From Startup Grit to Enterprise Scale: The Cask Canada Approach

From Startup Grit to Enterprise Scale: The Cask Canada Approach

Released Monday, 7th July 2025
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From Startup Grit to Enterprise Scale: The Cask Canada Approach

From Startup Grit to Enterprise Scale: The Cask Canada Approach

From Startup Grit to Enterprise Scale: The Cask Canada Approach

From Startup Grit to Enterprise Scale: The Cask Canada Approach

Monday, 7th July 2025
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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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From The Podcast

Startup Builders & Backers is a podcast that takes you inside the minds of the people shaping the future of technology and entrepreneurship. Part of the Tech Talks Network, this series goes beyond headlines and hype to bring you real conversations with startup founders, angel investors, VCs, and seasoned operators who are building, backing, and scaling the next generation of companies.You might know me from Tech Talks Daily, where we explore a broad spectrum of business technology. But here, the focus narrows to the pulse of the startup ecosystem. From the spark of an idea to the complexities of funding, go-to-market strategies, team building, and exits, this series unpacks what it really takes to create a successful venture in today’s fast-moving environment.In each episode, we uncover what motivates founders to leave stability behind in pursuit of something bigger. We explore how investors identify promise amid uncertainty, what they’re looking for right now, and how early-stage bets evolve into long-term partnerships. Along the way, we look at the less polished moments—the pivots, the pressures, and the personal lessons that shape both people and products.Whether you're an aspiring entrepreneur, an investor looking for your next big bet, or a startup operator navigating growth, these conversations offer insight, connection, and an honest look at the reality behind the pitch decks.So what does it take to build something from nothing, and who are the people willing to take that risk? Let’s find out together. And if you’ve got a story to tell or a venture to share, I’d love to hear from you.

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