Best Business Insurance Options in Winnipeg
We extensively test and research all services we review. Here's why you can trust us.

Reviewing the Best Business Insurance Options in Winnipeg

Business can sometimes be messy. That’s why investing in proper business insurance has always had more palpable gains than losses – it’s a nice hedge against those occasions when things go wrong.

Anyway, we went looking for the top business insurance providers in Winnipeg (as well as the top brokers, if that’s what you’re interested in). Before we get to the list, let’s cover the basics such as the cost and how much each type of insurance can cover.

How much does business insurance cost and cover in Winnipeg?

It is important to understand the different types of business insurance before choosing one. Along with this, you will need to get a good grasp on your business’ needs first given your roadmap.

Below is a table of ranges of median monthly costs of the most common and other types of business insurance.

Type of InsuranceMedian Monthly Cost
General Liability Insurance (Commercial General Liability)$425 to $921

Of course, these would depend on the particular need and the scale of coverage needed.

And speaking of coverage, here is how much each type of business insurance would cover along with other things you may need (includes the costs of legal expenses, monetary judgment, settlement fees, etc.).

Type of InsuranceCoverage (includes replacement of damaged properties, legal expenses, monetary judgment, defence costs, etc.)
General Liability InsuranceFrom $10,000 to $25,000
Professional Liability InsuranceFrom $56,000 to $250,000
Errors and Omissions InsuranceFrom $33,000 to $250,000
Directors and Officers Liability InsuranceFrom $120,000 to $639,000
Commercial Property InsuranceFrom $7,500 to $87,000
Business Interruption InsuranceFrom $18,000 to $55,000
Builder’s Risk InsuranceFrom $88,000 to $375,000
Cyber Liability InsuranceFrom $455,000 to $500,000
Builder’s Risk InsuranceFrom $88,000 to $375,000
Legal Expense InsuranceFrom $10,000 to $20,000
Malpractice InsuranceFrom $47,000 to $102,000
Liability InsuranceFrom $11,000 to $45,000
Product Liability InsuranceFrom $85,000 to $330,000

The most commonly chosen ones, by the way, are usually general liability insurance, errors and omission insurance, and commercial property insurance.

The Best Business Insurance in Winnipeg

We had to check out quite a few business insurers to put together this list. Anyway, here are the best business insurance providers in Winnipeg right now, at least based on what we’ve seen and our survey.

1. TruShield Insurance

TruShield Insurance
PRODUCTSHome-based Business Insurance
Professional Services
Retail Small Business Insurance
Contractors Insurance
Commercial Auto Insurance
Group Benefits
ADDRESS105 Adelaide St. West
Toronto, ONM5H 1P9
CONTACT DETAILSPhone: 1-844-429-9480
OPERATING HOURSWeekdays only, 8:30AM to 5:00PM 

TruShield Insurance claims to be the first direct-to-consumer small business insurance provider in Canada. Obviously, that means they mainly cater to small business owners.

Don’t be fooled into thinking that means they’re small fry, though. Their insurance policies are rated positively even by  global credit rating agencies: A (excellent) by A.M. Best, A- (strong) by S&P, and A (good) by DBRS Morningstar.

If you’re a beginner, this may be the perfect choice for you. Their offerings are as simple as it gets and are really affordable. Their offered programs start at $42 a month.

Of course, the downside of TruShield Insurance lies in their intended market. If you’re a business owner who’s looking to scale up anytime in the future, their policies may not suit your needs and may not be able to cover the scope and complexity you wish to aim for in the long run.

To add, some of the policyholders we talked to have also highlighted some issues in how fast they tend to their customers. Others didn’t have the same problem, but whenever anyone complains about this, it’s worth mentioning.


  • First direct-to-consumer small business insurance provider in Canada
  • Highly rated by global credit rating agencies
  • Simple and affordable insurance programs starting at $42 a month


  • Suitable only for small businesses
  • Some noted issues with customer service

Customer Reviews

Great customer service and reasonable prices – Tory Dunn

“The customer service is phenomenal, their prices are super reasonable and my insurance was ready to go minutes after completing the application. Highly recommend TruShield for all of your insurance needs!”

Easy transaction, but slight issues with scheduling

“Very helpful and easy to work with.  Very busy though.”

2. Federated Insurance 

Federated Insurance
PRODUCTSCyber Risk Insurance
Commercial General Liability Insurance
Commercial Property Insurance
Commercial Auto Insurance
Business Interruption Insurance
Comprehensive Crime Coverage
ADDRESS255 Commerce Drive
Winnipeg, MBR3C 3C9
CONTACT DETAILSPhone: 1-844-628-6800
FAX: 204-783-4443
Email: [email protected] 
OPERATING HOURSMondays to Thursdays, 8:00AM to 4:00PM

Federated Insurance is a business insurance company that has been around since 1920. If you’re one to look at track records, theirs is plenty rich with experiences with locals.

Given their long history in the field, the company has managed to develop and expand their range of business coverage options as listed above. This roster of products are supposed to reflect the current needs of the Canadian economy.

We like that the company provides you with a step-by-step process for you to not get lost along the way. Once onboard, they immediately put you in contact with a Commercial Insurance Specialist for them to consult your business and understand which will be the best option for you.

It is highly rated by customers. One of the major things we like is that there are flexible payment options to choose from.

Our only complaint is probably that the information on their website seems to be lacking if you’re one who wants to get as much information on their services ASAP. There are no FAQs available for people canvassing their options, for example, and you will have to reach out to them for further queries or clarifications.

That aside, they’re pretty solid, in our opinion. They’re easy enough to reach, offer some attractive policies, and have been reported fairly reliable by policyholders.


  • Has been in the field for over 100 years
  • Offers an expanded range of business coverage options
  • Strong financial stability
  • Professional assistance online
  • Flexible payment options
  • Free and instant quote


  • Official website lacks a bit of information
  • No FAQs available for customers

Customer Reviews

Fast and accommodating process – Kendra Daniel

“As business owners, we have enough stress on a daily basis of running the company. To be honest, I was in complete awe you were so fast and accommodating in getting this all rectified for us. We are super busy on a daily basis, and I always felt that we were in good hands with you.”

Detailed, diligent, and transparent – Gregory P. Nakonechny

“Federated Insurance has been detailed, diligent and transparent with a view to ensuring appropriate cost-effective coverage for your business. On the claims side, responsive and accessible best describes their service. With Federated Insurance, we don’t just have an insurer; we have a real partner in our risk management program.”

3. Aviva Insurance Company of Canada

Aviva Insurance Company of Canada
PRODUCTSAviva Enterprise Insurance
Global Corporate & Specialty Solutions
Risk Management Services
ADDRESS10 Aviva Way, Suite 100
Markham, ONL6G 0G1
CONTACT DETAILSPhone:  1‑800‑387‑4518
OPERATING HOURSNot listed online

No matter what size you are right now or what size you aim for in the future, Aviva Insurance Company of Canada has options for you. It has Aviva Enterprise insurance for small to medium-sized enterprises and Global Corporate & Specialty solutions for large corporate or commercial businesses.

One thing we really like about Aviva is that its flexible and customizable insurance programs can be recalibrated to fit your evolving needs. It recognizes that businesses aren’t meant to stay put – which means business insurance needs to account for that evolution.

They are also rated AA- (very strong) by Standard and Poor’s and A by A.M. Best. This tells you they’re a pretty solid insurer.

On the other hand, however promising their offerings sound and the high global ratings, the lack of customer reviews online may posit some doubts as to how they are on the grassroots level. 

We did talk to some policyholders and they seemed generally satisfied, though. A few also noted that Aviva’s rates sometimes fall on the higher end of the scale as well, but it’s probably best to get a quote first, given their highly customized offerings.


  • Can cater to small, medium, large-sized businesses
  • Customizable and adaptable coverage


  • Can be slightly expensive
  • Hardly any customer reviews online

Still haven’t decided? Don’t worry. Along with our list of insurers, we’ve also reviewed the top insurance brokerage firms that you can approach for your business insurance needs.

The Top Business Insurance Brokers in Winnipeg

Now, we know that a lot of people today prefer to have others sort through the many policies and policy providers for them. That’s why we also put together a list of the top brokers for business insurance here.

1. Zensurance

INSURANCE1. Commercial General Liability Insurance
2. Professional Liability Insurance
3. Errors and Omissions Insurance
4. Directors and Officers Liability Insurance
5. Commercial Property Insurance
6. Business Interruption Insurance
7. Builder’s Risk Insurance
8. Cyber Liability Insurance
9. Legal Expense Insurance
10. Malpractice Insurance
11. Liability Insurance
12. Product Liability Insurance
ADDRESS200 University Ave #1302
Toronto, ONM5H 3C6
Email: [email protected] 
OPERATING HOURSMondays to Thursdays, 9:00AM to 5:30PM
Fridays, 9:00AM to 4:00PM

Zensurance is a prominent insurance company known for its intuitive services. Partnered with over 50 leading Canadian insurance providers, the company has become widely known and trusted for effectiveness in providing insurance broker services.

For first timers and small business owners, Zensurance may give you a sense of reassurance. They are able to quickly provide information on the different types of business insurance, how they work, and even get you a free quote just with one click on their online website.

The company also provides full transparency on your purchases and coverage in clear language. This is to make sure everything is on track and no questionable things are ongoing in your deal.

We also like how the deals are very customizable according to your business. They deal with their clients in a very hands-on manner, learning all the details along the way.

If you’re running a large business, though, Zensurance may not be the right choice for you. Its focus is mainly for small to medium-sized businesses.

Since it mainly caters to small to medium-sized businesses, the complexity and scale of their programs and policies may also reflect that. If your business is one that is looking to grow or scale significantly, you might have to look at the other choices.


  • Beginner-friendly
  • Convenient and easy to use online platform
  • Full transparency of coverage
  • Curated according to your business
  • Free and instant quote
  • Contains FAQs for customers


  • Suitable only for small to medium-sized businesses
  • Might be too basic or beginner-friendly for complex businesses

Customer Reviews

Affordable rates

“Cheapest rate available and prompt service to requests.”

Highly recommended by small business owners

“I strongly recommend this company as a small business owner.”

Smooth and seamless process

“Our Agent Dave D. Made the process very smooth and seamless. We answered all the questions and received explanations of the coverages, very professional and still friendly.. Quick response from the underwriter and very reasonable premiums. I’m Johnny K Jerky and I Like Zensurance.”

2. MIG Insurance

MIG Insurance
INSURANCE 1. Business Interruption Insurance
2. Commercial Auto Insurance
3. Commercial General Liability Insurance
4. Commercial Property Insurance
5. Contract Surety Bonding
6. Cyber Insurance
7. Professional Liability Insurance
8. Directors and Officers Liability Insurance
9. Errors and Omissions Insurance
10. Product Liability Insurance
11. Risk Management Services
ADDRESS1401 Portage Avenue
Winnipeg, MBR3G 0W1
OPERATING HOURSMondays to Fridays, 9:00AM to 5:00PM
Saturdays, 10:00AM to 4:00PM

MIG Insurance started out as a family-owned business. Over time, they managed to expand across nine locations along Western Canada.

Their perspective is unique in that their priority seems to be ensuring clients’ decisions are very informed. Their tools and platform are quite user-friendly – we think they do help save you the time and energy through your purchase.

Another thing we particularly liked about MIG Insurance is that their website contains food-for-thought articles related to your purchase. These may supplement and guide you through the decision-making process easier.

These all fall under the organizational mission to provide a customer-centric experience called Buyer Friendly Insurance. This also includes providing insurance guides upfront and having professional assistance available online 24/7.

Unfortunately, we’ve seen some pretty bad employee reviews that can reflect how they’re faring in managing their business internally. We found them easy to use, as did other customers, but complaints about internal troubles are always worth noting – we just hope they can get their act together where their employees are concerned.


  • Customer-centric experience that prioritizes consumer information
  • A lot of consumer resources on their platform
  • Contains a buyer-friendly bot
  • Free and instant quote


  • Bad employee reviews

3. Pembina Insurance Services

Pembina Insurance Services
INSURANCE1. Building Owners Insurance
2. Church Insurance
3. Officer/Retail Property Insurance
4. Commercial General Liability
5. Contractors Insurance
6. Errors & Omissions Insurance
7. Convenience Store Insurance
8. Electricians Insurance
9. Florist Insurance
10. Health & Fitness Business Insurance
11. Janitorial Insurance
12. Laundromat Insurance
13. Pizza Parlour Insurance
14. Plumbing Contractors Insurance
15. Restaurant Insurance
16. Manufacturers Insurance
17. Professional Liability Insurance
ADDRESS337A Pembina Hwy Winnipeg, MB R3L 2E4
Email: [email protected] 
OPERATING HOURSWeekdays only, 9:00AM to 5:30PM

Pembina Insurance Services is known to have been providing insurance broker services within Winnipeg for over 30 years. It’s part of why they are widely known by locals.

Their process is pretty standard. They do have hands-on claims assistance, though, and will do the shopping for you once you’ve given them all the necessary information.

We like that their payment plans are convenient and they offer flexibility too. They’re able to offer discounts depending on the nature of the request.

While they offer a wide variety of insurance programs, they also pay attention to the particularities of the businesses. They have insurance programs available for very specific types of businesses such as pizza parlors or small-time restaurants.

On the other hand, the complexity and scale of the programs may still be on the basic level for now. It’s largely focused on smaller businesses, we think.


  • Claims assistance and will do the shopping for you
  • Convenient payment plans
  • Offers discount
  • Offers a wide variety of insurance on very specific types of business like pizza parlors and restaurants


  • Seems to focus on smaller or less complex businesses for its business insurance offerings

FAQs about Business Insurance

Made up your mind or still contemplating? Don’t hesitate to let us know what you think of our selections!

And if you’re also on the lookout for other forms of insurance, you can check out our article on the best insurance brokers in Winnipeg. This can definitely help if you’re canvassing your options or just deepening your knowledge on the basics of getting insurance.