Ai Insurance Organization is an award-winning commercial insurance and surety brokerage headquartered in Oakville, Ontario. The firm serves clients across every Canadian province except Quebec, and in select U.S. states through its sister entity, Ai Surety Bonding USA, LLC.
The brokerage specializes in surety bonds (contract and estate), builders risk, professional liability (E&O), D&O, cyber, and commercial lines. Clients include contractors of all sizes (startups through Fortune 500), transportation firms, developers, estates, and financial institutions.
Surety is the core strength, with contract surety and estate bonding accounting for 79% of total surety premiums. Primary surety markets are Trisura (68%) and Raise (23%). Commercial lines account for $5.5M and personal lines for $1.56M.
The organization operates a Managing Partner growth platform, runs on EOS, and uses HubSpot as its core CRM and sales engine. Ontario represents 68% of production, Alberta 18%, and BC 9%.
Surety bonds (bid, performance, payment, etc)
Builders risk / course of construction insurance
Errors & Omissions (E&O) / professional liability
Directors & Officers insurance
Cyber liability insurance
Commercial insurance (general liability, property, auto fleet)
Personal lines (home, auto, tenant, recreational)
International and cross-border surety bonding
Contractors and construction companies (all sizes)
Transportation firms
Real estate developers and infrastructure projects
Estates and fiduciary clients
Financial institutions with miscellaneous bonding needs
Professionals needing E&O, D&O, or cyber coverage
Complex commercial insurance placements
Surety-heavy contractor accounts (bid, performance, payment bonds)
Developer or infrastructure projects requiring builders risk
Broker cannot place risk elsewhere
Estate bonding requirements
Cross-border surety (Canada/U.S.)
Deep surety capacity across multiple market relationships
Places complex risk fast (most bond approvals in 1-3 business days)
Built for contractor-heavy portfolios
Award-winning brokerage with Managing Partner growth platform
International surety bonding capabilities
Commission on premiums
Surety placement fees
Broker margin on complex deals
Managing Partner program fees
2025 GWP: $9.62M (+22% YoY)
2025 new business: $4.87M (+44% YoY)
Surety concentration: Contract surety 54%, Estate bonding 25%
Geographic: Ontario 68%, Alberta 18%, BC 9%
Licensed across all Canadian provinces except Quebec
Leadership
Principal
Email: don@getcertain.ca
CEO, Insurance Division
Email: randy@getcertain.ca
Managing Partners
Email: andy@getcertain.ca
CSMO, Marketing
Email: aaron@getcertain.ca
COO, Operations & Compliance
Email: adrian@getcertain.ca
Director of Surety
Email: omer@getcertain.ca
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