Simon’s practice focuses on technology related commercial contracting and advice. He advises enterprises whose businesses rely on technology and complex services. He also advises technology suppliers ranging from large established software providers to early stage technology companies.
He leads a team providing innovative legal services models to the firm’s high growth technology clients pursuing a wide variety of cutting edge technology and business models, including FinTech, artificial intelligence, data analytics and eHealth. Simon has been lead counsel on projects across a broad range of industry verticals, including the technology, banking, pension, investment, healthcare, energy, telecommunication and retail sectors. He also advises on selling technology to governments and large enterprises.
Simon writes and lectures on various areas of technology law, both in public forums, firm seminars and client education venues. He is a past President of the Canadian Information Technology Law Association (IT.Can).
Representative Work
- Assisting provider of AI analytics in the utilities sector with reseller arrangement with Deloitte
- Assisting provider of AI enabled robotic technology with customer agreements
- Assisting provider of property tax services with negotiation of provincial government contracts through multiple renewals and negotiations and assisting with successful founder exit transaction
- Assisting provider of mortgage services with multiple agreements for foundation technology and services supporting product offering.
- Assisting provider of regional diagnostic imaging repository with agreement relating to its critical technology provider
- Assisting viral AI app developer with agreements for Discord channel and other commercial advice
- Assisting mobile game developer with its agreements with media owners (Sony and Mattel)
- Assisting leading social media company with product rollouts and general technology law issues for its Canadian business
- Assisting provider of Pension Administration Systems with agreement with major public sector pension plan
- Assisting provider of machine learning system for the electricity distribution industry with agreement for distribution of its applications
- Assisting with all aspects of negotiation with Neo Financial of a nationwide financial service offering
- Negotiating agreements relating to spin out of AI technology from major Canadian enterprise to establish multiple AI-based businesses
- Advising on procurement and negotiations for pension administration system for multi employer pension provider
- Advising on procurement and negotiations for pension administration system for single employer pension provider
- Advising leading provider of LLM AI systems on agreement with major Japanese technology company
- Advising regional credit union on acquisition of new credit card processing service provider
- Assisting large multi-national utility with negotiations related to its ongoing deployment of SAP ERP and related agreements with IBM
- Assisted with negotiation of renewal agreement for Canada wide e-prescribing system
- Assisted with negotiation of collaboration agreement between AI provider and TELUS Health
- Assisting provider of property assessment services software products with services agreement with Bearing Point for Irish property taxation authority
- Assisting large energy company with negotiations of licensing and other agreements related to its establishment of net zero drop in aviation fuel technology
- Assisting viral AI app developer with agreements for Discord channel and other commercial advice
- Assisting mobile game developer with its agreements with media owners (Sony and Mattel)
- Assisting leading social media company with product rollouts and general technology law issues for its Canadian business
- Assisting provider of Pension Administration Systems with agreement with major public sector pension plan
- Assisting provider of machine learning system for the electricity distribution industry with agreement for distribution of its applications
- Assisting with all aspects of negotiation with Neo Financial of a nationwide financial service offering
- Negotiating agreements relating to spin out of AI technology from major Canadian enterprise to establish multiple AI-based businesses
- Advising on procurement and negotiations for pension administration system for multi employer pension provider
- Advising on procurement and negotiations for pension administration system for single employer pension provider
- Advising leading provider of LLM AI systems on agreement with major Japanese technology company
- Advising regional credit union on acquisition of new credit card processing service provider
- Assisting large multi-national utility with negotiations related to its ongoing deployment of SAP ERP and related agreements with IBM
- Assisted with negotiation of renewal agreement for Canada wide e-prescribing system
- Assisted with negotiation of collaboration agreement between AI provider and TELUS Health
- Assisting provider of property assessment services software products with services agreement with Bearing Point for Irish property taxation authority
- Assisting large energy company with negotiations of licensing and other agreements related to its establishment of net zero drop in aviation fuel technology
Latest Insights
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Webinar Nov 6, 2024
Driving revenue while managing risk: a practical approach to customer contracts for emerging and high growth technology companies
Effective customer contracting drives revenue while effectively managing risk. Striking the right balance can reduce friction and facilitate...
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Webinar Sep 24, 2024
Navigating the future of payments
This seminar features Victoria Graham and Elizabeth Sale discussing, among other topics, various aspects of RPAA, including the registration process,...
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Webinar Aug 26, 2024
Navigating the legal landscape of AI commercial contracting
An exclusive Osler AI webinar on the intricacies of commercial contracting for AI products and services. This compelling one-hour session featuring...
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Osler Update Jun 5, 2024
The board’s oversight in the age of AI: ethics, compliance and competitive advantage
Artificial intelligence (AI) is reshaping the global business landscape at an almost dizzying speed. Many organizations, and their directors,...
Read more
Awards and Recognition
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Chambers Canada: Canada’s Leading Lawyers for Business: Recognized in Information Technology
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The Canadian Legal Lexpert Directory: Recognized in Computer & IT Law; Technology Transactions; Ontario’s top computer and IT lawyers in 2021
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Best Lawyers in Canada: Recognized in Information Technology Law; Technology Law; “Lawyer of the Year”, Technology Law (2023)
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Legal 500: Recognized in Technology, Media and Telecoms
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Who Who Legal: Recognized in Data – Information Technology; Fintech & Blockchain – Blockchain, Canada – Data; Canada – Fintech & Blockchain
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Lexpert Special Edition: Recognized in Technology and Health Sciences
Media Mentions
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Osler News Jun 29, 2023
29 Osler lawyers recognized in Lexpert Special Edition: Technology and Health 2023
Congratulations to 29 of our lawyers for their inclusion in the Lexpert Special Edition: Technology and Health 2023.
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Osler News Aug 25, 2022
Osler recognized in 2023 edition of Best Lawyers Canada
Congratulations to 170 of our lawyers who have been ranked across multiple practice areas and 13 who earned recognition as “Lawyer of the Year”.
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Osler News Jun 15, 2022
28 Osler lawyers recognized by Lexpert as leaders in Technology and Health Sciences
The Lexpert Special Edition: Technology and Health Sciences 2022 recognizes 28 Osler lawyers as leaders.
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Osler News Feb 19, 2021
Lexpert recognizes 21 Osler lawyers as technology leaders
Osler is pleased to announce 21 of our lawyers have been recognized as leading lawyers in the Lexpert Special Edition: Technology 2021.
Read more
Speaking and Writing
Speaking Engagements
Commercial Contracting for Innovation and Growth
Speaker, Calgary, November 30, 2022
Payments Law in Canada – An important update for all businesses
Speaker, April 28, 2022
Technology and Data in Construction Projects and Building Management – What you need to know
Speaker, November 23, 2021
Legal, Regulatory and Commercial Considerations in the use of AI Facial Recognition
Speaker, May 27, 2021
How Technology and AI are Transforming the Construction and Infrastructure Industry
Speaker, March 25, 2021
Cybersecurity from a Vendor/Service Provider Perspective
Speaker, November 10, 2020
Fintech Workshop: Negotiating with FIs
Speaker, Toronto, December 5, 2019
Streamlining Sales Related Contract Negotiations for Start-ups
Speaker, Toronto, October 7, 2019
Unlocking AI: Overcoming the legal and ethical challenges
Speaker, Wednesday, March 27, 2019
Technology Procurement Workshop – How Your Strategic Choices Affect Your Results
Speaker, Procurement, Osler Conference Centre, Toronto, April 26, 2016
Published Work
- Canadian Chapter, Global Legal Insights – AI, Machine Learning & Big Data 2022 (with Ted Liu and Sam Ip)
- Canada Chapter, Global Legal Insights – AI, Machine Learning & Big Data 2020, (with Ted Liu and Andre Perey)
- How to Effectively Use Contracts to Mitigate the Impact of Data Breaches, Ontario Bar Association Institute, February 2015
- Exclusions and Limitations of Liability (Osler Webinars and Client seminar), 2012-2014
- Cyber security considerations for public companies, Internet and E-Commerce Law in Canada, January 2014
- Cloud Computing: Minimizing Data Security Risks for You and Your Clients, co-presenter at the Ontario Bar Association’s TECHxpo, September 30, 2013
- Mobile Payments Navigating a New World, Osler Client Conference, April 12, 2012.
- Security in a Connected World, Osler client seminars 2011 and 2012.
- IT Contract Management, roundtable presentation jointly presented at Canadian IT Law Association Annual Conference, October 2011.
- IT Procurement: Best Practices for Issuers and Respondents, roundtable presentation jointly presented at Canadian IT Law Association Annual Conference, October 29, 2010
- Cloud Computing Contracting and the Spectrum of Risk, paper presented at the Canadian IT Law Association Annual Conference, October 23, 2009
- Preparing for eHealth Transformation Projects and New Infrastructure Ontario Approach (ITAC and Osler), panelist, October 21, 2009
- Payment Card System Security, Cardware 2009, June 17, 2009
Credentials
Education
- London School of Economics, LL.M.
- Osgoode Hall Law School, LL.B.
- Memorial University of Newfoundland, B.A.
Languages
- English
Professional Affiliations
- FinTech Working Group, Ontario Ministry of Finance
- IT.Can Law Association, former Board Member and President
- Canadian Bar Association
- Toronto Computer Lawyers Group, former Chair
- American Bar Association