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Top Insurance Companies in Toronto (101)

Collectors
Consumer Web • eCommerce • Machine Learning • Software • Sports • Analytics
8 Offices
2,246 Employees
45 Benefits
Helping collectors to pursue their passion.

Collectors has multiple business lines that grade, authenticate, and sell millions of high-value, record-setting collectibles. We're the leader in third-party authentication and grading services for high-value collectibles including trading cards (Professional Sports Authenticator and Card Ladder), coins (Professional Coin Grading Services), video games (Wata), event tickets, autographs, and memorabilia, and with your help we can continue to grow rapidly. Our...

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Collectors

Collectors's Top Stability & Growth Strengths

Strong Market Position & Advantage: PSA’s grading activity scaled to well over 19 million cards in 2025 and continued rising into 2026, while the portfolio also includes SGC and an agreement to add Beckett. This combination points to a commanding position in trading-card authentication and grading.

Market Expansion: New and expanded facilities in the U.S. and internationally, coupled with portfolio additions like the planned Beckett acquisition, extend geographic and category reach. Headcount has grown into the thousands with ongoing recruiting across functions.

Investor Backing & Capital Strength: A $200 million program was announced to expand PSA’s footprint, technology, and staffing over 18 months, alongside prior financing that valued the company in the billions. These commitments indicate ample capital available to scale capacity in response to rising demand.

Wisedocs
Artificial Intelligence • Healthtech • Insurance • Software
2 Offices
40 Employees
12 Benefits
We allow medical records and other data to be processed in real time, with advanced customizable machine learning output

We want to build a future where working with medical records efficiently is the standard Our mission is to erase the headache of manual work to create a more positive experience for insurance companies, legal firms, healthcare providers, and their claimants.

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Wisedocs
Too Good To Go
Food • Social Impact
26 Offices
1,500 Employees
20 Benefits
Too Good To Go is a certified B Corp company, on a mission to inspire and empower everyone to fight food waste

At Too Good To Go, we dream of a planet with No Food Waste. We operate a win-win-win business model: For people, profit and the planet. Too Good To Go's focus is to help save good food from going to waste. By doing so, we help businesses unlock revenue from their surplus, help consumers enjoy good food at great value for...

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Too Good To Go
Manulife
Fintech • Insurance • Financial Services
26 Offices
32,427 Employees
7 Benefits Hiring Now

Manulife is a leading international financial services group that helps people make their decisions easier and lives better. With our global headquarters in Toronto, we operate as Manulife across our offices in Canada, Asia, and Europe, and primarily as John Hancock in the United States. We have more than 40,000 employees, over 116,000 agents serving ~34 million customers worldwide, and...

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Manulife

Manulife's Top Stability & Growth Strengths

Strong Revenue Growth: Analysts forecast a sharp jump in revenue over the next year and continued earnings expansion through 2026–2028, indicating strong near-term growth expectations.

Investor Backing & Capital Strength: Capital and solvency indicators are positioned as robust, including an A+ financial strength rating and a strong LICAT ratio, alongside sizable remittances and ongoing shareholder returns.

Strong Market Position & Advantage: The company is described as a category leader in Canada with top-tier positions in multiple Asian markets, supported by large AUMA/AUMA scale and a long operating history that reinforces competitive standing.

Cowan Insurance Group
6 Offices
516 Employees
14 Benefits

Cowan Insurance Group (CIG) has been providing customized, comprehensive insurance and risk management professional advice and placement to meet commercial and personal insurance, group benefits, and wealth management needs since 1927. Proudly independent and Canadian-owned, our award-winning client-centric approach and commitment to innovation and excellence have established us as a true market leader. Experience and Knowledge at Your Service Cowan Insurance Group represents...

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Cowan Insurance Group
Coalition
Insurance • Cybersecurity
8 Offices
618 Employees
21 Benefits Hiring Now

Coalition is the leading provider of cyber insurance and security, combining comprehensive insurance and proactive cybersecurity tools to help businesses manage and mitigate cyber risk. Coalition’s unique product offerings combine best-in-class insurance and proactive cybersecurity tools to help keep businesses safe.

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Coalition

Coalition's Top Stability & Growth Strengths

Market Expansion: Global reach has widened with new operations in France, Denmark, and Sweden atop existing footprints in the U.S., Canada, the U.K., Australia, and Germany. Expansion into enterprise segments via higher-limit offerings and a major partnership with Allianz supports entry into larger markets.

Innovation-Driven Growth: The Active Insurance model blends coverage with continuous security monitoring, and acquisitions like Wirespeed deepen automated threat mitigation and MDR capabilities. Scaling incident response and AI-driven security offerings signals ongoing product and technology expansion.

Investor Backing & Capital Strength: Capital foundations include roughly $800M raised, a $5B valuation, and strategic equity ties with major global insurers. Reported cash-flow positive operations and active secondary-market interest further reinforce financial capacity to scale.

Munich Re Automation Solutions
29 Offices
114 Employees

Munich Re Automation Solutions has been at the forefront of the digital revolution in insurance for over 30 years. We have a proven track record of working with forward-thinking customers to unlock new sources of revenue and greater customer satisfaction. We’ve made it our mission to continually reinvent the consumer’s experience of buying insurance. Today, we help insurers grow their businesses...

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Munich Re Automation Solutions
Optiom Inc.
Insurance
3 Offices
102 Employees

Optiom is an affordable car replacement insurance provider that helps you get back on the road when your primary insurer writes off your vehicle. Adding Optiom car replacement insurance is quick and easy; simply find or visit your broker now. Visit our website at Optiom.com to learn more about how we can help you today. Turbocharge your car insurance with Optiom.

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Optiom Inc.
Northbridge Financial
Insurance • Financial Services
2 Offices
1,863 Employees
16 Benefits Hiring Now

Northbridge Financial Corporation (NBFC) is a leading commercial property and casualty insurance group that has helped protect Canadian businesses for 100 years. We offer a wide range of innovative solutions through our Northbridge Insurance, TruShield Insurance, and Federated Insurance brands. We’re passionate about protection, prevention and progress – for our customers, and in our communities. Our exceptional service and extensive...

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Northbridge Financial
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Fairfax Financial Holdings Limited
Insurance • Financial Services
2 Offices
710 Employees

Fairfax Financial Holdings Limited is a Canadian diversified financial holding company headquartered in Toronto, Ontario. Through subsidiaries, it provides property and casualty insurance and reinsurance, alongside investment management services. Its operations span Canada, the United States, the Middle East, Asia, and other international markets, making insurance and related financial services the core of its multinational business and principal operating focus.

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Fairfax Financial Holdings Limited
Gore Mutual Insurance
Fintech • Insurance • Payments • Financial Services
3 Offices
617 Employees
14 Benefits Hiring Now

Built on a foundation of financial strength for more than 180 years, Gore Mutual Insurance Company is one of Canada’s first property and casualty insurers. With offices in Cambridge, Toronto and Vancouver, Gore Mutual is a Canadian mutual company offering competitive insurance products through trusted broker partners. Every decision and investment made is anchored in the long-term benefits to customers,...

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Gore Mutual Insurance
SecondShop
Retail • Appliances
Burlington
34 Employees
They’ll think you paid full price! SecondShop.ca

At SecondShop we are redefining how you shop – saving you money while making a real impact on the planet. Why We Started Every year, perfectly good products end up in landfills or gather dust in warehouses. We knew there had to be a better way. That’s why we set out to create an innovative marketplace that gives these products a second...

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SecondShop
Perigon Life
Insurance
Toronto
Revolutionizing the voluntary benefits industry in Canada by offering simple, easy and cost-effective products.

Perigon is Canada’s leading voluntary benefits technology platform, offering simple, cost-effective, and portable insurance solutions through a seamless digital experience. Founded in 2021 by a group of Canadian insurance industry leaders, Perigon was created to simplify the sourcing, purchasing, and management of voluntary benefits for employees, association members, and organizational stakeholders. With the belief that voluntary benefits are a vital and...

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Perigon Life
30 Forensic Engineering
Insurance • Professional Services • Transportation • Consulting
Toronto
125 Employees

30 Forensic Engineering is one of Canada's largest independent, multidisciplinary, employee-owned forensic firms. The company provides world-class engineering and consulting expertise in areas such as biomechanics, fire codes, and collision reconstruction. Specializing in forensic engineering, loss mitigation, and remediation, they deliver detailed insights and actionable conclusions that empower clients in the insurance and legal industries to make decisions with confidence.

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30 Forensic Engineering
APEXA Corp
Insurance
Toronto
24 Employees
Hiring Now

APEXA began with a bold vision to digitally connect the Life Insurance Industry to simplify and standardize contracting and compliance for Advisors, MGAs, and Carriers. And we’ve done just that. What got us here can only be described as the Apex of collaboration. We brought together teams of experts from 9 leading MGAs and Carriers, industry compliance professionals, reputable service providers,...

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APEXA Corp
Max Insurance
Fintech • Insurance • Financial Services
Kitchener
44 Employees
1 Benefits

Personal property insurance at a fair price. That’s what we do at Max Insurance. Whether it’s your home, cottage, condo, or apartment, we believe it’s our duty to provide you protection for what matters most. We price each home with extreme precision based on its own merits rather than all of the homes within its community so you can stop...

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Max Insurance
Rakuten Group, Inc.
Digital Media • eCommerce • Fintech • Retail
22 Offices
29,334 Employees

Rakuten Group, Inc. is a Tokyo‑headquartered global technology and internet services group. It operates e‑commerce marketplaces (Rakuten Ichiba), fintech services including cards, banking and payments, digital content and advertising platforms, and mobile/communications services across 30+ countries. The company’s mission is to empower individuals and businesses through innovation, entrepreneurship and an integrated digital ecosystem of commerce, finance and media.

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Rakuten Group, Inc.
Munich Re
Insurance
30 Offices
44,000 Employees
7 Benefits

Munich Re is one of the world’s leading providers of reinsurance, primary insurance and insurance-related risk solutions. The group consists of the reinsurance and ERGO business segments, as well as the capital investment company MEAG. We are globally active and operate in all lines of the insurance business. Since our founding in 1880, we’ve been known for our unrivaled risk-related...

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Munich Re
Combined Insurance
3 Offices
5,191 Employees

Combined Insurance Company of America, a Chubb company, provides supplemental health, accident, disability, life, critical illness, cancer, and hospital insurance products to individuals, families, employers, and businesses. Its mission is to make supplemental insurance easier to understand while helping customers fill coverage gaps and manage out-of-pocket costs. Operating for more than 100 years, the company distributes benefits through trained agents,...

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Combined Insurance
Crawford & Company
Fintech • Insurance
58 Offices
7,718 Employees
38 Benefits Hiring Now

Based in Atlanta, GA Crawford & Company(R) (www.crawco.com) is the world's largest publicly listed independent provider of claims management and outsourcing solutions to carriers, brokers and corporates, with an expansive global network serving clients in more than 70 countries. The company’s shares are traded on the NYSE under the symbols CRD-A and CRD-B.

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Crawford & Company

Crawford & Company's Top Stability & Growth Strengths

Strong Market Position & Advantage: Crawford & Company is characterized as the world’s largest publicly listed independent provider of claims management and outsourcing solutions, with operations in 70+ countries and substantial claims volume handled annually.

Resilient & Sustainable Growth: Profitability and margins are improving, with stronger net income, higher operating earnings in Broadspire, and increased cash from operations despite flat-to-down consolidated revenue.

Diversified Revenue Streams: Multiple business lines—including Broadspire (TPA), International Operations, catastrophe response, managed repair (Contractor Connection), and digital platforms—contribute to performance and mitigate reliance on a single segment.

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