Halpenny Insurance Brokers

What Halpenny Insurance Brokers does

Halpenny Insurance Brokers is a privately held, Canadian-owned independent insurance brokerage founded in 1912 in Ottawa, Ontario. The company offers a comprehensive suite of insurance and risk management products across four core service areas: Commercial Insurance, Employee Benefits, Individual Life & Retirement, and Private Client Insurance, supplemented by specialized industry verticals (Construction, Healthcare, Public Sector, Municipality, Technology, Transportation, Real Estate, Manufacturing, Hospitality, and Financial Services) and Risk Consulting services. It serves both businesses and individuals, including high-net-worth private clients, with documented customers including the Federal Government of Canada, the City of Ottawa, and Community Health Centres in Eastern Ontario.

Halpenny operates as a fully independent broker, accessing 30+ insurance companies including AIG, Allianz, Aviva, Chubb, and Intact, which enables it to provide coverage options across diverse product lines such as general liability, property, professional liability, cyber, D&O, surety bonds, and medical malpractice. Its revenue model is commission-based, with commission rates ranging from 0-25% depending on coverage type, plus Contingent Profit Commission from certain insurers tied to growth, profitability, volume, retention, and service metrics. The company distributes products through direct field sales via licensed brokers, inside sales through consultation requests, and an independent brokerage network channel.

Following the December 2018 leadership transition when Richard Massie became President and majority owner, the company entered a period of accelerated expansion. Greg Fisk was appointed President in September 2025 to lead national expansion, and in January 2026 Halpenny acquired Windley Ely, a nationally respected leader in workers' compensation claims management, disability programs, and workplace safety solutions. The combined entity now operates in 6 Canadian cities — Ottawa, Toronto, Montreal, Vancouver, Calgary, and London — with regulatory standing including the National Master Standing Offer (NMSO) for the Canadian Federal Government (2021) and regulation by the Registered Insurance Brokers of Ontario (RIBO).

Name

Halpenny Insurance Brokers

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 a privately held, Ottawa-based independent insurance brokerage founded in 1912, offering commercial, employee benefits, life, and private client insurance across 10+ industry verticals to businesses and individuals in 6 Canadian cities.

Ownership category

akta.pro rank

Product category

Insurance Brokerage

NAICS

Insurance Agencies and Brokerages (52421), Insurance Agencies and Brokerages (524210)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

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

akta.pro secondary industry

Retail (Personal Lines) Insurance Brokerage (FSAEADAA)

Keywords

• Commercial insurance brokerage
• Employee benefits consulting
• Risk management services
• Private client insurance
• Independent insurance broker

Headquarters

HQ city

Ottawa

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, Infrastructure, Technology or R&D

Revenue model

1. Insurance Brokerage Commissions: Halpenny earns commission income from insurance products placed with their represented insurers. Commission ranges vary by product type and insurer, typically 0-22% depending on coverage type. They also earn Contingent Profit Commission from certain insurers based on growth, profitability, volume, retention and services provided.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels5 records

Core offering

Halpenny Insurance Brokers is an independent insurance brokerage that places commercial, personal, and specialty insurance coverage on behalf of businesses and individuals by representing more than 30 insurance carriers. Core offerings span four service lines—Commercial Insurance, Employee Benefits, Individual Life & Retirement, and Private Client Insurance—supplemented by Risk Consulting services including insurance audits, contract review, claims advisory, and property appraisals.

Product overview

Halpenny Insurance Brokers operates as an independent insurance brokerage offering a comprehensive suite of insurance and risk management products across commercial, personal, and specialty lines. The core portfolio consists of four main service areas: Commercial Insurance (covering property, liability, vehicles, and professional lines), Employee Benefits (group health, life, retirement plans), Individual Life & Retirement (personal insurance products), and Private Client Insurance (high-net-worth personal coverage). These are supplemented by specialized industry-specific products including Municipal Insurance, Technology E&O, Healthcare Insurance, Construction Insurance, Real Estate Insurance, Transportation Insurance, and Hospitality Insurance. The company also provides Risk Consulting services including insurance audits, contract review, claims advisory, and property appraisals. Following the 2026 acquisition of Windley Ely, the company expanded to offer workers' compensation claims management and disability programs, operating from six Canadian cities including Ottawa, Toronto, Montreal, Vancouver, Calgary, and London.

Differentiator

Problem solved

Functional benefit

Products and services

• Commercial Insurance Comprehensive business insurance solutions for commercial clients covering general liability, property insurance, commercial vehicles, builders risk, professional liability, marine/transit, environmental liability, directors and officers liability, cyber liability, surety bonds, and risk identification and assessments to protect businesses and employees.
• Employee Benefits Group benefits and retirement solutions for employer groups including health insurance, dental, vision, disability, life insurance, group retirement savings plans, and employee assistance programs (EAP) covering mental health resources and counseling.
• Individual Life & Retirement Personal insurance products for individuals including term life insurance, permanent life insurance, disability insurance, critical illness insurance, key person insurance, and individual health and dental benefits, plus access to legal, financial, and tax planning experts.
• Private Client Insurance Customized personal insurance protection for high-net-worth individuals covering home, vehicles (including classic/vintage and high-value), boats, cottages, condos, umbrella policies, and personal belongings, supported by 24/7 emergency claims service.
• Risk Consulting Risk management and insurance advisory services for large enterprises including insurance audits, contract review, claims advisory, construction advisory, lender advisory, and property appraisals.
• Workers' Compensation Claims Management & Disability Programs (Windley Ely) Workers' compensation claims management, disability programs, and workplace safety solutions for corporate clients across Canada, delivered through the Windley Ely operation following the January 2026 acquisition.

Quantifiable outcome

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

Named customers6 records

Segments11 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature1 record

Partnerships

One partnership is on record.

• Windley ElycoreStrategic or Co-development Partner · 14 January 2026Strategic acquisition bringing together two organizations with deep expertise in insurance. Windley Ely is a nationally respected leader in workers' compensation claims management, disability programs, and workplace safety solutions. The combined entity operates in 6 Canadian cities: Ottawa, Toronto, Montreal, Vancouver, Calgary, and London. Windley Ely continues to operate under its existing brand while accessing Halpenny's broader insurance platform.

Scale indicators5 records

Recent moves6 records

Expansion highlights5 records

Broad incumbents

• HUB International: Large global insurance brokerage with significant Canadian operations across commercial, personal, and specialty lines. Comparable to Halpenny in independent brokerage positioning but at much greater scale with broader geographic reach.
• Aon Canada: Canadian arm of global insurance and reinsurance broker Aon plc. Comparable to Halpenny in commercial and specialty insurance brokerage but at vastly larger scale, with broader risk consulting and reinsurance capabilities.
• Marsh Canada: Subsidiary of Marsh & McLennan, one of the world's largest insurance brokers. Comparable to Halpenny in serving large commercial and public sector clients; notably, Halpenny's new President Greg Fisk joined from Marsh Canada's Corporate Segment, signaling direct talent overlap.

Direct peers

• Cowan Insurance Group: Canadian independent insurance brokerage offering commercial, personal, group benefits, and surety across multiple provinces. Closely comparable to Halpenny in independent multi-line model and Eastern Canadian origins.
• CapriCMW Insurance Services: Western Canadian independent insurance brokerage serving commercial, personal, and group benefits clients. Comparable to Halpenny as an independent, full-service multi-line brokerage with a regional origin and growth-oriented M&A track record.
• BFL Canada: Canadian specialty insurance broker focused on commercial and complex risks across construction, real estate, hospitality, and other verticals. Closely comparable to Halpenny's specialty commercial expertise, particularly in marine, cyber, professional, and environmental lines.
• Lloyd Sadd Insurance Brokers: Western Canadian independent insurance brokerage with commercial, personal, and group benefits practices. Comparable to Halpenny as an independent, multi-line Canadian brokerage with strong regional roots.
• BrokerLink: One of Canada's largest independent insurance brokerages, wholly owned by Intact Financial Corporation. Operates multi-line across personal and commercial with a multi-carrier model — directly comparable to Halpenny's independent brokerage positioning, and notable given Halpenny's disclosed operating loan from Intact.
• Westland Insurance Group: Canadian independent insurance brokerage offering commercial, personal, and specialty lines across multiple provinces. Closely comparable to Halpenny in independent multi-carrier model, multi-line product mix, and growth-via-acquisition strategy.
• Acera Insurance: Western Canada-based independent insurance brokerage offering commercial, personal, group benefits, and surety. Comparable to Halpenny as a regional Canadian independent broker that has expanded nationally through acquisitions.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• Xx.com/HalpennyLtd

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 Insurance Brokers