Wendy Gross

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).


Representative Work

  • 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

    Latest Insights

    • Osler Update May 2, 2024

      OSFI to finalize risk management guidance covering the use of AI and machine learning within models

      The OSFI is releasing an updated guidance on model risk management for financial institutions.

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      OSFI to finalize risk management guidance covering the use of AI and machine learning within models
    • Webinar May 10, 2023

      2nd Annual Payments Seminar: Spotlight on the RPAA

      View Osler’s Payments Law update where our panel of legal experts bring their perspectives on what businesses need to know – and how they can...

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      2nd Annual Payments Seminar: Spotlight on the RPAA
    • Webinar Mar 7, 2023

      Osler AI series: A primer on the technology, common and emerging uses, opportunities and challenges

      Join us as we bring together AI experts from Osler and across industry to explore and better understand the power of AI and its impact on us all.

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      Osler AI series: A primer on the technology, common and emerging uses, opportunities and challenges
    • Osler Update Apr 28, 2022

      Evolution of Canada’s payments ecosystem picking up speed (webinar)

      Canada’s increasingly complex and ever-evolving payments ecosystem is driving new considerations for businesses.

      Read more
    View all Insights

    Awards and Recognition

    • 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”

    Media Mentions

    • Osler News Feb 16, 2024

      Osler recognized as a leading firm in Chambers Global 2024 Guide

      Osler recognized as a leading firm in Chambers Global 2024 Guide

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    • Osler News Jan 9, 2024

      34 Osler lawyers recognized in 2024 Lexpert/American Lawyer Guide to Leading 500 Lawyers in Canada

      Osler is pleased to announce that 34 of our lawyers have been recognized in the 2024 edition of the Lexpert/American Lawyer Guide to the Leading 500...

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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 Feb 16, 2023

      Osler recognized as a leading firm in Chambers Global 2023 Guide

      We are excited to announce that we have once again been recognized as a leading firm in the Chambers Global 2023 Guide.

      Read more
    View all

    Community Involvement

    • Perimeter Institute, Board Member

    Speaking and Writing

    Speaking Engagements

    speaker 10/5/2023
    2nd Annual Payments Seminar: Spotlight on the RPAA
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    speaker 07/3/2023
    Osler AI series: A primer on the technology, common and emerging uses, opportunities and challenges
    Read more
    speaker 28/4/2022
    Payments Law in Canada – An important update for all businesses
    Read more
    speaker 07/10/2021
    Disruption in the Supply Chain and Distribution Ecosystem – Osler and Special Guests Discuss Lessons Learned and What’s Next
    Read more
    speaker 30/9/2020
    Hot Topics in Canadian Commercial Leasing and Retail
    Read more
    speaker 28/10/2019
    2019 CAN-TECH Annual Conference
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    speaker 27/1/2019
    Unlocking AI: Overcoming the legal and ethical challenges
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    speaker 26/4/2016
    Technology Procurement Workshop – How Your Strategic Choices Affect Your Results
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    speaker 24/2/2016
    Outsourcing for Financial Institutions – Practical Strategies for Complying with OSFI B-10
    Read more

    Published Work

    • 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

    Credentials

    Education

    • University of Toronto, J.D.
    • University of Toronto, B.Sc. (Hons.) (Computer Science)

    Languages

    • English

    Professional Affiliations

    • 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