Wendy Gross

Wendy Gross

Partner, Technology

Chair: Commercial Technology Transactions

Key Contact: Outsourcing

Key Contact: Artificial Intelligence

Key Contact: Fintech

Contact Information


tel: 416.862.6737



Wendy is Chair of Osler’s Technology Group and provides trusted, strategic counsel to some of Canada’s most well-known companies in the financial services and payments, retail, e-commerce, AI, technology, telecommunications, health, energy and transportation sectors.

Wendy specializes in outsourcing and other complex corporate and commercial transactions relating to technology products, services and business processes, including in core functions such as technology and operations, enterprise risk management, payment systems, credit card and loyalty programs, data analytics, cloud arrangements, procurement, logistics and supply chain management.

She keeps her clients at the forefront of Canada’s regulatory environment as it applies to new and emerging developments in technology, helping clients anticipate and stay abreast of important changes. She also advises clients in connection with regulatory compliance involving technology transactions relating to AI, financial services, payment systems and networks, cloud computing, privacy compliance, the management and security of data, digital assets, governance frameworks and intellectual property. Wendy also offers guidance on third-party risk management, business continuity, information security and incident management.

Wendy is recognized for her expertise by numerous industry publications including Chambers Canada and Chambers Global (Technology Band 1), The Canadian Legal Lexpert Directory and the Lexpert/American Lawyer Guide (Technology Transactions; Computer & IT Law), Best Lawyers in Canada (FinTech Practice; Information Technology Law; Privacy and Data Security Law; "Lawyer of the Year", FinTech Practice) and Who's Who Legal (Banking — Fintech; Data — Information Technology; Telecommunications Media & Technology).

  • Canadian Tire Corporation, Limited

    Canadian Tire Corporation, Limited in connection with a seven-year strategic partnership with Microsoft Corporation and Microsoft Canada Inc.

  • BAI Communications

    BAI Communications in the sale of its Canadian business to Rogers Communications

  • TD Bank

    TD Bank in its data access agreement with Yodlee

  • Interac Corp.

    Interac Corp. in Canada's new real-time payments system

    • Several strategic alliances for retail and financial services clients relating to the development, marketing and offering of mobile applications, including mobile banking, mobile wallet and loyalty-related applications
    • Strategic alliance for the distribution of an innovative new mobile POS technology through the merchant payment system network for a major Canadian bank
    • Several strategic alliance for the marketing and operation of credit or debit card-based co-branded and white labelled loyalty programs
    • Several agreements for the development, hosting and operation of a loyalty platform and for loyalty fulfillment services for a major Canadian bank
    • Agreement for the development and support of integrated payment systems for debit, credit and stored value cards for a leading international food retailer
    • Outsourcing of a major customer-facing service offering for key business customers of a major Canadian bank
    • Development, hosting and operation of a trading platform for a major Canadian bank
    • Offshore outsourcing of several back office business processes for a major Canadian bank
    • Development, hosting and support of on-line systems for a regulatory body
    • Development and support of a customer information system for a major Ontario utility
    • Repatriation of a variety of technology and network services for a major Canadian bank
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  • Chambers Canada: Canada’s Leading Lawyers for Business: Recognized in Information Technology (Band 1) (Nationwide)
    • Wendy has a well-earned reputation for being one of the best technology lawyers in Canada. Just getting her in the room can shift the table in our favour. We have leveraged her deep market expertise to take principled stands in negotiations.
  • Chambers Global: The World's Leading Lawyers for Business: Recognized in Information Technology (Band 1)
    • "Wendy is very tough and very smart. We prefer to use her on those high-level matters and sophisticated transactions with high-level parties on the other side."
    • "Sources commend...Wendy Gross for her leading technology expertise and creative approach when advising on technology and outsourcing transactions."
  • The Canadian Legal Lexpert Directory: Recognized in Technology Transactions; Computer & IT Law
  • The Lexpert/American Lawyer Guide to the Leading 500 Lawyers in Canada: Recognized in Computer & IT Law and Technology Transactions
  • Best Lawyers in Canada: Recognized in FinTech Practice; Information Technology Law; Privacy and Data Security Law; Technology Law; "Lawyer of the Year", FinTech Practice (2021)
  • Legal 500: Recognized in Technology Law
  • Who's Who Legal: Recognized in Data - Information Technology; Fintech & Blockchain - Fintech; Fintech & Blockchain - Blockchain, Canada - Data; Canada - Fintech & Blockchain
  • Thomson Reuters: "Stand-out Lawyer"

  • Canadian IT Law Association
  • ITech Law Association
  • Licensing Executives Society
  • Toronto Computer Lawyers Group
  • Ontario Bar Association: Information Technology and E-Commerce, Entertainment, Media and Communications and Privacy Sections

Wendy has spoken extensively on legal issues relating to outsourcing, joint ventures, licensing and other technology transactions, commercialization of intellectual property, privacy, the internet and e-commerce.She is widely published. Her recent articles and presentations include:

  • Cyber Security: Data Residency, Security and Best Practices, Centre for Outsourcing Research and Education, May 28, 2015
  • Mobile Payment Technology Issues, 18th Annual IT Law Association Conference, October 20, 2014.
  • Data Considerations in Payment Ecosystems, 2014 AccessPrivacy Annual Privacy Conference, June 25, 2014
  • Privacy, Security and Ownership of Mobile Payments Data, The 2014 Information Technology Law Spring Forum (presented by IT.Can and The Law Society of Upper Canada), June 16, 2014.
  • Supplier Risk Management: Emerging Trends and Issues, Sourcing Interest Group (SIG), June 9, 2014.
  • Moderator, Outsourcing: Latest Trends and Developments (The Vendors’ Perspective), Toronto Computer Lawyers Group, April 8, 2014
  • Increasing Efficiencies and Reducing Costs by Using Outsourcing Arrangements, Canadian Institute’s 19th Annual Regulatory Investigations for Financial Institutions, 2013
  • Co-Chair, The Seventeenth Annual Canadian IT Law Association Conference, October, 2013
  • Key Issues in Commercial Technology and Outsourcing Arrangements, the 2012 Information Technology Law Spring Training Forum, June 19, 2012