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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 payments and fintech, technology transactions including cloud, AI, robotics, data management, privacy, strategic commercial partnerships, strategic sourcing, systems implementations, tech M&A and private equity, 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, including most major FIs in Canada, the US and the UK. 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 founded and co-leads the Bennett Jones Fintech Group, converging legal expertise in payments, 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 client's partner and profit throughout North America, Ireland and the United Kingdom.

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.

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

Client Work

FISERV with its multi-year Strategic Managed Services program agreement with TD Bank Group, where TD Merchant Solutions will utilize Fiserv technology, including Clover, the world's smartest point-of-sale system, for its merchant business
FISERV with its acquisition of part of TD’s merchant processing business in Canada
FreshBooks with its transformational launch of FreshBooks Payments through a strategic partnership with Stripe, enabling business owners send payments-enabled invoices, manage payments and track revenue–all from within FreshBooks's platform
Shift4 Payments in its acquisition of Givex Corp., a global provider of gift cards, loyalty programs and point-of-sale solutions in an all-cash going private transaction valued at C$200 million  

Paylocity with rolling out its HR and payroll solution in Canada

Employment Hero Holdings, as Canadian counsel, in its acquisition of Humi Holdings, valued at over C$100 million

Recognitions & Awards

Chambers Canada

Fintech

Chambers Global

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

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

AI Notetaking in the BoardroomBlog

AI Notetaking in the Boardroom

September 17, 2025
Stephen D. BurnsMatthew FlynnJ. Sébastien A. Gittens
& 2 more
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