The Success Revenue Podcast

Are you under pressure to move on AI - but unsure whether your organisation is actually ready to do it right?

Greg Coleshill spent 18 years scaling human capital businesses, ultimately serving as CEO through a major acquisition and integration. Today, as Chief Commercial & Operating Officer at Vigilant AI, he sits at an unusual intersection: two decades of understanding how people work, applied directly to the challenge of building governed, audit-ready AI teammates inside regulated firms.

This conversation cuts through the noise. Greg brings a perspective most AI voices can't - one built from managing real operational complexity, not just technology.

You'll leave with a clearer sense of how to move from AI curiosity to AI execution, without abandoning the judgment and experience that got you here.

You'll learn:

  • Why most AI initiatives stall at the adoption stage - and why it's an operational problem, not a technology one
  • The signals that reveal whether a business is truly AI-ready, regardless of what leadership says in the room
  • Why your most experienced operators are your biggest advantage in an AI transition - and how to unlock that without turning them into prompt engineers
  • How real-time guardrails change the transformation timeline - and what that means for how regulated firms can finally move from pilot to production
  • Why doing nothing is now a strategic risk - and how to frame AI adoption in terms your teams, your compliance function, and your board can all get behind
  • (00:00) - The Future of AI & Business Transformation
  • (03:14) - Journey & Insights
  • (05:55) - Assessing Organizational AI Readiness
  • (09:08) - AI Protection in Regulated Industries
  • (11:56) - Strategies for Building Trust in AI
  • (15:10) - Overcoming AI Adoption Challenges
  • (18:02) - How AI is Changing Leadership Roles
  • (20:59) - Navigating AI Fear & Uncertainty
  • (24:10) - Advice for Financial Services Operators
  • (26:56) - The Workforce Dynamics Shift
  • (29:46) - Mental Models for Success
  • (33:05) - Rapid Fire Round

Follow Greg Coleshill. 

This episode was brought to you by RevSetter & Nebelus AI.

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Hosts: 

Haydar - LinkedIn 
Ivy - LinkedIn 

Creators and Guests

Host
Haydar Al-Saad
Haydar Al-Saad is the founder and CEO of RevSetter, the Customer Success & Revenue platform that turns CS into the new revenue engine. With almost two decades of experience in building and leading customer-centric teams & organizations, I have a passion for helping companies and teams unlock the potential of every customer in order to improve retention, accelerate expansion, and fuel revenue growth.
Host
Ivy Forero

What is The Success Revenue Podcast?

The Success Revenue Podcast is a human-led, AI-powered show exploring how leaders use AI to drive business results while keeping human impact at the center. Hosted by Haydar Al-Saad and Ivy Forero, the podcast features conversations with founders, executives, and operators from around the globe who are building the future of business with AI.