HALPENNY TORONTO LTD.

What HALPENNY TORONTO LTD. does

Halpenny Insurance Brokers Ltd. is an independent Canadian insurance brokerage founded in 1912 in Westboro, Ottawa, and currently headquartered at 55 Metcalfe Street, Ottawa. The firm operates as a multi-line brokerage serving commercial, public-sector, and individual clients across 10 industry verticals (Construction, Healthcare, Public Sector, Municipality, Technology, Transportation, Hospitality, Manufacturing, Real Estate, and Financial Services). Core product lines include Commercial Insurance, Private Client Insurance, Employee Benefits, Individual Life & Retirement, and Risk Consulting, delivered through specialized sub-brands Halpenny Specialty Risk and Halpenny Benefits & Retirement Specialists, with the recently acquired Windley Ely brand adding workers' compensation claims management and disability program services.

The business model is commission-based: Halpenny places business with 35+ insurance carriers (including AIG, Allianz, Aviva, Chubb, Intact, and Lloyd's) and earns commission ranging from 0-12.5% on auto to 0-25% on cyber/crime and other specialty lines, plus contingent profit commissions from select carriers tied to growth, retention, and service metrics. Distribution is relationship-led via direct sales from six Canadian offices (Ottawa, Toronto, Montreal, Vancouver, Calgary, London), supplemented by a toll-free consultation line (1-800-635-3508) and a website consultation form. Go-to-market combines enterprise field sales (Halpenny Specialty Risk targeting large enterprises, government, and publicly traded companies) with sales-led B2B and direct-to-consumer motion.

Following the December 2018 leadership transition with Richard Massie as President and majority owner, Halpenny underwent a structural transformation that drove headcount growth, the 2021 National Master Standing Offer (NMSO) award from the Federal Government, recognition by Insurance Business Canada as a Top 50 Growing Brokerage, the launch of the Benefits & Retirement division in 2023, the appointment of Greg Fisk (ex-Marsh Canada) as President in September 2025, and the January 2026 acquisition of Windley Ely. The company is privately held by Richard Massie and leadership partners, regulated by RIBO, and has an operating loan from Intact Insurance disclosed on its website.

Name

HALPENNY TORONTO LTD.

Legal name

Halpenny Insurance Brokers Ltd.

Website

https://halpenny.com

Company type

Private

Founded year

1912

Operating status

Operating

Headcount range

11–50 employees

Short description

Halpenny Insurance Brokers is an independent Canadian insurance brokerage, founded 1912 in Ottawa, placing commercial, personal, employee benefits, life and retirement, and risk consulting coverage with 35+ carriers across 6 Canadian cities and 10 industry verticals.

Ownership category

akta.pro rank

Product category

Insurance Brokerage Services

NAICS

Insurance Agencies and Brokerages (52421)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Specialty Insurance Brokerage (Marine, Aviation, Cyber, Professional Lines) (FSAEADAJ)

akta.pro secondary industry

Individual Health Insurance Brokerage & Distribution (FSAIAEAL)

Keywords

• Commercial insurance brokerage
• Personal insurance brokerage
• Employee benefits consulting
• Risk management services
• Group retirement planning

Headquarters

HQ city

Toronto

HQ country

Canada

HQ region

North America

Offices6 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Insurance Broker Commissions: Brokerage compensation earned as commission on new and renewal insurance business placed with insurers. Commission ranges vary by coverage type: Auto (0-12.5%), Property/Boiler/Liability (0-22%), Excess/Umbrella (0-22%), D&O/E&O (0-22%), Cyber/Crime/Other (0-25%). Some insurers provide Contingent Profit Commission based on growth, profitability, volume, retention, and increased services.

Pricing tiers

Go-to-market motion3 records

Distribution channels5 records

Marketing channels7 records

Core offering

Halpenny Insurance Brokers is an independent insurance brokerage that places commercial and personal insurance, employee benefits, group retirement plans, and individual life and retirement coverage on behalf of clients with 35+ insurance carriers. The firm also delivers risk consulting services including insurance audits, contract review, claims advisory, construction advisory, and lender advisory for large enterprises, government agencies, municipalities, and publicly traded companies. It serves 10 industry verticals across 6 Canadian cities through its Halpenny Specialty Risk and Halpenny Benefits & Retirement Specialists divisions plus the acquired Windley Ely brand.

Product overview

Halpenny Insurance Brokers is a multi-line insurance brokerage providing a comprehensive portfolio of insurance and risk management solutions. The core offerings consist of Commercial Insurance (covering general liability, property, vehicles, professional liability, and marine), Private Client Insurance (high-value personal coverage for homes, vehicles, and specialty assets), Employee Benefits (group health, dental, vision, life, and retirement plans), Individual Life & Retirement (personal life, disability, critical illness, and key person coverage), and Risk Consulting (insurance audits, contract review, claims and construction advisory for large enterprises and government entities). The company operates across 10 industry verticals: Construction, Healthcare, Public Sector, Municipality, Technology, Transportation, Hospitality, Manufacturing, Real Estate, and Financial Services. Halpenny operates specialized divisions including Halpenny Specialty Risk (complex national accounts and federal government services via NMSO) and Halpenny Benefits & Retirement Specialists. Following the January 2026 acquisition of Windley Ely, the company now operates under two brands serving 6 Canadian cities (Ottawa, Toronto, Montreal, Vancouver, Calgary, and London) with workers' compensation and disability program capabilities.

Differentiator

Problem solved

Functional benefit

Brands

• Halpenny Benefits & Retirement Specialists: Division specializing in employee benefits and group retirement plans
• Halpenny Specialty Risk

Products and services

• Commercial Insurance Comprehensive insurance coverage for businesses including general liability, property insurance, commercial vehicles, builders risk, equipment breakdown, professional liability, marine transit, and commercial automobile fleets. Tailored insurance solutions to keep businesses and employees secure for the long term.
• Private Client Insurance Customized protection for high-net-worth individuals covering homes, vehicles, classic/vintage cars, boats, cottages, condos, motorcycles, rental properties, and umbrella policies. Designed to meet unique needs with comprehensive security for families' most important assets.
• Risk Consulting Risk management and insurance solutions for large enterprises, government agencies, municipalities, and publicly traded companies including insurance audits, contract review, claims advisory, construction advisory, and lender advisory services.
• Employee Benefits Employee benefits and group retirement savings plans covering health insurance, life insurance, medical services, prescription drugs, dental, vision, disability, critical illness, and out-of-province emergency travel insurance. Benefits team has over 50 years of combined experience.
• Individual Life & Retirement Individual insurance solutions including term life, permanent life, disability, critical illness, key person insurance, and individual health and dental benefits that complement group plans. Also provides access to legal, financial, and tax planning experts.
• Construction Insurance Insurance solutions for the construction industry including project-specific errors and omissions coverage and surety bonds for contractors. Covers property, liability, workers compensation, bonds, environmental, and professional liability.
• Healthcare Insurance Insurance coverage for healthcare organizations including hospitals, medical clinics, medical device manufacturers, pharmaceutical companies, research facilities, diagnostic labs, retirement and long-term assisted living homes. Features medical malpractice liability coverage.
• Public Sector Insurance Insurance solutions for public entities including professional liability, wrap-up liability, umbrella and excess liability, project-specific pollution, fiduciary liability, and builders risk coverage.
• Municipality Insurance Insurance coverage for municipalities and public assets including professional liability, travel accident, legal expense, bonding and surety, and accidental death and dismemberment coverage. Halpenny has been engaged in municipal risk management since 1945.
• Technology Insurance Technology insurance including technology errors and omissions coverage protecting against claims from mistakes, negligence, software bugs, data breaches, and service-related failures. Includes D&O coverage and cyber insurance.
• Transportation Insurance Insurance for transportation and logistics companies covering transit/cargo, marine liability, aviation liability, crime, and commercial automobile/fleet coverage. Includes cross-border freight, resource hauling, and last-mile deliveries.
• Hospitality Insurance Insurance for hospitality businesses including abuse liability coverage and employment practices liability insurance. Covers casual eateries to upscale hotels with guest-facing environment risks.
• Manufacturing Insurance Insurance coverage for manufacturers addressing equipment breakdown, environmental/pollution liability, directors and officers liability, and commercial general liability. Covers precision machining, large-scale production, and custom fabrication.
• Real Estate Insurance Insurance for real estate investments covering property, business interruption, equipment breakdown, environmental/pollution liability, directors and officers liability, and commercial general liability. Serves property owners, managers, and developers.
• Financial Services Insurance Strategic insurance solutions for financial institutions including cyber coverage for financial loss due to cyber attacks or privacy breaches. Serves lenders, asset managers, family offices, private equity, real estate investment firms, and other financial services.

Quantifiable outcome

• Largest independent insurance broker in Ottawa and Eastern Ontario
• +2 more outcomes

Named customers5 records

Segments12 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• Windley ElycoreStrategic or Co-development Partner · 14 January 2026Windley Ely is a nationally respected leader in workers' compensation claims management, disability programs and workplace safety solutions. The acquisition creates a new Canadian leader in corporate insurance, risk management, and claims advisory services operating in 6 Canadian cities: Ottawa, Toronto, Montreal, Vancouver, Calgary & London. Windley Ely will continue operating under its existing name and brand for the foreseeable future. CEO Dan Pompilii leads Windley Ely which aligns with Halpenny's corporate insurance, risk management, employee benefits, affinity and private client insurance offerings.

Scale indicators5 records

Recent moves7 records

Expansion highlights6 records

Broad incumbents

• Arthur J. Gallagher & Co. (Canada): Global insurance brokerage with substantial Canadian operations serving commercial, public sector and specialty clients. Competes for the same Specialty Risk and benefits mandates that Halpenny's NMSO and municipal practice target.
• Marsh Canada (Marsh McLennan): Canadian arm of global brokerage Marsh McLennan, serving large enterprises, government and specialty risks. Competes with Halpenny Specialty Risk for institutional and government accounts but operates at vastly larger global scale.
• Hub International Canada: North American insurance brokerage with significant Canadian operations serving commercial and personal clients across multiple provinces. Comparable as a multi-line broker with M&A-driven national expansion strategy.
• Aon Canada (Aon plc): Global professional services firm with major Canadian insurance brokerage operations serving large commercial, government and specialty clients. Overlaps with Halpenny's Specialty Risk, public-sector and construction verticals.

Direct peers

• Cowan Insurance Group: Privately held Canadian insurance brokerage providing commercial, personal, employee benefits and specialty coverage to businesses and individuals. Closely comparable in scope, Canadian independent ownership, and benefits/specialty mix.
• Westland Insurance: Major Western-Canada-headquartered independent insurance brokerage offering personal, commercial, specialty and benefits coverage with a strong acquisition-led growth strategy. Comparable as a Canadian independent broker pursuing multi-line and multi-region expansion.
• BrokerLink: One of Canada's largest independent insurance brokerages, multi-line commercial and personal coverage with national branch footprint. Directly comparable as a Canadian, non-carrier-affiliated broker competing for the same commercial and high-net-worth clients.
• BFL Canada: Canadian-owned specialty commercial insurance brokerage serving complex and large-enterprise clients across construction, real estate, hospitality, manufacturing and public sector. Closely comparable as a Canadian independent specializing in complex commercial risks.
• Jones DesLauriers Insurance (JDI): Canadian-owned independent brokerage providing commercial, personal and specialty insurance with strong presence in Ontario and Quebec. Comparable as a privately held Canadian independent broker with commercial and specialty focus.
• Acera Insurance: Canadian independent brokerage formed through roll-up of regional brokerages offering commercial, personal, life and benefits coverage nationally. Comparable independent Canadian broker pursuing scale via acquisitions and multi-product offering.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks7 records

Key highlights7 records

Customer concentration

• Instagraminstagram.com/halpennyinsurance
• LinkedInlinkedin.com/company/halpenny

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Profiles7 records

Subsidiaries1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about HALPENNY TORONTO LTD.