In the procurement world, the real danger is often failing to obtain the goods and services that keep public programs running, not whether every procedural box has been ticked, says Rosslyn Young. “Oftentimes, not getting the service or the goods you need... can be a bigger risk than the legal risk that you are trying to mitigate or eliminate,” she says.
Young, who recently joined Supply Ontario as chief legal officer, has built her career around public procurement and is candid about how the system can fail the organizations it is meant to serve. Early in her private practice, acting for school boards, she saw how publicly funded bodies “have to comply with all the rules of public procurement” and how layers of regulation can divert attention away from what a vendor is delivering, she says. That experience led to a role at Ontario Realty Corporation on a major managed services deal, followed by a boutique that specialized in acting only for purchasers across Canada.
Across those files, the legal framework was shared, but the practical problems varied significantly across industries. While having a transparent framework was a laudable goal, “the layering of regulations and rules makes it so complex that ultimately, sometimes the focus becomes on the process of identifying a vendor, instead of what that vendor is bringing through the door,” she says. That realization – that procurement can lose sight of outcomes when process dominates – has shaped every role that followed, including senior positions at the LCBO, Metrolinx and now Supply Ontario.
The most consequential choice in her career was to step away from legal practice and take on business leadership of procurement at the LCBO and then Metrolinx. That shift forced her to manage budgets, own a P&L, lead teams and influence across the organization.
When she was asked to return to the LCBO as chief legal officer, Young could combine that business grounding with legal training. As she puts it, “the more you move up, the less law you do... and your business involvement goes up.” Success at senior levels, she says, depends on using law as a tool to manage risk and enable strategy rather than as an end in itself.
That mindset drove changes to how legal and procurement worked together. Young assigned specific lawyers as ambassadors to different client groups, not to hoard files but to sit at leadership tables, surface challenges and become escalation points. The goal was to understand commercial and operational pressure points well enough to balance them against legal risk, rather than reflexively shutting down anything that made lawyers nervous. A fear of challenge often paralyzes public procurement culture, and she has tried to build a sharper understanding of what risk really matters, because the drive to eliminate legal exposure can starve frontline programs of the goods and services they depend on, she says.
She is equally direct about the futility of sending every contract to the legal department. When she started at the LCBO, “every single contract in the organization had to come to the legal department,” a setup she describes as “brutal” because low-value agreements crowded out the complex files that warranted real legal attention. Her answer was to segment the contract landscape, push lower-risk work back to the business with templates and tools, and reserve scarce legal time for high-impact, high-risk transactions, she says.
Young has also adopted a more open approach to engagement with bidders in major procurements. She points to a large LCBO project where the team ran an extended dialogue process with multiple proponents. Traditional models insisted that everything be managed through rigid written RFPs and formal Q&As, limiting the ability to probe assumptions and shape a better deal. By contrast, a competitive dialogue allowed an “ongoing conversation with multiple bidders” and recognized that vendors “are different companies, bringing potentially different solutions,” she says.
Today, Young is about six months into her role at Supply Ontario, which is consolidating purchasing power across the provincial and broader public sectors while securing key stockpiles, she says. The organization is still relatively small, with a mandate that spans a reliable domestic supply chain for PPE and other medical commodities, as well as aggregating purchases for everyday items such as laptops, mobile devices, and software licences.
The idea is not to strip individual agencies of control over strategic contracts, such as logistics arrangements that are central to the LCBO’s business model, but to free their procurement teams to focus on those core deals while Supply Ontario handles shared, commoditized spends. That, Young says, means focusing on areas where there is real commonality and purchasing power, and ensuring the resulting contracts are “as easy as possible to use” so clients can access savings without new administrative headaches.
Making that model work requires more than legal drafting. Young emphasizes the importance of building political capital by clearly explaining Supply Ontario’s role to decisionmakers and then delivering agreements that are seamless and frictionless for front-line users. Her priorities are to identify consolidation opportunities and ensure internal client groups can concentrate on projects that drive their mandates rather than wrestling with boilerplate, she says.
Young is candid about the imposter syndrome that has followed her into successive leadership roles, but she pushes younger lawyers to focus on why they are being hired. They are brought in not because anyone expects them to know every answer, but because they are “smart enough to figure out the problem” and have the training to work through novel issues, she says. For those willing to think like businesspeople and stay focused on the real risks to the programs they support, public procurement offers a demanding, high-impact legal career.