Stilwell originally trained as an actress, playing roles in ITV1's The Bill in 1994, and onstage in London's West End theatre, as well as several commercials and voiceovers.

In order to supplement her income as an actress, Stilwell's veterinary nurse sister suggested that she start a dog walking agency.

[1] Stilwell created the Victoria Stilwell Foundation, whose mission is "to provide financial support and canine behaviour expertise to assistance dog organisations and small animal rescue shelters while promoting the concept of reward-based, positive reinforcement dog training philosophies in organisations and households throughout the United States.

She has been involved in animal welfare and protection organizations on the international stage, including serving as an Advisory Board Member of RedRover[3] and a National Ambassador for American Humane.

The show features Stilwell as she counsels families with problem pets and uses positive reinforcement training techniques to help them learn how to correct their dogs' behaviour.

Originally produced for Channel 4 in the UK, the show premiered in the US on Animal Planet in April 2007, and over 110 episodes have been aired worldwide.

Dogs With Extraordinary Jobs is a TV series, created, co-produced and narrated by Stilwell for Blue Ant Media (syndicated worldwide including the Smithsonian Channel in the US) in 2018 and 2019.

Stilwell serves on the boards of several animal-related institutions including Canine Assistants, RedRover, DogTV, Greyhound Rescue of West England, Grey Muzzle, the Soi Dog Foundation, and the W-Underdogs.

[14] After many years without a pet dog of her own (due to the international travel schedule required for her various TV shows), Stilwell adopted a rescued chocolate Labrador named Sadie.