Today’s master bucks more trends than probably anyone I’ve interviewed. She ignores the competition. She refuses to put ✨AI sparkles✨ on everything. She runs on intuition as much as data.
Yet her small, scrappy marketing team regularly punches above its weight — and wins.
When Todoist first launched, it was the original personal task manager. Today, its parent company, Doist, is still seen as the go-to in productivity software, despite competing with Fortune 500 tech brands.
Fun fact: Early in her career, Brenna moved to Chile — without knowing any Spanish — to work with Habitat for Humanity. After a chance encounter in an Irish pub, she ended up employed at the Chilean Ministry of Economy.
Claim to fame: When Todoist hit 1 billion completed tasks, it celebrated by asking users to share something important the app helped them achieve. Over 600 users shared their heartwarming stories.
Lesson 1: Make it half measurable, half memorable.
“Half your marketing should be *measurable*, half should be *memorable*,” Brenna Loury posted on LinkedIn a few months back.
And because giving people a slightly hard time is part of my job, I asked if, as CMO, she still held her team accountable to ROI for the memorable half.
“You pulled all of my hot takes, haven’t you?” Loury laughs. “I don’t think anybody on the team feels comfortable dumping money into something that’s not showing positive results. Our approach is doing small investments, seeing what works, and iterating.”
So, her quote is less about marketing with abandon, and more about not getting so lost in your KPIs that you forget you’re talking to real people. And people respond to what’s real, not what’s ideal.
“A lot of brands in the productivity space have a message of ‘Do this. Do that. Get more done.’ and it’s a very unrealistic expectation for people. We try to be really honest about what human beings can actually do."
And, in return, Doist is also honest about what its own human beings can do. Which is why lesson two is…
Lesson 2: Your faults are your forte.
Working in the productivity software space, Doist’s eight-person marketing team often finds itself the David to Goliaths like Apple, Microsoft, and Google.
But Loury says they find a competitive advantage in an unlikely place: “We’re very authentic with our users and not afraid to mention some of the shortcomings we’re working on. That’s not something that Google is ever going to do.”
It all started with some very public missteps that Loury opened up about, but it ended with a new philosophy: “Making sure that the humans that are creating Todoist are visible to the humans that are using Todoist.”
That’s why Doist’s YouTube presence is usually just an employee named Naomi who uses Loom to make videos from her living room.
And “if you look at the Todoist change log, you’ll see little face bubbles. We’ll say ‘Carrie released this update on Android’ and there’s Carrie’s little face, so that people know there are real humans working on this stuff.”
Lesson 3: The customer is always right. Sometimes.
To help prevent any more missteps, Loury’s team makes sure to keep communication open with their audience.
“We’ve been really conscientious about communicating with our users. We let them know what we’re working on and gather feedback.”
But she cautions that you absolutely can go too far in that direction. Loury laughs and points to that famous quote often attributed to Henry Ford: “If I had asked my customers what they wanted, they would have said a faster horse.”
“It has to be a balance with trusting your gut and using your intuition,” she says. “We’ve always had a strong intuition of what we wanted to build. And we always felt strongly that we wanted to build things that we ourselves would use, and in doing that, would help other people as well.”
“You can lose sight of how you want to build the product in the first place if you only listen to your customers.”
|Make Yourself a Master
A sackful of marketing shortcuts
This is how you carve out hours for dilly-dallying, vegging out, goofing off, and all fitting synonyms.
"What’s a trend everyone’s excited about that you think is overhyped or completely misunderstood?” — Maya Grossman, Executive career coach
THIS WEEK'S ANSWER
Loury says: “Adding AI chatbots everywhere. *ducks for cover*
Unless there is a very obvious use case, I feel that this is a lazy implementation of AI. Most companies need to think much harder about their users’ pain points before just slapping a chatbot onto their UI.”
NEXT WEEK'S QUESTION
Loury asks: “What is your favorite thing about marketing that can’t be easily measured?”
This week's email was brought to you by Curt del Principe. Editing by Laura M. Browning. Shout out to Leah Taylor for making the interview happen!
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