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Insurance the way it should be.

Comprehensive commercial, bonding, personal and financial services from a team focused on clear advice, strong relationships and a straightforward insurance experience.

Trusted Insurance & Financial Services

At Oakway Insurance our commitment to ethical conduct, transparency, and a customer-centric approach isn't just a tagline; it's embedded in every facet of our organization. Our dedicated team thrives in an environment that encourages collaboration, integrity, and a tireless pursuit of excellence. This culture translates into a genuine and unwavering dedication to our clients' best interests, ensuring that every interaction with Oakway is characterized by trustworthiness and reliability. When you choose Oakway Insurance, you're choosing a partner who values not just your business but also the principles that make trust the cornerstone of our relationship.

CISRO Principles

Comprehensive Coverage for Every Need

Oakway Insurance takes pride in offering a comprehensive array of services designed to meet the diverse needs of our clients. Whether you're seeking bonding solutions to support your business ventures, require specialized commercial insurance coverage to safeguard your assets, or are looking for personalized and reliable personal insurance options, we've got you covered. Beyond these vital domains, we also extend our expertise to encompass financial services, providing valuable guidance and support in managing your financial risks and goals. Our commitment to excellence and customer-centric approach ensures that at Oakway Insurance, you'll find not just a range of services, but a trusted partner dedicated to helping you navigate the complex landscape of insurance and finance with confidence and peace of mind.

Commercial Insurance

Tailored comprehensive coverage to safeguard the interests and assets of commercial enterprises of all sizes.

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Bonding

In-house bonding department with unparalleled expertise in performance bonds, bid bonds, and surety solutions.

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Personal Insurance

Personalized and reliable personal insurance options for home, auto and life, giving you the confidence and security you deserve.

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Financial Services

Expert guidance in group benefits, life insurance, retirement planning, and financial risk management.

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Group Home & Auto Insurance Programs

At Oakway Insurance, we bring you the best-in-class Group Home & Auto insurance programs tailored to meet your unique needs.

Inquire About Group Programs

What members receive

  • Preferred group rates on home and auto
  • Bundled discounts across multiple policies
  • Dedicated service from a licensed broker
  • Programs for employers and associations

Let's Start a Conversation

We're ready when you are. Contact us today and receive a reply within 24 to 48 hours.

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35 Royal Group Crescent, Unit 2
Woodbridge, Ontario L4H 1X9

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Commercial Insurance

Tailored comprehensive coverage to safeguard the interests and assets of your business.

Protecting Your Business

Oakway Insurance stands as a distinguished leader in the insurance industry, renowned for its specialization in commercial insurance solutions. With a deep understanding of the unique challenges that businesses face, Oakway prides itself on tailoring comprehensive coverage to safeguard the interests and assets of commercial enterprises.

Our team of experienced experts collaborates closely with clients to craft customized insurance packages that address specific industry needs, whether it's protecting against liability, property damage, or other commercial risks.

Oakway's commitment to excellence in commercial insurance has earned us the trust of countless businesses, making us a reliable partner for safeguarding the financial well-being and stability of enterprises large and small.

Get a Commercial Quote

Bonding Solutions

In-house bonding expertise with unparalleled understanding of surety solutions.

Expert Bonding Services

Oakway Insurance distinguishes itself as a leading authority in the realm of bonding, thanks to its dedicated in-house bonding department. With a wealth of knowledge and experience, our team of experts possesses an unparalleled understanding of the intricacies and nuances of bonding solutions.

This specialized department enables us to provide tailored bonding services that cater to the unique needs of our clients. Whether it's performance bonds, bid bonds, or any other form of surety bonds, our in-house experts are well-equipped to craft solutions that instill confidence and trust in our clients' business endeavors.

This commitment to excellence has solidified Oakway Insurance's reputation as a trusted partner for businesses seeking top-tier bonding solutions.

Discuss Your Bonding Needs

Personal Insurance

A vital safety net for life's unpredictable moments.

Protecting What Matters Most

Personal insurance is of paramount importance as it serves as a vital safety net in life's unpredictable moments. It provides the financial protection and peace of mind necessary to navigate unexpected events such as accidents, illnesses, natural disasters, or the loss of valuable assets like homes or vehicles.

Personal insurance not only safeguards your financial stability but also ensures that you and your loved ones can access the necessary resources for recovery and rebuilding. It's an investment in your future security, offering reassurance that in times of adversity, you won't bear the burden alone.

Recognizing the significance of personal insurance is a responsible step towards securing your well-being and safeguarding your family's future. At Oakway Insurance we'll work tirelessly to ensure you have the right protection in place, giving you the confidence and security you deserve.

Get a Personal Quote

Financial Services

Expert guidance in group benefits, life insurance, and financial planning.

Group Benefits & Life Insurance

Group benefits and life insurance play a pivotal role in safeguarding the financial well-being and peace of mind for individuals and their families. Group benefits, often offered by employers, encompass a range of essential coverages, including health, dental, disability, and retirement plans.

These benefits not only enhance the overall job satisfaction and retention of employees but also ensure they have access to critical healthcare and financial support when needed.

Advisor reviewing a plan with clients

Life insurance, on the other hand, serves as a crucial safety net, providing financial protection to loved ones in the event of an untimely death. It eases the burden of funeral expenses and provides a financial cushion for beneficiaries, helping them maintain their quality of life.

Together, group benefits and life insurance contribute to a sense of security and stability, promoting the well-being and resilience of individuals and their families. Whether you're looking to invest wisely, plan for retirement, or secure your family's future, Oakway's financial services department is here to navigate the complexities and help you achieve financial success with confidence.

Speak With Our Team

About Oakway Insurance

Over 100 years of combined experience, one standard of service.

Built on Trust & Expertise

With over 100 years of combined experience, our mission is to provide our customers with the best coverage and services at the most competitive prices. Our experienced and knowledgeable staff works hard to ensure that every customer is taken care of and given the best possible service.

We are proud to be founded by six partners and long-time friends who, with their combined expertise and years of experience, are able to provide the highest quality of service and support.

Stop by Oakway Insurance today and see how we can help you.

Oakway mark

Oakway Insurance

Over 100 years of combined experience

Our Team

The people behind Oakway Insurance.

Executive Team and Partners

The leadership group behind Oakway Insurance.

John Orrico

John Orrico

CEO
Peter Defina

Peter Defina

President
Derek Toste

Derek Toste

CFO
Anthony Picillo

Anthony Picillo

COO
Chris Molella

Chris Molella

Senior Partner

Adam DiStefano

Senior Partner

Bonding

Our surety and bonding specialists.

Rob Rachiero

Bonding Specialist

Tim Haddad

Bonding Specialist

Account Executives

The brokers who look after your day-to-day needs.

Nick Caruso

Account Executive, Commercial Insurance

Adam Dobrofsky

Account Executive, Commercial Insurance

Daniel Picillo

Account Executive, Commercial Insurance

Anthony Mauro

Account Executive, Personal Home & Auto

Santino Fantauzzi

Account Executive, Personal Home & Auto

Adam Lofranco

Account Executive, Commercial Insurance

Christian D'Agostino

Account Executive, Commercial Insurance

Michael Roscetti

Account Executive, Commercial Insurance

Marco Principe

Account Executive, Commercial Insurance

Matthew Ferris

Account Executive, Commercial Insurance

Majd Mokabel

Account Executive, Commercial Insurance

Broker Compensation Disclosure

Transparency in how we are compensated for our services.

Our Role as Your Independent Broker

Oakway is an independent broker working on your behalf to secure competitive insurance products with coverage and terms that best protect your property and cover for liabilities you may incur.

The "independent" part of our role means we are not beholden to a single insurance company and your interests are always our priority. Our trained and licensed professionals: provide advice on markets offering the best price, coverage, and service; maintain your policies and manage mid-term changes; advocate for you in the case of policy issues and insurance claims.

The "broker" part of our job means we represent multiple insurance companies and provide services at costs insurers writing business directly would otherwise bear. Examples of assumed services and costs include: prospecting, marketing and business production; administrative and processing services; and travel expenses.

Additionally, Oakway provides value in technical expertise, local knowledge, customer relationships, and professional advice for you.

Compensation for our services and value-adds is paid in the form of a percentage of commission the insurer builds into your total premium. In the interest of transparency and full disclosure, we provide below a schedule of commissions sorted by insurer and product class.

InsurerPropertyAutomobileCommercial
Aviva*20%10% to 15%15% to 20%
Chubb20%12.5%15% to 20%
CoachmanN/A12.5%N/A
Definity Financial (Economical, Travelers Canada)*20%10% to 12.5%15% to 20%
Gore*20%10% to 12.5%15% to 20%
Intact Insurance*20%12.5%15% to 20%
Jevco*N/A12.5%N/A
Managing General Agents10% to 15%7.5% to 12.5%10% to 20%
Max Insurance20%N/AN/A
NordicN/A6% to 11% (Capped $310)5% to 10%
Northbridge20%12.5%N/A
OptimumN/AN/A15% to 20%
SGI Canada20%12.5%N/A
Sovereign General*20%10% to 12.5%15% to 20%
Unica20%12.5%15% to 20%
Wawanesa Mutual*20%7.5% to 12.5%15% to 20%

Commission percentages apply to new business and renewal policies and are paid to the broker annually.

*The success of insurance companies relies on business selected and priced to ensure total premiums exceed claims paid. To encourage growth of profitable business in desired classes, many insurers provide incentives under Contingent (Profit) Commission contracts. An asterisk is shown in the chart above for companies offering programs.

Based on proprietary formulas involving: overall premium volume; growth percentages; profitability (loss ratio); business retention rates; and other service initiatives, we may qualify for compensation under the Contingent Commission programs of insurers. In addition, our principals or other personnel may be invited to attend periodic educational or sales conferences sponsored by insurance companies.

For information specifically related to commitments made by insurance companies, you can refer to the Consumer Code of Rights and Responsibilities provided with your new business policy, or refer to the corporate website of an individual insurance company.

Please do not hesitate to contact us if you have any questions related to this declaration or any other matter involving your insurance.

CISRO Principles of Conduct

The standards of professional conduct every insurance intermediary in Canada is expected to meet.

What You Can Expect From Us

The Canadian Insurance Services Regulatory Organizations (CISRO) is a forum of the provincial and territorial authorities that regulate insurance intermediaries. Its Principles of Conduct for Insurance Intermediaries set out the minimum standards of conduct expected of brokers, agents and adjusters across Canada, so that customers are treated fairly at every stage of an insurance product's life.

Here is what those principles mean in practice at Oakway Insurance.

1. Compliance

We comply with all laws, regulations, rules and regulatory codes that apply to us.

2. Customers' Interests

We place your interests ahead of our own in how we develop, market, recommend, distribute and service products.

3. Conflicts of Interest

We identify, disclose and manage any actual or potential conflict of interest, and avoid arrangements where a conflict cannot be managed.

4. Advice

We ask the right questions to understand your needs, and give objective, accurate and thorough advice suited to the circumstances you disclose.

5. Disclosure

We give you relevant, timely and accurate information, explained clearly, so you can make an informed decision.

6. Product and Service Promotion

We promote products and services clearly and fairly, never misleadingly, with all necessary information disclosed.

7. Claims, Complaints and Dispute Resolution

We handle, or help handle, claims, complaints and disputes in a timely and fair manner.

8. Protection of Personal Information

We collect only the information needed to serve you, use it only for the purposes you consented to, and comply with privacy legislation.

9. Competence

We maintain our professional knowledge, complete our continuing education, and do not work beyond our level of experience.

10. Oversight

We are responsible for the conduct of any employee or third party involved in marketing, distributing or servicing your insurance.

The above is a plain-language summary. The full CISRO Principles of Conduct for Insurance Intermediaries, and the accompanying customer fact sheet, are published by CISRO and are available from us on request.

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The Health Reserve

Private Healthcare, Personally Delivered. Complete executive care for those who can't afford to wait in line.

The Health Reserve is Oakway's premium private healthcare solution powered by GroupBenefitz. It combines proactive health assessments, global medical coverage, and executive wellness services into one comprehensive package.

Complete Executive Care

Executive Assessment or Whole-Body MRI

Half-day multi-disciplined review with same-day results for member and spouse, each policy year. Includes:

  • Thorough health evaluation
  • Identify potential future risks
  • Long-term optimal health plan
  • Complements your family physician's care

Global Medical Care

Expedited Medical Treatment:

  • Leave-the-line access to top facilities worldwide
  • Up to $1M coverage for pre-planned treatment abroad
  • MRIs or CT Scans within 72 hours

Emergency Travel Protection:

  • Up to $5M coverage for unplanned medical treatment
  • 24/7/365 emergency travel assistance

Executive Wellness

Prevention, Recovery & Performance:

  • Telemedicine Virtual Care
  • Healthcare Navigation (Canada & abroad)
  • Pharmacogenetic DNA Testing
  • Nutrition & Diabetes Management
  • Virtual Rehabilitation & Athletic Therapy
  • EXAP Executive Coaching & Mental Health

Monthly Pricing

CoverageUnder 60Age 60-74
Single$411.56/mo$491.55/mo
Couple$823.13/mo$983.09/mo
Family$1,189.41/mo$1,293.54/mo

*Monthly premiums exclude 8% provincial tax. Rates valid September 1, 2026 to August 31, 2027. Executive Health Assessment or Whole-Body MRI available to member and spouse.

Clinic Network

Choose from leading executive health clinics across Canada:

Ontario: Medcan (Toronto, Oakville), Cleveland Clinic Toronto, TELUS Health (Toronto, Ottawa), La Vie (Ottawa, Kanata, Oakville), Durand Health (Hamilton), and more.

Other Provinces: TELUS Health and partner clinics in Vancouver, Calgary, Edmonton, Montreal, Quebec City, Winnipeg, Halifax, and St. John's.

Add-On: Medical Memberships

Access your private health clinic between assessments. Get ongoing care from a dedicated physician with on-site diagnostics. Ideal for continuity of care and longevity planning. Additional fees apply.

Ready for Elite Healthcare?

Discover how The Health Reserve can protect you and your family.

Book a Free Consultation →

Take Greater Control of Your Health with Medcan

Oakway Insurance & Oakway Financial Group are proud partners of Medcan, a global leader in proactive health and wellness services.

Medcan helps close the care gap with preventative healthcare solutions. Issues can be addressed sooner, leading to improved outcomes and long-term wellbeing.

Annual Health Assessment

Medcan's physician-led Annual Health Assessment is a total health blueprint to live well, for life. It includes investigations into mental health, cardiovascular and respiratory health, hearing, vision, fitness, and a dynamic blood and urine panel.

Up to 15 screening stations and tests for over 70 biomarkers, with same-day results, insights, and personalized recommendations.

Ongoing Care Memberships

Year-Round Care

Same or next-day appointments with a physician for urgent and episodic health needs. Includes after-hours medical advice from an on-call registered nurse.

Ideal for: Individuals or families looking for convenient medical care with flexibility.

Dedicated Care

Highly personalized continuity of care with a dedicated physician. 30-minute appointments and a comprehensive support team for proactive health management.

Ideal for: Those seeking a family doctor with personalized primary care experience.

M Care

Premium, concierge level of care with direct access to a dedicated physician, including after-hours and weekends. Includes annual treatment plans and genetic testing.

Ideal for: Those seeking proactive concierge-level primary care.

Enhanced Genetic Screening

With one of the largest teams of clinical genetic counsellors in Canada outside of a hospital setting, Medcan's genetic screening offerings deliver an extensive understanding of risks for hereditary cancers, disease, and many other health conditions.

  • Medication Effectiveness Screening: How your genetic makeup affects your reaction to medications
  • Heart Health Screening: Proactively manage cardiovascular disease risks
  • Cancer Prevention Screening: Identify genetic cancer risks
  • Whole Genome Sequencing: Comprehensive view of 4000+ genes

Exclusive Oakway Pricing

2026/27 program rates. Groups of 6 or more benefit from preferred rates with savings of up to 40%, plus centralized administration, a dedicated account manager and a dedicated customer service specialist.

SolutionYour PriceRetail Price
Annual Health Assessment$3,615$4,250
Year-Round Care Membership$1,215$1,430
Year-Round Care Membership, Family$2,270$2,675
Year-Round Care Membership + Annual Health Assessment$4,345$4,830
Dedicated Care Membership$3,760$4,175
Dedicated Care Membership + Annual Health Assessment$6,780$7,125
M Care Membership (includes Annual Health Assessment)$12,485$12,750
Genetic Screening (Medication Effectiveness, Heart Health or Cancer Prevention), each$890$1,050
Whole Genome Sequencing$5,985$6,300

*Rates shown are Oakway preferred rates for the 2026/27 program year, plus tax, and are confirmed with Medcan at enrolment. Pricing subject to change annually on November 1. Service availability varies by location; outside Ontario, Medcan services are delivered through affiliate clinics.

Clinic Locations

Toronto: 150 York St, Suite 1500  |  Oakville: 2275 Upper Middle Rd East, Suite 501  |  Kingsway  |  Collingwood: 40 Huron St, Unit 202  |  York Mills (opening fall 2026)  |  Muskoka (seasonal): 84 Joseph St, Port Carling

Medcan services also available across major cities in Canada including Vancouver, Calgary, Edmonton, Montreal, Ottawa, and Halifax through affiliate clinics.

Ready to Access Medcan?

Contact us to learn about exclusive Oakway pricing.

Book a Free Consultation →

Contact Us

We're ready when you are. Reach out today.

Let's Talk

Our team is here to help with all your insurance and financial needs. Contact us today and receive a reply within 24 to 48 hours.

Visit Us

35 Royal Group Crescent, Unit 2
Woodbridge, Ontario L4H 1X9

Send Us a Message

Fill out the form below and we'll get back to you shortly.