Alison Kaizer and Andrew D'Souza

Alison Kaizer and Andrew D'Souza

Author: Evan McCann March 30, 2026 Duration: 54:56

This episode explores how AI is transforming hiring practices, emphasizing real-time testing, new roles, and the importance of human intuition in recruitment. Guests Ali and Andrew share insights on leveraging AI for better matchmaking, feedback loops, and building effective, nimble teams.


  • Alison is the Partner, Talent at Golden Ventures
  • Andrew is the Founder of Boardy


Chapters

00:00 Introduction and Focus on Broken Hiring Practices

01:11 Traditional Success Metrics in Hiring Are Changing

01:57 Real-Time Testing and Practical Skills Over Past Experience

02:44 Shift from Filling Roles to Strategic Matchmaking

03:55 New Roles Emerge: AI Adoption Experts and Prompt Engineers

05:48 The Evolving Role of People Management in AI Era

07:20 The Value of Curiosity and Openness to Change

08:50 Technical Skills and Building with Latest Tools

10:22 Accessing Talent Beyond Traditional Platforms

12:02 Deep Conversations and Motivations in Hiring

14:04 Using AI for Better Candidate Matchmaking

17:01 The Power of Personal Connections and Fit

17:23 Feedback Loops and Continuous Improvement in Hiring

21:20 AI as a Central Team Member and Meeting Facilitator

23:48 Scaling Talent Acquisition with AI and Data

29:45 Building Long-Term Relationships and Trust with AI

33:18 The Human Element in AI-Driven Conversations

37:07 Future of Audio and Speech in AI Interactions

42:44 Trust, Accountability, and Outcomes in AI Recruitment

47:37 Balancing AI and Human Judgment in Hiring

52:17 Personal Relationships and Work Dynamics

54:13 Closing Remarks and Key Takeaways



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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