitch bought me years of trust and credibility with leadership.
- In-house can beat the big guys. We knew the fabrics, the store layouts, the merchandising quirks. We lived the business. That insider edge was something no detached agency could replicate.
The irony? Beating Desgrippes Gobé didn’t just teach me about design. It taught me about leadership, trust, and the value of being close to the work. Lessons I’ve carried into every role since.
Orbit30 is my way of connecting the dots between past and present—moments from my career that continue to shape how I think about design and creativity today. Here’s to the turtle that proved sometimes the boldest move is also the simplest.
