Roger Kirkness from Convictional

Roger Kirkness from Convictional

Author: Evan McCann April 24, 2025 Duration: 50:51

Roger Kirkness is the Founder and CEO of Convictional.


Convictional is the infrastructure that powers decisions at the world's most ambitious companies.


Takeaways

- The Value of Y Combinator Programs

- Modern Dropship Acquisition and Company Pivot

- Ask The Question: What Happens if it Works?

- Tobi's AI Memo

- AI in the Workplace: Opportunities and Challenges

- CEOs Using ChatGPT and Claude to Make Decisions

- Bias in Companies

- Navigating AI's Future in Organizations

- Leadership in the Age of AI

- Cross-Functional AI Adoption in Companies

- The Impact of AI on Company Structures

- Choosing to Build in Waterloo

- Remote Work: Strategies for Success

- Dogfooding Your Own Product


Chapters

00:00 The Value of Y Combinator Programs

04:12 Founding the Company: Genesis and Growth

08:59 Navigating Acquisitions and Market Challenges

11:41 Business Operations and Knowledge Management

16:14 AI in the Workplace: Opportunities and Challenges

21:08 Decision-Making in Startups and Beyond

25:59 Navigating AI's Future in Organizations

28:19 The Role of Essays in Shaping AI Perspectives

30:40 Leadership in the Age of AI

33:29 Cross-Functional AI Adoption in Companies

37:47 The Impact of AI on Company Structures

41:06 Remote Work: Strategies for Success

45:14 Dogfooding: Using Your Own Product

47:00 Resilience in Entrepreneurship


Keywords

Y Combinator, startup programs, business operations, AI in workplace, decision making, entrepreneurship, knowledge management, acquisitions, B2B e-commerce, Convictional, AI, leadership, organizational change, remote work, cross-functional collaboration, dogfooding, entrepreneurship, company structure, management philosophy, technology adoption


Evan McCann sits down with the people shaping Canada's business landscape, moving past the polished success stories to get into the real work that happens behind the scenes. The Hard Part with Evan McCann is built on conversations with founders, investors, and leaders who have navigated unique challenges, focusing on the pivotal decisions and often overlooked struggles that define a venture. This podcast explores the specific strategies and personal playbooks that have driven impact, offering a rare look at the operational truths of building something significant. While the spotlight frequently falls on innovators elsewhere, these episodes are dedicated to the Canadian visionaries whose work is redefining global entrepreneurship from here at home. You'll hear candid reflections on risk, resilience, and the moments that tested their conviction, providing not just inspiration but tangible insight into the mechanics of leadership and growth. Each discussion aims to unpack the nuance of achievement, making it an essential listen for anyone curious about the substance behind the headlines in the Canadian business world.
Author: Language: en-ca Episodes: 100

The Hard Part with Evan McCann
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