Borderless AI’s Make It Click podcast is putting Canadian technology leaders in conversation about the moments, decisions, and patterns that shape enduring companies.
In Episode 4, host Willson Cross sits down with two of Canada’s most notable tech builders: Jack Newton, co-founder and CEO of Clio, and Dennis Pilarinos, founder and CEO of Unblocked.
The 70-minute conversation covers the “sliding door” moments that define startups, the role of artificial intelligence in legal and developer tooling, and what it takes to build companies for the long haul.
Newton’s story is one of Canada’s most successful software journeys. He co-founded Clio in 2008 after studying computer science at the University of Alberta and has spent nearly two decades building the company into what Borderless AI describes as the operating system for the legal industry, with more than $500 million in annual recurring revenue and a $5 billion valuation.
Pilarinos brings a different but equally compelling perspective. After spending nine years at Microsoft helping build Azure, he became Amazon’s first employee in Vancouver. He later built Buddybuild, which was acquired by Apple, and is now leading Unblocked, a company focused on giving developers and AI agents access to institutional knowledge.
Together, Newton and Pilarinos offer a candid look at the founder mindset, from managing a cap table over decades to building context engines that can create meaningful competitive advantages. The episode also explores why AI is moving quickly through both legal technology and developer tools, two sectors where access to accurate context, institutional memory, and workflow intelligence can materially change how work gets done.
For employers, founders, and talent leaders, the episode offers a useful window into how high-growth companies are built over time. It is not just a conversation about venture capital, exits, or artificial intelligence. It is also about persistence, timing, technical conviction, and the human side of building teams through multiple stages of growth.
The discussion also fits naturally with Borderless AI’s broader focus on the future of work. As companies rethink how they hire, manage, and support global teams, Make It Click highlights the founders and operators who are shaping the next generation of technology companies.
Watch the full episode of Make It Click below.
Borderless AI is a sponsor of Techtalent.ca. Through its Make It Click series, the company is spotlighting conversations with technology leaders about company building, talent, AI, and the future of work.