You don’t usually expect to find an opera singer, a PhD, and an English major-turned-social-media exec swapping career stories in the same Zoom room. But that’s exactly what happened when Jodie Fiorenza, Menaka Sankaralingam, and Zandy Ring sat down to talk about how they got to where they are today during our Empower Her summit.
Their journeys aren’t typical. Jodie went from promoting artists at a record label to leading agency partnerships at Automattic’s enterprise arm, VIP. Menaka started in government research in India, earned a doctorate in natural language processing, and now wrangles code and data for WooCommerce. Zandy’s background in visual art and English didn’t scream “COO of Tumblr,” but here she is, running day-to-day operations at one of the internet’s original social media platforms.
What they have in common isn’t their resumes. It’s that none of them followed a map. They followed their curiosity, their instincts, and sometimes, the weird and winding roads life put in front of them.
Below, we’ll look at the surprising twists that shaped their paths, the challenges they faced along the way, and the advice they’d give to anyone navigating a career — especially when the path isn’t clear.
Pivotal career turns
For Zandy, Jodie, and Menaka, some of their most defining moments came from unexpected turns.
Take Zandy. Today, she’s the COO of Tumblr, but she didn’t get there through an MBA program or a traditional leadership track. She studied visual art. Then English. Her mom suggested a business class. She said no thanks. After a stint in marketing at an oil and gas company (yes, really), she joined Automattic as a Happiness Engineer, answering support tickets and learning the ropes.
From there, Zandy moved into team leadership, spearheaded performance and development programs, and eventually stepped into the unknown: a leadership role at Tumblr that was way outside her comfort zone.
“I had to Google what a COO even does,” Zandy admitted with a laugh. (Spoiler: She figured it out.)
Jodie’s career path is less of a ladder and more of a mixtape. She studied music and communications, worked at a record label, and got into tech when an artist friend needed a website to replace their fading MySpace page. That led her to WordPress, which led her to building sites, which led her to agency work, where she rose through the ranks in sales and strategy. When she joined Automattic, it was a full-circle moment.
“I literally went from opera to hip hop to tech,” Jodie said. “It was a very jagged road, but the best possible path I could have taken.”
Even though Menaka’s path included an actual PhD in natural language processing, it still managed to surprise her. After years in research and enterprise work, she found herself freelancing in the WordPress ecosystem. That freelance gig turned into a job at Prosperous, which was then acquired by Automattic.
Suddenly, she’d gone from a 20-person company to a global tech firm, surrounded by people from different countries and backgrounds. “It opened up a lot of opportunities in terms of the learning, the exposure, and the rotations,” Menaka said. She calls the acquisition the “most surprising turn” of her career — and the one that helped shape it most.
The throughline? They didn’t have a master plan. They tried things. And they didn’t panic when the road changed.
Lessons from the journey
None of these women got where they are by coasting, and they all picked up some hard-earned lessons along the way.
Early in Menaka’s career, she noticed her ideas weren’t always taken seriously. Not because they lacked merit, but because they came from her. A woman. Instead of letting it derail her, she stopped chasing external validation and started looking inward.
Now, when Menaka gets feedback, she gives it space. She lets time take the sting out and then decides whether it’s useful or just noise. “There are always going to be different kinds of people,” she said. “I choose to focus on the ones who respect the work.”
Jodie learned to stop treating her career like a checklist. In her twenties, she chased the milestones: job, partner, stability. But real life, of course, didn’t stick to the list. “Give yourself grace,” she said. “You’re going to make wrong choices. That’s fine. Just don’t get stuck.” For her, it’s about forward momentum, even if the direction changes. (Especially if it does.)
Zandy’s lesson? Keep learning, even when you're already juggling a busy calendar. As COO, she’s constantly adapting. She reads, listens to podcasts, subscribes to newsletters, and leans on her network.
“The more I connect with other women in leadership, the better my LinkedIn feed gets,” she joked. It’s a casual way of staying current, but also a smart one.
Unconventional advice worth stealing
Before the conversation wrapped, each woman shared one piece of advice they’ve picked up along the way:
- Menaka encourages you to “choose your own adventure.” Forget the standard route. The best opportunities often show up when you veer off the expected path.
- Zandy says, “Ask yourself: How am I being complicit in the conditions I say I don’t want?” It’s a tough question, but a powerful one. If something isn’t working, are you unintentionally helping it stay that way? Zandy’s advice is to check in with yourself and then act accordingly. Change often starts with one brave voice speaking up.
- And finally, Jodie finishes with, “I don’t believe in work-life balance.” Not because she’s anti-boundaries, but because she sees life as a whole. “Some weeks, work will win. Other weeks, family or mental health will,” she said. “It’s all life.” Instead of aiming for balance, Jodie aims for integration and gives herself the freedom to shift gears as needed.
These stories don’t come with a step-by-step guide or a tidy moral. But maybe that’s the point. Careers are built in the pivots, the pauses, and the choices that don’t always make sense at the time.
Whether you’re mid-pivot, plotting your next move, or just trying to figure out what your version of success looks like, let this be your reminder that you don’t need a perfect plan. You just need the guts to take the next step (and maybe a few good stories to remind you that you’re not alone in the chaos).
To learn more about Zandy, Menaka, and Jodie’s career journeys, listen to the full conversation, “Career Journeys — 3 Unique Perspectives,” here.
Interested in building your career with Automattic? They’re hiring! Explore Automattic’s career opportunities here
