Organized Chaos

episode artwork

Nahed Khairallah

02 December 2025

34m 6s

Ep. 35 - The New HR Frontier

00:00

34:06

In this episode of Organized Chaos, I am joined by Gwenevere Crary, founder of Guide to HR and host of the "Scaling with People" podcast. Gwenevere is a strategic visionary in the HR world and she shares her forward-thinking approach to AI-enabled HR strategies and the unique challenges startups face as they scale.

Key Topics Discussed

  • Guinevere's Journey to HR: From a background in actuarial mathematics to leading people operations in high-growth startups.
  • AI Enablement in HR: How to leverage AI to automate tasks you hate and augment your own skills, whether in writing or data analysis.
  • The Future of HR with AI: A look at advanced AI applications, including a 24/7 AI coach for managers that facilitates role-playing for difficult conversations and tracks employee development goals.
  • New Skills for HR Professionals: The need for HR leaders to possess deep business acumen, understand company financials, and think like a business operator. The traditional, admin-heavy HR role is obsolete.
  • Challenges in Scaling Startups: Advice for HR professionals on how to gain credibility, present themselves as strategic partners, and build crucial relationships with leadership.
  • HR's Role in Owning Technology: Why HR is positioned to own AI implementation, ensuring its use is safe, unbiased, and effective for the entire organization.
  • The Hard Truth: Knowing when to leave a role if you no longer have the trust and alignment with leadership to be effective.

Links

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