Ilyssa Caretsky

By Brad Hadfield

n a recent LinkedIn post, Ilyssa Caretsky wrote, “Who says you can’t do it all? Sometimes being a working mom means shifting gears on the spot. The playground becomes the office, calls happen with snacks in hand, and the to-do list is squeezed between swings and slides.”

While most people use the platform to present a polished version of themselves, Caretsky pushes back on the idea that everything on LinkedIn must be strictly professional, sharing anecdotes from her life—sometimes even the messy ones.

“Posts about real feelings often get the most meaningful responses,” she says. “Being vulnerable and open can help others feel seen. If something I write resonates with just one person, that’s a win.”

That instinct has also helped shape her career in branding and making customer connections. “How I approach LinkedIn is how I approach work: speak to people the way they want to be spoken to and understand their needs and pain points.”

In self-storage, a sector that outsiders often reduce to square footage, Caretsky brings the human touch, even if she found the industry by chance.

Caretsky connects for this interview from her bedroom, which doubles as an office (it’s Manhattan, after all). She’s on the Upper East Side, which boasts over 150 luxury designer shops, so it’s fitting that Caretsky spent much of her career in retail. Her resume includes Luxottica, the world’s largest eyewear company that designs brands like Ray-Ban and operates stores such as Sunglass Hut.

Her successful work in branding for the company led Caretsky into field operations, setting the stage for future opportunities. “Once you understand how stores operate, you understand how to communicate with customers,” she says. This led to high-level marketing positions at Barnes & Noble and Mattress Firm, to name a few.

But life has a way of throwing curveballs. “After my son Noah was born, I felt burned out,” Caretsky says honestly. “The economy had been tumultuous, and this industry wasn’t driving my passion anymore. I thought I’d start and end there, but it wasn’t meant to be, so I decided to hang up my retail hat and focus on Noah.”

When Noah was about six months old, Caretsky began to get the work itch again. Rather than go job hunting on professional platforms, which she figured would yield the usual results, she posted her desire to get back to work in an unusual place: Facebook’s Moms Of Manhattan group. “I don’t even really use Facebook,” Caretsky says with a laugh. “It was a spur of the moment thing, but I spelled out what I wanted, highlighted my skills, and made it clear that I needed to work remotely.”

Days later, a two-word message came through from one of the moms. “DM me,” it read.

Caretsky wrote back, and the mystery mom told her about a position with market intelligence agency Radius+. “She thought it might be a good fit for me, but of course I didn’t know anything about self-storage. But I said I’d take an interview.”

Those in her circle were skeptical. When Caretsky told her husband she’d just scheduled an interview with a self-storage data company, he raised an eyebrow. “His reaction wasn’t much different from my initial reaction,” she says. “He said, ‘Self-storage? Is that even an actual industry?’ I said, ‘I’m about to find out.’”

Caretsky was offered the job and she started a month later. She caught on quickly. “The learning curve isn’t as big as you might think, which is a testament to the people in the industry. Everyone is willing to help.”

The next evolution in Caretsky’s career brought her to self-storage data provider StorTrack, which was looking for a marketing director to oversee their brands. Along with the flagship StorTrack brand, that includes List Self Storage, an online platform for buying and selling facilities, and RV Park IQ, a market analysis and listing platform for RV parks and campgrounds. Caretsky had already met some of the players at the company and recognized that it would be a great opportunity for her to raise her personal bar while benefitting the company itself.

“I learned a lot at Radius+, but this was the right move and offered the career momentum I was looking for,” she says. “Plus, there was no animosity. People in this industry want each other to succeed, even when they’re competing. That’s what makes it so special.”

Even though both companies are data providers, Caretsky makes it clear that there are distinctions. “Each excels in a unique way,” she says. “Plus, a lot of users don’t stick to one data provider. They pull niche needs from each to make informed decisions, so it’s beneficial to the industry to have multiple players in the same space.”

Caretsky says that StorTrack’s biggest differentiator is the vast amount of historical data it houses, going back over 10 years, and the hundreds of overseas employees focused on research and development. At the helm is CEO John Tilly, for whom she has nothing but respect. “Working with John at StorTrack has been energizing. He is fair, involved, and deeply committed to the mission, and that level of leadership makes it easy to show up at my best.”

While many women have waded into the self-storage waters over the years, it’s still largely a male-dominated industry. Has this posed a challenge for Caretsky, especially as a working mom? She shakes her head. “I grew up with two younger brothers, and I love sports—I’m a long-suffering Jets fan—so being the only woman in the room has never fazed me.”

She actually had her start in professional sports, even working with those Jets. Although they were brief stints before moving to retail, they set her up for success when working with men and gave her a lot of perspective. “I can see, just in the last 20 years, how much the acceptance level for women in the workplace, and women leaders, has increased.”

In self-storage, Caretsky has never felt any sort of barriers; everyone she works with has been respectful of her role as a mother. “My team is used to my son Zoom-bombing our meetings,” she says with a laugh. “But they’re wonderful when that happens. They’ll say, ‘Hey, Noah, how was your day?’”

Caretsky adds, “I’ve been fortunate to find roles that have given me autonomy to get the job done while respecting life outside the nine-to-five.” She says that as long as she’s delivering at StorTrack, working flexible hours is not an issue. “When companies trust you, it drives you to do better work.”

When she’s not taking care of business or her son, Caretsky says she’ll continue to tell her story on LinkedIn. “I don’t do much writing at work beyond emails and content, so this has become an important outlet for that,” she says.

“It’s not always easy,” her post from the start of this story went on to say. “Some days demand more from me at work and others from me at home, but both deserve my best. What matters most is being present and intentional wherever I am. To every parent juggling work and family in real time, you’re not alone. Here’s to giving ourselves grace and finding strength in the chaos.”

These musings resonate with people, Caretsky says, and several of them have reached out to her to say thanks for making the platform a little less formal and a lot more personal. “One industry colleague messaged me to say how one of my posts helped him be more outspoken about his own struggles,” she says. “I’m not trying to be anyone’s voice, but if I can help amplify theirs, that’s an incredible honor.”