Best Dog Training In Winter Garden, FL

Meet Matt, the proud owner of this Sit Means Sit franchise, established in 2011.

Matt began training dogs in 2009. He started alongside his mother-in-law, Jori Pollard, who owns multiple Sit Means Sit locations. From there, he built his own path and opened this franchise in 2011. Since then, he has helped grow it into a strong and respected training facility.

People often ask Matt how he got into dog training. He likes to joke, “I couldn’t pass a math class in college.” However, his passion for working with dogs and helping people quickly became clear. What started as an opportunity turned into a lifelong career.

From the beginning, Matt’s goal has been simple. He wants to create a place where people can learn how to do more with their pets. He believes training should build freedom, confidence, and real-life results. Above all, he values time. One of his favorite quotes is, “Time is the most precious commodity that is out there. It’s the one thing that you can’t buy or ever buy back.”

In addition, Matt works hard to develop his team. He pushes them to grow as trainers and as people. He believes strong leadership creates strong results. Because of this, he invests in their skills, character, and confidence.

Matt remains deeply passionate about helping others. He supports both clients and team members with the same level of care and commitment. Through steady leadership and clear vision, he continues building a company that changes lives one dog and one family at a time.

Meet Jillian, one of our head trainers and a strong leader on our team.

Jillian joined the Sit Means Sit family in 2020. Since then, she has helped many dogs and families build better communication and stronger relationships. She serves as one of our lead trainers and oversees our Ocoee location most days. Because of her steady leadership, the team stays focused, organized, and consistent.

Jillian takes pride in setting clear standards for both dogs and owners. She believes strong leadership creates confident dogs. For that reason, she focuses on structure, follow-through, and real-life obedience. She helps families understand how to lead at home. She teaches them how to stay consistent. As a result, clients feel more in control and more connected to their dogs.

She is known around the facility as our resident “Golden Girl.” Jillian owns two Golden Retrievers, Olaf and Harley. They love coming to work with her each day. They often help demonstrate proper behavior and reliable obedience. Through them, clients can see what training looks like when leadership and fun work together.

In addition to working directly with clients, Jillian supports and guides other trainers. She leads by example. She steps in when needed. She helps maintain a strong and positive training environment at our Ocoee location. Because of her experience, both clients and team members trust her guidance.

Outside of work, Jillian enjoys relaxing movie days and visiting theme parks. However, her favorite moments are spent adventuring with Olaf and Harley. Whether at the park, on a walk, or exploring somewhere new, she continues strengthening the bond she values so much.

Overall, Jillian brings leadership, experience, and heart to everything she does. She remains committed to helping dogs grow, owners gain confidence, and families build lasting success together.

Meet Deanna, one of the dedicated and driven trainers on our team.

Deanna joined the Sit Means Sit family in 2022 and has been committed to helping dogs and families succeed ever since. She has always had a passion for helping dogs become the best versions of themselves. More importantly, she enjoys playing an active role in strengthening the bond between dogs and their families.

Over the years, Deanna has developed a strong interest in working with reactive and aggressive dogs. She understands that these cases require patience, structure, and clear leadership. With this in mind, she takes a hands-on approach to behavior change. She works through triggers, builds control, and strengthens reliability in everyday situations. Meanwhile, she guides owners step by step so they can maintain results long term.

Deanna brings consistency and accountability into every session. She sets clear expectations and follows through. As a result, dogs gain stability while owners gain confidence. Her goal is always long-term success, not short-term change.

Outside of the facility, Deanna continues her passion for training with her two dogs, Amber and Cowboy. They often come to work with her and stay active throughout the day. When she’s not at work, she loads them up for beach trips or days out on the boat. These adventures allow her to continue building strong relationships with her dogs while practicing real-world obedience.

No matter the challenge, Deanna steps in ready to help dogs learn, grow, and succeed. She remains committed to guiding both dogs and owners toward lasting progress and stronger partnerships.

Meet Relena, one of our dedicated private lesson trainers.

Relena joined our team in 2024. Since then, she has helped many dogs and families build clear communication and steady progress. She works closely with clients in private lessons while also training dogs on the floor. Because of this, she understands both sides of the training process.

Relena brings a warm and kind approach to every session. At the same time, she keeps her training clean and precise. She sets clear expectations. She follows through with consistency. As a result, dogs respond well, and owners feel confident practicing at home.

In addition, Relena takes time to explain each step. She makes sure clients understand not just what to do, but why it works. This helps families stay consistent long after lessons end.

Outside of work, Relena stays active with her two dogs, Patch and Golda. Together, they compete in barn hunt and Fast CAT. They also enjoy hiking the trails of Florida. Through sport and adventure, she continues strengthening her skills and her bond with her dogs.

Overall, Relena brings patience, clarity, and steady leadership to every dog she works with. She remains committed to helping both dogs and owners grow together.