Sitter loves dogs, dog gone it!

Roberta Greenspan thought of the idea of starting a dog walking and dog sitting service after she started walker her brother’s dog as a favor to him. | Jackie Pilossoph~For Sun-Times Media

Updated: January 29, 2013 8:36AM

Three years ago, when the Witkowski’s took a family vacation, they decided to leave their puppy, Remy with a dog sitter.

It was the first time the Winnetka family had ever left the Cockapoo, and they said it wasn’t easy.

“It was like dropping him off at Kindergarten,” said Ann Witkowki, it was really hard.”

Witkowksi said her decision to leave the dog with Roberta Greenspan, owner of Happy Tails To You was a great one, and that Greenspan made them feel at ease immediately.

“She just said, ‘Go’ and then she called us a couple hours later to make sure we were okay, and to tell us he was fine,” Witkowski said.

Happy Tails To You is an 8-year-old company started by Greenspan, who walks, and provides daycare and overnight boarding to dogs.

Greenspan, who had a long term career in retail before starting the business said she thought of the idea after she started walker her brother’s dog as a favor to him.

“He was going to hire a dog walker and I offered to help him,” said Greenspan, who runs her business out of her Highland Park Home, but whose clients come from all over the North Shore, “ And I’d be walking his dog and thinking, ‘This is fun and I know there’s a need for it.”

Greenspan said she was a little hesitant at first, because she views it as a huge responsibility, and she didn’t want her house getting destroyed. But she paced herself and went slowly, and now she couldn’t be more pleased with her career choice.

“It’s such a happy business,” she said, “You walk in and they love you. Being around dogs is therapeutic and soothing, and it’s nice to be outdoors walking them and playing with them.”

Greenspan, whose business is bonded and insured charges $50 per day to board a dog, and $15 per dog or $20 for two dogs for a 20-minute walk.

The dogs who stay at Happy Tails To You have the run of most of Greenspan’s house. In other words, they aren’t crated. Plus, they can enjoy her big fenced in backyard.

Clients are also welcome to call and check in on their dogs, and Greenspan often emails her clients photos while they’re away.

“For a lot of people, it’s a lot like leaving your child when you go away,” she Greenspan, who owns three dogs herself, “People are worried and they want to make sure their dog is okay.”

Lulu Witcoff, of Glencoe, has been a client of Greenspan’s for four years, and has left her Bichon Poodle, Billy there many times.

“Billy is not a dog who can go with the flow,” said Witcoff, “When he’s not at home, he gets depressed and sad and doesn’t eat.”

Witcoff said Greenspan is different than other dog sitters she’s used in the past, because she caters to his needs, often going to the extreme of giving the dog flank steak mixed into his food to get him to eat.

“Roberta genuinely loves the dog,” she said, “She’s affectionate and warm. When other dog sitters couldn’t put up with Billy, Roberta could. It’s not just a business for Roberta. She goes so above and beyond and truly caters to what the dogs need.”

“Roberta’s is such a good place for him,” said Witkowski, “She walks him, she plays with him, and he enjoys the homey environment.”

“I love all the different personalities of the dogs,” said Greenspan, “And they all make you feel loved and appreciated. I get attached to all of them and I get really sad when they leave.”

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