Shreya Gupta is Director, Legal Counsel (Technology, AI, and Privacy) at Loblaw Companies Limited. She was previously an Associate at Norton Rose Fulbright, where she maintained a technology-focused practice and served as Co-Chair of the firm’s Race Equity Council. Ms. Gupta has extensive experience advising on technology contracting, AI governance, cybersecurity, and privacy compliance, working closely with business teams to navigate complex regulatory and commercial landscapes. Beyond her corporate practice, Ms. Gupta is passionate about emerging technologies and their legal implications, particularly in AI-driven solutions and data protection. In an interview with Windsor Law student and LTEC Lab Research Assistant Christina Lee, she shares insights on her career journey, the evolving landscape of technology law, and her experiences at Windsor Law.
Interview with Shreya Gupta: Navigating Technology, AI, and Privacy Law
Q: Can you tell us about your journey from Windsor Law to your current role as Director, Legal Counsel at Loblaw Companies?I began my career in the tech industry before law school, where I gained valuable exposure to startups and entrepreneurs. This experience shaped my understanding of the business and technological challenges that companies face. During law school, I summered at Norton Rose Fulbright, where I worked closely with startup companies and focused on technology contracts. My interest in technology contracting started there, and I continued to hone this focus throughout my articling experience. This eventually led me to specialize in technology, privacy, cybersecurity, and AI law, which I now practice as Director, Legal Counsel at Loblaw Companies.
Q: What are some unique features of your current role as Director, Legal Counsel?In my role, I provide legal guidance on emerging technologies and work to simplify complex issues, offering practical solutions to the business. My technology law practice can be broken down into a couple key pillars. One pillar is privacy and data protection, where I advise the business on privacy and cybersecurity-related matters and negotiate contracts with privacy considerations. Another pillar is technology contracting & AI governance, which involves negotiating with technology vendors, establishing AI governance policies, and conducting due diligence on AI usage. AI is just another technological advancement, and like any tech product, it requires careful management. As in-house counsel, I collaborate directly with business teams to develop practical solutions that align with legal and ethical standards.
Q: How did your interest in technology, AI, and privacy law develop over time?I’ve always had an interest in law, but my fascination with technology grew after graduating from Ivey Business School. While I was working at a design studio in Toronto, I met a group of passionate individuals with whom I eventually established a global non-profit focused on innovation in healthcare. During those few years, I worked closely with entrepreneurs and really connected with the tech industry. I firmly believe that today, every company is a technology company. No matter the legal field one practices in, or whether they are in private practice or in-house, technology plays an important role and legal professionals must understand the associated risks.
Q: What challenges did you face in entering the field of technology law, and how did you overcome them?When I first entered the field, I didn’t have a technical background, which could have been a challenge. I learned some beginner-level coding as a hobby—not to become an expert, but to gain a foundational understanding of how technology works. I made it a habit to stay updated on technological advancements, study industry frameworks and regulations, and ask lots of questions. The other challenge is that technology is always evolving. Legal professionals must be adaptable in this space, and I embraced this by constantly learning and improving my knowledge.
Q: What are some challenges you’re currently facing in your role, and how do you navigate them?The rapid pace of technological change remains one of my biggest challenges. I work in a fast-evolving space, where staying ahead of trends and anticipating potential risks are critical. One of my main roles is bridging the gap between legal, business, and tech teams. I make sure that all stakeholders understand the risks and opportunities new technologies bring and collaborate to find solutions that work for everyone.
Q: What advice would you give to law students interested in technology and privacy law?I would advise law students to stay engaged with technological changes because technology is not going away. I recommend reading widely and following thought leaders on LinkedIn who break down complex topics using flowcharts and practical insights. Networking with professionals in the field and reading through the various examples of vendor terms that are available online can be hugely helpful. I also suggest listening to tech and privacy law podcasts to gain a broader perspective on the industry. By staying informed and continuously learning, students can position themselves for success in the ever-evolving field of technology law.
Q: What are the key legal challenges associated with the use of AI?
In many cases, challenges associated with the use of AI are similar to the use of any other form of technology – for example, we need to think about what’s happening with the data, consider privacy implications and ensure appropriate security controls are in place. With generative AI specifically, given it’s a “black box” to some degree, ensuring transparency while addressing risks such as bias becomes increasingly important. The other challenge is change management – widespread use of AI (and specifically, generative AI) is a major shift in how technology is leveraged, and successful and responsible use requires buy-in from all stakeholders. As businesses increasingly adopt generative AI, the benefits include enhanced efficiency and automation, however, risks associated with the specific use case will need to be considered and mitigated. I like to think of AI as a child – we should think about what we’re asking the child to do, what information we’re sharing with the child and whether we can, without question, rely on what the child is telling us.
Q. What is your favourite memory at Windsor?One of my favourite memories from Windsor Law is participating in the Bowman Tax Moot and learning from Justice Aroca. I also really enjoyed working with Dean Waters at the time as the SLS President, where I had the opportunity to help recruit professors and engage with the student body as well as the faculty. The experience taught me a lot about leadership and collaboration. The "work hard, play hard" mentality at Windsor Law really stood out to me as well—I made sure to dive into academics and extra-curriculars while also taking time to enjoy social events and connect with my peers.
Q. What has been the difference being in private practice vs in house?
There’s a common myth that in-house legal practice is a 9-5 job and “easier” than private practice, but the reality is that workload can be just as heavy (if not more). It really depends on the company and the role. Having said that, the nature of the work does differ - in-house lawyers often work across a variety of issues and in collaboration with multiple stakeholders, which can require significant effort and coordination. The part I’ve found exciting is being able to see the direct impact of my advice, which wasn’t always clear in private practice. The key takeaway here is that you should choose a career path that aligns with your interests and goals at the time, including the skills and experiences you’re looking to gather. What truly matters is finding a role that excites you, whether it's in-house or in private practice, and pursuing it with passion and dedication.
Authored By: Christina Lee
