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Why long‑term thinking, strong relationships, and showing up at every stage matter for founders and investors in the prairies
Saskatchewan’s startup and entrepreneurial ecosystem continues to grow and attract interest from founders across the province and beyond. From technology startups in their earliest stages to businesses preparing for their next round of growth, the region offers an environment where innovation is increasingly rooted in community. Supporting that growth requires legal advice that reflects how startups are built, through people, relationships, and long‑term decisions.
Joseph A. Gill (Joe), a partner at McKercher LLP, has spent more than a decade working alongside startup founders in Canada as they navigate every moment. His practice focuses on technology, capital raising, and tax law, with a particular emphasis on high‑growth startups across Saskatchewan and the Prairies. Over time, his work has been shaped by deep involvement in the local startup ecosystem and a commitment to supporting businesses from formation through scale.
At the core of Joe’s approach is an understanding that startups are built on relationships. Every company relies on a network of relationships with co‑founders, employees, investors, customers, and collaborators. Those relationships begin with legal agreements that define responsibility, alignment, and trust.
“Every key relationship in your startup, whether co‑founders, employees, investors, customers, collaborators, starts and ends with a document that sets out the terms of the relationship.”
As startups grow, Joe emphasizes that these documents should not remain static. They must evolve alongside the business and reflect how goals, obligations, and risk change over time. Thoughtful legal structure allows relationships to mature without becoming barriers to growth.
Joe’s work often focuses on helping founders think beyond the decision immediately in front of them. Legal choices rarely exist in isolation, especially in high‑growth environments. Decisions made early can ripple forward, shaping future investment, governance, and partnerships.
“It is rarely the case that a decision made today has no ripple effects in the future.”
This perspective becomes particularly important during negotiations with investors and strategic partners. Short‑term wins achieved through aggressive positioning can introduce friction that resurfaces later, sometimes when a business can least afford it. Joe’s role is often to help founders understand how today’s decisions may affect tomorrow’s relationships and to choose paths that support long‑term stability.
Effective legal support for startups also requires an integrated approach. The issues founders face rarely fall neatly into a single category. A single challenge may touch tax planning, privacy compliance, employment structure, and corporate governance all at once.
“Issues are always multi‑faceted and multi‑disciplinary.”
By working collaboratively across McKercher LLP, Joe helps pull together different areas of expertise and translate them into clear, practical actions that founders can deploy immediately. This approach aligns with how startups operate in practice, moving quickly and needing advice that is both strategic and usable.
What continues to motivate Joe’s work is the opportunity to support builders as they create something new. Startups require resilience, adaptability, and a willingness to take risks without guaranteed outcomes. Joe views his role as a supporting one, helping founders navigate complexity so they can focus on building.
“We play a supporting role in a grander story of daring greatly, with the founder as the hero.”
Joe’s commitment to Saskatchewan’s startup community was recognized nationally when he was named a 2025 Lexpert Rising Star - Leading Lawyer Under 40 in Canada. For him, the recognition reflects an approach to law that aligns with an entrepreneurial mindset and close attention to the founder journey.
“This award signifies to me that you can make a significant impact by helping people in the beginning of their journey and hanging on for the ride.”
As Saskatchewan’s innovation economy continues to evolve, the need for legal advice grounded in long‑term thinking remains critical. Through a relationship‑focused, collaborative approach, Joe Gill’s work reflects how legal counsel can support both individual businesses and the broader community they help build. Visit his profile to learn more.
In the video below, Joe shares more about his perspective on working with founders and supporting Saskatchewan’s startup ecosystem.
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