Otis D. Gibson has never met a Gertrude. Twenty-one years of running an agency by that name, and not one has walked through the door.
Gibson, founder and chief creative officer of Gertrude, took the name from Gertrude Stein — the woman the lost generation was told to go see when they landed in Paris after World War I. He spent part of his own 20s in France, and the story stuck: a name that sounds strong and nurturing at the same time, attached to a place built to enable other people’s creativity.
Since 2005, Gertrude has grown into a 55-to-65-person independent in Pilsen, working on Coca-Cola’s Red Tree division, Quaker, Diageo and Mattel. “It’s more of a concept of a thing and a person than it is an actual person,” Gibson says.
Twenty-one years in, the concept is holding.
The Gertrude he never met
People assume the name is a grandmother. It isn’t. It’s a posture.
Gertrude Stein was an advocate for the arts — the fixed point in Paris that scattered artists were pointed toward. Gibson liked the idea of building a business around that same function, and he’s spent two decades using one phrase for it: creative enabler.
The agency turned 21 on February 1. “You blink and I’m like, oh man, what happened,” Gibson says. “We’ve just kind of had a head-down approach — digging, digging, digging. You look up and 21 years later, here we are.”
What Gertrude is known for: big problems, short clocks
Gibson doesn’t oversell the sweet spot. “Just like every other agency, we’re better than some, not as good as some,” he says. Then he names the thing clients keep calling about.
Complex brand problems, solved fast.
The call usually comes from a CMO new to the seat or a CEO trying to make a big shift — reorganize the brands, move the business, change the story. “It’s generally a big thing and a big move, and it’s usually really, really fast,” Gibson says. The creative work is how that thinking gets expressed, not the thing being bought.
Three things Gertrude does well
Asked for three strengths, Gibson answers in about four seconds. Creative. Strategy and positioning. Activation.
“We know how to create big ideas that are strategically sound, and we know how to mobilize them,” he says. “Those are the three things we do very well.”
The third one is the tell. Plenty of shops can write a positioning deck — fewer can move a global portfolio into market on a CEO’s timetable. That’s where 21 years of reps show up.
Every marble conference table, every elevator ride down
Gertrude’s independence wasn’t a manifesto. It was a series of small decisions made in elevators.
Gibson and president Heather Knapp joke that they’ve sat at every large marble conference room table at every holding company over the last 20 years. “We’ve usually gotten in the elevator, looked at each other and said, ‘I think we’ll take our chances on our own.'”
The freedom is the point, and so is the ability to reshape the agency daily, weekly, hourly as the business changes. “That mentality is what’s kept us in business,” Gibson says. “We’re adaptable. We’re coachable. We see a change, we understand the rules shift, and we shift with it.”
Why brands should work with Gertrude
Gertrude’s clients can hire any agency on earth. Any agency on earth would take the call. Gibson takes some pride in the fact that they dial Pilsen instead.
Part of it is structural — the relationship sits at the C-suite, so he’s the person a CMO texts when something breaks. Part of it is temperament. “We can get excited about anything, in any subject matter,” he says of a team he cheerfully calls nerdy. “Digging deep into that brand and understanding how to write a unique strategy for them” is the part of the job they like most.
Two decades of working with multinationals also taught him something about the people on the other side of the table. The Wizard of Oz comparison is his. “The person behind the curtain is still a thing,” Gibson says. “They’re just like us. They’re trying to figure it out, and they’re looking for a real partner.”
No secret formula, no Don Draper reveal. “They’re looking for people who can be their partners, be empathetic to their business problems and help them find a clear solution.”
Never, ever, ever timesheets
When Gibson started the agency, his first move was subtraction. He listed everything he’d hated as a creative and deleted it.
Timesheets went first. They have never come back.
“Our job is to walk in the door, have big ideas, make those ideas happen and go home,” he says. New hires arriving from holding companies need a minute to believe it. One creative, laid off from a massive network and a week into the job, kept asking questions in a briefing until Gibson finally told him he’d need a few more months to adjust. “We literally see it in people’s eyes. So, never timesheets? Never, ever, never, never, ever.”
The other half of the pitch is forward motion. Gertrude is rolling out a per-employee stipend for classes and training, sparked by a senior art director deep into AI workflow — a fashion photographer who fell into advertising and never stopped being a photographer. “You don’t have to kill that part of your dream because you’re in advertising,” Gibson told him. “That can only make the work we do better.”
Misfits, maybe. Underdogs, no.
Weirdos, misfits or underdogs? Gibson takes two of the three, and he’s specific about which one he’s rejecting.
“I don’t want to be called an underdog because I’m like — what do you mean? We have a shot,” he says. “I’ve been around long enough to know we have a shot.”
The old line that bigger agencies have more people, not better ones, has stopped needing to be said. Clients figured it out.
He’s less patient with “small.” Years ago, over drinks at an award show, a global CCO friend told him it must be cool running his small agency.
“Maybe we’re not small. Maybe you’re too big,” Gibson shot back. “In no universe do I look at a group of 60 people and go, that’s a small group. That’s a crowd.”
The right-size argument is the whole business, and the math took a while. “I didn’t leave large agencies to build another large agency. That was never the dream,” he says. “The dream was to build the right size agency for the kind of work we want to do. It took 21 years, but here we are.”
Shout-out: the two people who opened the door
Gibson names two, and the second one is the better story.
First is Dan White, formerly of Coca-Cola, who brought Gertrude into the Red Tree business and bet on the agency early. “He’s an incredible leader and one of the people who really believed in us.”
Second is Peter Isaiah, the former head of procurement at Diageo — not the department that usually gets the thank-you speech. Fifteen-odd years ago, Gibson and Knapp flew to New York for a scheduled 15-minute elevator pitch. They stayed four hours, talking about cooking and everything else, and Isaiah walked out with a short list of brands he thought Gertrude would fit.
That matchmaking turned into a client relationship that ran more than 10 years. Isaiah has since retired. Gibson still calls him every few months.
“He was one of the first ones to see exactly who we were.”
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