Simon’s practice concentrates on outsourcing, other complex services arrangements and procurement. 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, Blockchain, AgTech 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 to governments. Simon is often engaged to assist clients with complex interpretations of services agreements, including recently in connection with the impact of the COVID-19 pandemic on contractual performance.
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).
Areas of Expertise
Representative Work
- Cohere
Cohere announced it has raised US$500 million in its Series D financing round at a US$5.5 billion valuation
- Andgo Systems
Andgo Systems in its $5.6 million Series A financing round
- AtomVie Global Radiopharma
AtomVie in its spinout and Series A Financing
- Canada Drives
Canada Drives in its $40 million convertible equity financing led by goeasy
- Reamined Systems Inc.
Reamined in its $45.9 million acquisition by Information Services Corporation
- Signal 1
Signal 1 in its collaboration with Unity Health Toronto and TD Bank Group along with its US$10 million Seed financing
- Suncor Energy Inc.
Suncor Energy Inc. in its takeover of day-to-day operations at Syncrude oil sands mining joint venture
- The Board of Trustees of the WSIB Pension Plan Fund
The Board of Trustees of the WSIB Pension Plan Fund in the conversion of WSIB’s defined benefit, single employer pension plan to a jointly sponsored pension plan
- Suncor Energy Inc.
Suncor in its US$15 million investment in LanzaTech
- Q4 Inc.
Q4 Inc. in its strategic alliance with S&P Global Market Intelligence
- Bookmark Your Life
Bookmark Your Life in its strategic partnership with Moneris
- Drop Technologies Inc.
Drop Technologies Inc. in $44 million Series B round of capital financing
- JMI Equity
JMI Equity's $115 million investment in Vena
- Paycase Financial Corp.
Paycase Financial Corp. in its agreement with TMX’s Shorcan DCN to launch a new cryptocurrency brokerage service
- Ontario Pension Board
Ontario Pension Board in the outsourcing of its investment management operations to a $60 billion new investment management entity, the Investment Management Corporation of Ontario (IMCO)
Cohere announced it has raised US$500 million in its Series D financing round at a US$5.5 billion valuation
Andgo Systems in its $5.6 million Series A financing round
AtomVie in its spinout and Series A Financing
Canada Drives in its $40 million convertible equity financing led by goeasy
Reamined in its $45.9 million acquisition by Information Services Corporation
- Signal 1
Signal 1 in its collaboration with Unity Health Toronto and TD Bank Group along with its US$10 million Seed financing
- Suncor Energy Inc.
Suncor Energy Inc. in its takeover of day-to-day operations at Syncrude oil sands mining joint venture
- The Board of Trustees of the WSIB Pension Plan Fund
The Board of Trustees of the WSIB Pension Plan Fund in the conversion of WSIB’s defined benefit, single employer pension plan to a jointly sponsored pension plan
- Suncor Energy Inc.
Suncor in its US$15 million investment in LanzaTech
- Q4 Inc.
Q4 Inc. in its strategic alliance with S&P Global Market Intelligence
- Bookmark Your Life
Bookmark Your Life in its strategic partnership with Moneris
- Drop Technologies Inc.
Drop Technologies Inc. in $44 million Series B round of capital financing
- JMI Equity
JMI Equity's $115 million investment in Vena
- Paycase Financial Corp.
Paycase Financial Corp. in its agreement with TMX’s Shorcan DCN to launch a new cryptocurrency brokerage service
- Ontario Pension Board
Ontario Pension Board in the outsourcing of its investment management operations to a $60 billion new investment management entity, the Investment Management Corporation of Ontario (IMCO)
Latest Insights
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Osler Update Dec 11, 2023
AI governance: navigating the path ahead
Without question, during the past year, Canada has witnessed remarkable and radical change in the artificial intelligence (AI) sector, with the...
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Osler Update Oct 2, 2023
ISED’s Voluntary Code of Conduct on the Responsible Development and Management of Advanced Generative AI Systems
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Blog Mar 2, 2023
Retail Payment Activities Act: Draft regulations published for comment
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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
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.
Read more -
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”.
Read more -
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.
Read more -
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
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
