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From hiring seats to onboarding intelligence. Greg Coleshill, Chief Commercial and Operating Officer at vigilant.ai, joins host Jennifer Geary to explore what two decades in talent and recruitment really teaches you about the future of work — and why the smartest leaders are now applying people principles to AI teammates.
In this episode, host Jennifer Geary speaks with Greg Coleshill, whose 18-year career building talent and recruitment businesses across technology and financial services has taken a fascinating pivot. Now as COO at vigilant.ai, Greg is helping regulated organisations deploy AI agents safely, governed, and audit-ready — treating them less like software and more like a new hire.
You'll learn how to:
- Think about AI teammates the way you think about human hires — onboard, collaborate, build trust, then scale.
- Identify the right use cases for AI agents in your organisation, beyond simple automation.
- Navigate the noise of AI vendors and hype to find real business benefit.
- Govern AI agents safely in regulated environments with the right controls and audit trails.
- Design a hybrid workforce structure that blends people and agents effectively.
- Avoid the trap of using AI just to do the same old processes faster.
About Greg Coleshill:
Greg Coleshill is Chief Commercial and Operating Officer at vigilant.ai. He spent nearly 20 years leading businesses delivering innovative talent solutions to technology and financial services firms, including 18 years building and scaling multiple business units at the same organisation, culminating in his appointment as CEO and successfully managing the business through an acquisition and integration event. At vigilant.ai, Greg applies the lessons of two decades managing human capital to the next frontier of organisational growth — helping regulated firms build hybrid workforces of safe, governed, and audit-ready AI teammates.
Chapters:
00:00 — Episode Begins 01:47 — Introducing Greg Coleshill 03:00 — 18 years in recruitment: one business, never standing still 09:54 — The pivot: from talent solutions to AI agents 11:40 — Non-deterministic intelligence — and why it changes everything 13:30 — What C-suite leaders are really struggling with on AI 17:00 — Inside vigilant.ai: the agentic operating system for regulated businesses 22:35 — The AI Chief of Staff: a real-life before and after 27:00 — The mindset shift: onboard, collaborate, trust, then scale 29:00 — Use case: 60%+ time saving in a complaints process within 30 days 32:24 — Org design: structuring people and agents together 34:39 — AI fatigue, slop and hallucinations — navigating the downsides 37:53 — Recommended reading and resources for getting started
Resources & Links:
- C-suite Framework courses & books: https://csuiteframework.co.uk/
- Find out more about vigilant.ai: https://vigilant.ai
- Book: Agentic Artificial Intelligence by Pascal Bornet
- Book: Co-intelligence by Ethan Mollick
- Podcast: The Artificial Intelligence Show
- Podcast: Me, Myself and AI
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