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Matthew Flynn

Partner

Partner | Email

T: 416.777.7488

Email

Toronto

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Flynn Matthew
 
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T: 416.777.7488


Email

Toronto

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  • Education
  • Bar Admissions
  • Select Experience
  • Recent Recognition
  • Insights, News & Events
  • Related Services
  • Select Experience
  • Recent Recognition
  • Insights, News & Events
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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.

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.

Education

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

Bar Admissions

Ontario, 1998 California, USA, 2001 Alberta, 2008

Select Experience

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.
Capvest Partners in its acquisition of Recochem, a Quebec based manufacturer of aftermarket transportation and household fluids
Clearpath Robotics Inc., a leader in autonomous robotics, in its sale to Rockwell Automation, Inc.
Betr Holdings, Inc. in its acquisition of the Chameleon platform, a full suite of gaming solutions, including Player Account Management, sports betting engine, and casino management, from FansUnite Entertainment Inc.
Assisted client out of Silicon Valley in all aspects of setting up an AI large language model enterprise in Canada, including funding, navigating the regulatory landscape, and preparing for commercial launch
An award-winning provider of an AI model risk management platform for all of its commercialization efforts, including partnering with a top-tier American consulting firm to deploy AI in the firm's client offerings
A major public transportation provider, with the procurement of operational technology cybersecurity services to 'harden' the client's cyber assets, including drafting and negotiating a complex services agreement across from eight service providers
A leading global fintech with its embedded banking project, enabling the client to offer banking services "in-App" on a white-labelled basis. Initiative included highly complex data sharing mechanics
A mining technology service provider with all aspects of commercializing its platform (hardware and software) that enables engineers and geologists to collect then process 3D point cloud data into useful geological measurements
Assisting a services provider of an AI-powered sales-lead generation platform in navigating the Canadian regulatory landscape in respect of privacy, CASL, and online, digital prospecting
A Canadian fintech company with selling its AI-powered services into major North American and U.K. banks
PowerSchool in its acquisition of Chalk.com Education
Datasite LLC, a portfolio company of CapVest Partners LLP, in its acquisition of Firmex Inc., a leading virtual data room and subscription file-sharing provider
True Wind Capital and its portfolio company, Transflo, in Transflo's approximately $20-million acquisition of Microdea, a document management software company in the transportation and logistics sector
A global, cloud-based, AI powered Managed Security Services Provider with its purchase of a Canadian company and subsequent scaling of Canadian operations: commercial, employment, tax, privacy, and other matters
A software-as-a-service platform with various agreements to commercialize its affective intelligence engine that applies advanced signal processing and deep learning artificial intelligence models to predict physiological and psychological affects: including measuring, tracking and recording general wellness based on facial blood flow
A leading Canadian enterprise with the rollout of an EV Charging solution, coupled with 5G infrastructure and battery generators
A leading global robotics company, with its role as systems integrator building out one of the world’s first comprehensive automated warehouse solutions. Led a multi-jurisdictional team that structured, drafted and negotiated contemporaneous agreements for the procurement of robotic-based warehouse automation equipment and services, and AI-powered robotic picking arms, and for the provision of a fully-integrated Warehouse-as-a-Solution to a leading on-demand convenience store
A leading global robotics company, with its Canadian rollout of Robots-as-a-Service offerings: Pepper – the first humanoid with an emotion engine, and Whiz – an AI-powered autonomous cleaning robot
BSM Technologies Inc., with its commercial telematics-focused agreements, and in its approximately $117.3 million sale to Geotab Inc. by way of plan of arrangement
Freshbooks, with its strategic commercial agreements including with North American and U.K. banks, Google, Apple, Visa, Stripe, and dozens of others
Sensibill, a leading Canadian Fintech company, with services agreements providing its digital receipts solution to major North American banks
ThinkData Works, with: service agreements for its data cleansing, formatting and analysis platform, including for a major Canadian bank and for a global commercial real estate industry player; a data marketplace agreement; and a strategic financing
A major public transportation provider, with complex services agreements underpinning the procurement of IT services and a WiFi managed solution (including data analysis)
Garner Distributed Workflow, with global services agreements for its major projects logistics platform with several multi-national energy companies
BMW, with several technology related agreements, including procurement of a dealer management system, rollout of its connected car offering in Canada, and a data sharing agreement across its enterprise
A major North American utility, with the procurement and deployment of a $1.3-billion advanced metering infrastructure. Structured, drafted and negotiated all aspects of the transaction, from RFP through to the definitive agreements.
A provincial gaming organization, with its RFP and services agreement for the procurement of a content management system and development services for online and mobile applications

Recent Recognition

Chambers Canada
Ranked, Information Technology
Chambers Global
Band 4, Information Technology
The Legal 500 Canada
Next Generation Lawyer, Technology
Canadian Fintech Awards
Visionary and Co-Lead of Fintech Services Firm of the Year
Canadian Legal Lexpert Directory
Repeatedly recommended, Computer & IT Law
 
Best Lawyers in Canada
Recognized, Technology Transactions
Lexpert Special Edition on Technology
Recognized as one of Canada's leading lawyers in Technology Transactions
Who's Who Legal: Fintech & Blockchain
Recognized as a leading lawyer: Fintech
Who's Who Legal
A Canadian leading practitioner in Fintech
Who's Who Legal: Canada
Banking

Insights, News & Events

Client Work

Blue Ant Media Announces Go-Public Transaction By Way of Reverse Takeover of Boat Rocker Media

March 27, 2025
       

Client Work

LSI Industries Acquires Canadas Best Holdings

March 24, 2025
       

Blog

Trends and AI Potential in Proptech

February 20, 2025
       

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IT & Business Services
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Power & Renewables
Mergers & Acquisitions
Retail, Consumer & Luxury Law
Artificial Intelligence
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