Authors
Partner, Corporate, Toronto
Partner, Technology, Toronto
Partner, Corporate, Toronto
Partner, Corporate, Montréal
Partner, Corporate, Toronto
Partner, Competition/Antitrust and Foreign Investment, Toronto
Partner, Technology, Toronto
Partner, Competition, Trade and Foreign Investment, Toronto
Partner, Privacy and Data Management, Montréal
Partner, Disputes
Head: White-Collar Defence, Montréal
Partner, Financial Services, Toronto
Partner, Corporate, Montréal
Partner, Emerging and High Growth Companies, Toronto
Partner, Emerging and High Growth Companies, Calgary
Partner, Emerging and High Growth Companies, Toronto
Associate, Competition, Trade and Foreign Investment, Toronto
Articling Student, Toronto
Letter from the Editor
Welcome to the Summer 2026 edition of Osler’s PE Points newsletter, bringing you the latest legal insights and important news to keep you up to date on the ever-evolving private equity landscape.
This edition centers on a theme that has quietly become a compelling story in Canadian PE: essential services. As sponsors reassess capital allocation in a market shaped by AI-driven disruption of traditional software models and constrained public exit channels, non-discretionary services businesses — from pest control to residential and commercial services — are increasingly attracting institutional capital. Our Leader’s Corner article features Simon Leith of Homepro Pest Control, who shares his journey from Osler M&A lawyer to essential services entrepreneur, along with practical insights on permanent capital models, acquisition strategy and the discipline required to build a durable services platform.
Our Tech Insights article builds on Technology partner Sam Ip’s earlier work on AI transactions, translating the emerging challenges of AI-related deals into practical structuring guidance for private equity sponsors. From AI-linked earn-outs and MAC clauses to representation and warranty considerations and diligence sequencing, the piece examines how the traditional PE playbook is evolving as AI reshapes both the value and the risk profile of technology-driven targets.
Rounding out the edition, our Legal Developments section covers a series of practical updates for sponsors, portfolio companies and their advisors: the mechanics of co-investment transactions and what investors should know before participating; the emergence of continuation vehicles as a mainstream liquidity solution for sponsors navigating extended hold periods; the shifting Canadian M&A landscape as shaped by the country’s accelerated defence build-up and new procurement priorities; and key takeaways from Osler’s 2025 Deal Points Report on private capital financings, offering a data-driven look at market terms and trends.
If you would like to discuss any of these items, or a PE-related transaction you are considering, please reach out to us. And if there is a topic you would like us to cover in a future newsletter, we would love to hear from you.
—Brian Gray, Chair, Private Equity
Leader’s Corner
Simon Leith’s journey from Bay Street lawyer to building a pest control business utilizing permanent capital
Technology Insights
The PE playbook: translating AI risk into deal structure
Osler Deal Points Report finds Canada’s venture recovery was uneven in 2025 – BetaKit
Industry Spotlight
Canada’s defence build-up and the new M&A playbook
Legal Developments
Continuation vehicles in private equity: structuring, governance and execution
Co-investments: what investors should know
2025 Deal Points Report: Venture Capital Financings
Osler ranked #1 in H1 2026 M&A league tables
Bloomberg names Osler the top Canadian law firm for Canada announced deals by volume.
Read more
