How we transformed pet care
into real care

Sit Pretty was built on a simple belief: pet care should support both the animal and the person who loves them.

I have been passionate about animals since I was six years old, but it was my professional experience in the pet care industry that ultimately shaped what Sit Pretty would become. While working as a veterinary assistant and fostering hospice cats, I witnessed firsthand the emotional and financial strain that can come with caring for a sick, aging, or special needs pet. Too often, the people who needed the most support were the ones facing the highest costs, and that disconnect stayed with me.

Later, while working as a certified dog trainer at a well-known company in Connecticut, I began to notice another pattern: many pet owners were not being given the knowledge or tools they needed to succeed long-term. Training sessions would end, but clarity and confidence did not always follow. Instead of feeling empowered, many clients were left feeling dependent, uncertain, and overwhelmed.

That did not sit right with me.

I believe pet care services should not create confusion or reliance—they should create understanding, confidence, and independence.

I started Sit Pretty to do exactly that. From the beginning, my goal has been to offer transparent, personalized, and compassionate care without hidden methods, inflated pricing, or a one-size-fits-all approach. I do not charge extra for pets with behavioral or medical needs, and I do not believe in gatekeeping when it comes to training. My clients are given the tools, education, and support they need to feel confident long after a session ends.

Today, Sit Pretty provides dog walking, pet sitting, and training services across Westchester and Fairfield counties, with a focus on reliability, communication, and real-life practicality. Every service is designed not just to care for pets, but to make life easier for the people who love them.

Because at its core, Sit Pretty is not just about animals—it is about providing peace of mind, building trust, and offering meaningful support when it matters most.

-Olivia Connolly