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From Startup Grit to Enterprise Scale: The Cask Canada Approach

From Startup Grit to Enterprise Scale: The Cask Canada Approach

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In this episode of Startup Builders & Backers, we sit down with Jeff Butler, General Manager of Cask Canada, for a candid conversation on what it really takes to launch and grow a high-performing tech consultancy in today's evolving enterprise landscape. In just over a year, Jeff helped Cask Canada scale to 25 employees and win 11 major clients, all while navigating a crowded implementation partner market, the complexity of ServiceNow, and the growing expectations of Canadian enterprises.

We explore how authenticity, trust, and relentless focus on value have been key to Cask’s success. Jeff reflects on lessons from the dot-com era, the power of genuine client relationships, and why every implementation is more about outcomes than technology alone.

From the rise of AI-enhanced platforms to growing demand for local partnerships, we cover emerging trends reshaping the ServiceNow ecosystem. Jeff also discusses the increasing role of automation, the future of implementation services, and why the best consultants push back instead of simply checking boxes.

If you're building in the enterprise tech space, thinking about platform partnerships, or just want to understand what it takes to lead with heart in a technical world, this episode is for you.

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