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Summarize
With 25 years’ experience in the United States and Canada in cutting-edge technology transactions, Matthew Flynn is a trusted advisor to technology customers and providers. Matt helps clients with structuring, drafting and negotiating successful commercial relationships, enabling speed to well-balanced deals that yield long-term value.

Overview

Matt’s practice focuses on technology transactions including cloud, fintech, AI, robotics, data management, privacy, strategic commercial partnerships, strategic sourcing, systems implementations, tech M&A, e-commerce, mobile payments, technology development and licensing. He also has deep experience in energy technology / cleantech including advanced metering infrastructure / smart meters, water remediation, oil sands extraction, carbon credits, geothermal, and EV.

Matt’s experience in Canada and the United States has been with blue chip law firms, and in-house with Accenture’s Legal & Commercial Group. He has worked on behalf of, and across from, a broad array of sophisticated and global players. Having represented both customers and providers of technology with their most complex matters, Matt’s understanding of the market gives him a seasoned and pragmatic approach to making deals.

Matt leads the Toronto technology transactions practice. Matt also leads the Bennett Jones California practice initiative, working on cross-border legal matters, having lived and worked in California for close to a decade as a complex tech transactions lawyer.

Matt founded and co-leads the Bennett Jones Fintech Group, converging legal expertise in commercial technology transactions, data management and privacy, financial regulation, securities, digital assets, tax, private finance, and fraud/asset recovery to accelerate the fintech industry, helping clients partner and profit throughout North America, Ireland and the United Kingdom.

As an industry expert, Matt is currently Vice Chair of the Fintech Substantive Law Committee at the International Technology Law Association. He also serves as Board Director at TechNation Health.

At his prior firm, Matt was the visionary for and co-lead of the Fintech Group—winner of services firm of the year at the 2017 Canadian Fintech Awards. Matt was the innovative architect of the Foundry: an innovative legal services platform serving the needs of fast growth / emerging companies, responsive to their need for agility and cost efficiency. Matt also led the Contract Management Solution, involving legal process re-engineering for the contract lifecycle, leveraging an outsourced model to help clients review and close contracts, and using data analytics to transform the in-house legal function to a high-level, strategic partner / trusted advisor to the business—while reducing costs per contract.

Client Work

Blue Ant Media in its go-public transaction by way of reverse takeover of Boat Rocker Media
Employment Hero Holdings, as Canadian counsel, in its acquisition of Humi Holdings, valued at over C$100 million
LSI Industries (Nasdaq; LYTS), a manufacturer of commercial lighting and display solutions, in its acquisition of Canada’s Best Store Fixtures, a provider of retail fixtures and custom store design solutions for grocery, quick service restaurant, c-store, banking and specialty retail environments
Shift4 Payments and its affiliates in its acquisition of of Eigen Development Ltd. and Eigen Holdings (U.S.) Corp. 
ActZero, a US-based provider of Managed Detection and Response (MDR) services, as Canadian counsel, in its sale to WatchGuard Technologies, a global leader in unified cybersecurity
Morrison Hershfield Group Inc. with the private company arrangement in its sale to Stantec Consulting Ltd.

Recognitions & Awards

Chambers Global

Band 4, Information Technology

Chambers Canada

Ranked, Information Technology

The Legal 500 Canada

Next Generation Lawyer, Technology

Canadian Legal Lexpert Directory

Repeatedly recommended, Computer & IT Law
 

Lexpert Special Edition—Canada's Leading Technology Lawyers

Recognized as a leading Technology lawyer

Lexpert Special Edition on Technology

Recognized as one of Canada's leading lawyers in Technology Transactions

Education & Bar Admissions

Education

  • King's College, English (Hons), 1993
  • University of Ottawa, LLB, 1996

Bar Admissions

  • Ontario, 1998
  • California, USA, 2001
  • Alberta, 2008

Insights

Fintech in Canada Q2 2025Blog

Fintech in Canada Q2 2025

August 25, 2025
Matthew FlynnAndrew BozzatoBernice B. Afriyie
Matthew Flynn, Andrew Bozzato & Bernice B. Afriyie
23andMes Data BreachBlog

23andMe's Data Breach: Key Takeaways

June 26, 2025
Stephen D. BurnsRuth E. PromislowJ. Sébastien A. Gittens
& 7 more
Fintech in Canada Q1 2025Blog

Fintech in Canada Q1 2025

May 16, 2025
Simon GrantMatthew FlynnKwang Lim
Simon Grant, Matthew Flynn & Kwang Lim

News, Events & Speaking Engagements

PlaceholderSpeaking Engagement

Matthew Flynn on Dealing with Digital Assets

May 5, 2022
Matthew Flynn
Matthew Flynn
PlaceholderIn The News

Matthew Flynn on Open Banking in National Post

February 4, 2019
Matthew Flynn
Matthew Flynn