The Shepherd Group

The Shepherd Group As one of Toronto’s leading insurance brokerages, The Shepherd Group is in the business of protecting our clients’ futures today.

We are a trusted insurance partner, with a special focus on the needs of small businesses and entrepreneurs. The Shepherd Group is an insurance brokerage specializing in the unique needs of entrepreneurs and small business owners. We recognized that there were insurance needs for the entrepreneur, small business owner and startup companies that other brokers were not providing the right resources

or products for. That’s where The Shepherd Group is different. We look at insurance through the filter of an entrepreneur. Today, our services fill the gap where other insurance brokers fail to meet the needs of entrepreneurs. Our thinking is based around protecting your future, today.

03/25/2026

Landscapers who want a successful season, this is for you! 👀

Don’t make these mistakes, and make sure you’re fully protected.

We can help you with that 🤝🏻 Dm us today.

11/07/2025

They say tipping culture has gotten out of hand these days 😜

06/30/2025

Insurance isn’t one-size-fits-all—and it shouldn’t be.

Working with a trusted advisor means getting coverage that actually protects you when it counts, not a cookie-cutter policy full of gaps.

Let us help you get it right from the start.

Let's talk. 📲 1 866-565-6955

As proud supporters of Landscape Ontario, we’re here to help landscapers thrive 🌱From seasonal shifts to job site risks,...
06/26/2025

As proud supporters of Landscape Ontario, we’re here to help landscapers thrive 🌱

From seasonal shifts to job site risks, we understand the challenges and opportunities in your world—and we build insurance solutions that match.

✅ Tailored coverage
✅ Straightforward advice
✅ No overpaying for what you don’t need

Focus on building beautiful spaces—we’ve got the rest covered.

Big thanks to Marnie for this kind shoutout to Noah! 🙌She came to us with questions—and left with clarity, confidence, a...
06/23/2025

Big thanks to Marnie for this kind shoutout to Noah! 🙌

She came to us with questions—and left with clarity, confidence, and coverage that fits.

Looking for a broker who actually listens? You’ll want to connect with one of our team members at TSG!

📲+1 866-565-6955

Life moves fast—your coverage should keep up. Milestones aren’t just exciting—they’re also signs it’s time to review you...
06/19/2025

Life moves fast—your coverage should keep up.

Milestones aren’t just exciting—they’re also signs it’s time to review your insurance.

Let’s make sure your policy still fits your life.

📞 Talk to our team today for a quick, no-pressure coverage check. +1 866-565-6955

Cottage season is here—are you covered? 🏡🌲Before you settle into lake life, make sure your seasonal insurance is ready t...
06/17/2025

Cottage season is here—are you covered? 🏡🌲

Before you settle into lake life, make sure your seasonal insurance is ready to handle whatever summer throws your way.

Here’s your quick spring checklist to keep things stress-free:

✅ Review your seasonal property coverage
✅ Check for winter damage
✅ Inspect plumbing, water & electrical systems
✅ Confirm coverage for boats, ATVs & new gear
✅ Add liability protection if you're hosting guests

Enjoy peace of mind at the cottage—we’ll handle the coverage.

📲 Connect with our team at TSG today: +1 866-565-6955

Karim’s experience with Jessica is exactly what we strive for—professional, responsive, and personalized support from st...
06/16/2025

Karim’s experience with Jessica is exactly what we strive for—professional, responsive, and personalized support from start to finish.

Looking for insurance made simple? The Shepherd Group team is ready to help.

📧: [email protected]

06/13/2025

From business protection to future growth—we bring peace of mind through custom insurance solutions that actually fit.

Because when you're covered properly, everything feels better. 💼✨

06/12/2025

Think contractors don’t need insurance? Think again. 🛠️

From liability to equipment coverage, there are plenty of myths that leave contractors unprotected. Let’s set the record straight—your work deserves a tailored policy built for your trade.

Ready to bust the myths? Let’s talk. 📲 1 866-565-6955

The Shepherd Group has donated holiday stockings to the youth at the ❤️We know that a small thing can make a big differ...
12/16/2022

The Shepherd Group has donated holiday stockings to the youth at the ❤️

We know that a small thing can make a big difference, and we love contributing to protecting the futures of our youth.

We will continue to ensure that we are "Protecting Futures Today" and continue working with ROC.

Wishing all of your youths a wonderful holiday season.

Address

20 Great Gulf Drive
Vaughan, ON
L4K5W1

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+18665656955

Website

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