The CEO Has Separation Anxiety

This is the story of how one woman built a pet care company by solving her own problem first and testing it on her dog for a year. And the CEO isn’t who you think it is.

Kelly came into Rubina Singh's life in August 2020, right at the peak of the first lockdown. He was three and a half years old, had changed a few homes, and arrived with enough separation anxiety to ruin a room if left alone for five minutes.

She thought she'd foster him.

We all know how that goes.

The problem was personal. And then it bit back. Literally.

Rubina was at the peak of a corporate career when Kelly joined her. She traveled a lot for work. She tried boardings. She tried home boardings. She tried part-time sitters. Every time, Kelly came back sick, or stressed, or carrying someone else's problems on him. Sometimes literally. The turning point came during one trip. She picked Kelly up from a home boarding and found a bite on his snout. "That was it," she said. "Enough. I have to figure this out myself."

What followed wasn't a leap. It was a test.

The first pilot had four legs and a name.

Rubina didn't quit her job when the idea came to her. She didn't quit when she knew it was good. She didn't quit until she'd spent a year proving it.

She hired a sitter for Kelly, put them on salary, and ran a quiet, private version of Kelly and Crew while still working full time. His personal crew, of course! Every time she traveled, something was being tested: the update rhythm, the routine-following, the medication, the grooming. What worked stayed. What didn't was noted. After a year of that, when she saw that this was something that could work, because she just saw it happen, she quit.

Then she spent six months studying canine cognition at Duke University while simultaneously building the company's framework. "I'm a little by the book," she said. "I wanted to show that this is not whimsical. It’s not just love and empathy which is paramount. But it’s backed by science and education.”

Rubina calls it being careful. The distinction is probably why Kelly and Crew works.

A house of sitters who share a kitchen.

At the core, Kelly and Crew is a pet sitting service. But it is also so much more than “just” a pet sitting service. A sitter comes into your home and takes care of your pet in your absence: the routine, the food, the medication, the walks, the moments when the pet refuses to eat because you're not there, and the sitter has to figure out that hiding a treat in the bowl is plan B.

The part that's unusual is that every sitter is a full-time employee. Not a gig worker. Not a college student who cancels the morning of your flight. Full-time, trained, salaried. And this detail matters: they all live together. Same team, same culture, same food, same language.

"Pet sitting is a full-time job," Rubina said. "If pet parenting is full-time, then pet sitting, where you're shadowing the pet parent entirely, is full-time too."

She'd spent years watching the alternative. Apps where anyone could sign up. Sitters who didn't show. Pet parents canceling trips because there was no backup. The problem wasn't the concept of pet sitting. The problem was that nobody had organized it like they meant it.

Meet the nine-and-a-half-year-old CEO.

When we asked Rubina who the real client was, the pet parent or the pet, she didn't hesitate. "The pets are the bosses. In our systems, it's their name that comes first." She meant it literally. When a booking is created at Kelly and Crew, the pet leads. The pet parent follows. They also collect nicknames. Because nobody actually calls their dog by its real name, every sitter is briefed on the full range of terms of endearment before they walk through the door. The embarrassing ones. The ones that don't translate. All of it. So the pet hears something familiar from someone new. Make way for “donkey”, “bholu”, “chotu”, “dude”, “babu”, “bushu”.

Sitters at Kelly and Crew change their uniform between every sitting of the day. Because dogs and cats are sensitive to the smell of other animals. Because a pet meeting a sitter who smells like three other pets is a pet who's immediately unsettled. Because that detail, invisible to every pet parent who will never know it happened, is the difference between an animal who's at ease and one who isn't.

Nobody mandated this from outside. It was built in. That, in the end, is the whole argument: that it's possible to build a company careful enough to think about what a dog might smell on a stranger's sleeve, and disciplined enough to actually do something about it. Every time. Without being asked. The pets are the bosses. They just don't know how well-run the place is.

The number that doesn't need ads.

Kelly and Crew has never run an ad. Every booking has come through word of mouth. Their retention rate is 100%. Rubina said it quietly. Then said it again when we asked her to confirm. One hundred percent. Every pet parent who has booked has rebooked. "I say that with a lot of pride and a lot of gratitude for the team."

The team, by the way, is also why Rubina can no longer travel easily. Kelly, the original Kelly, the dog this whole company is named after, does not have a sitter. The team is always booked out.

The CEO, nine-and-a-half years old, is managing just fine.

Scale is easy. Not becoming 'massy' is the hard part.

Rubina is expanding to other cities. But she was clear about what she's protecting in the process.

"We want to keep it compact. The care, the standards, the attention. That cannot fall." She used a word we've been thinking about since: massy. What happens to most things that scale? The energy disperses. The personal becomes procedural. The warmth moves from something that happens to something that lives on a website.

The evidence that it hasn't happened yet: pet parents bring back gifts for sitters when they travel. Menus are laid out for sitters during long stays. A dog with partial paralysis, whose parents had never once been able to travel before, got to see her owners go on holiday, and came back exactly as she'd been left. "We got so many blessings from them," Rubina said. “That is the validation that the work we’re doing at Kelly & Crew is worth it.”