How AI Is Breaking Traditional Per-User Pricing Models with Craig Wilson

Craig Wilson, Director of Pricing and Packaging at Moody's Analytics, brings extensive experience from major financial services companies including S&P and Experian. Starting his career in financial analysis at a Scottish car retailer after his soccer dreams didn't materialize, Craig discovered his natural strengths in numbers and analytical tools, leading him to specialize in pricing across subscription products, deal desk operations, and information technology services.

In this episode, Craig explores the dual challenge of AI in pricing: how to monetize AI-enhanced products and how to leverage AI tools for pricing decisions. Drawing from his experience at Moody's, he discusses why traditional pricing principles still apply to AI products while acknowledging the fundamental disruption AI creates for per-user models. Craig shares practical insights on using AI as a pricing coach and the critical importance of early involvement in product development.

Why you have to check out today's podcast:

• Learn why AI pricing follows traditional value-based principles but requires new approaches to pricing metrics and value capture.
• Discover practical ways to use AI tools like Microsoft Copilot for pricing strategy, stakeholder communication, and sales enablement.
• Understand the critical timing of pricing involvement in AI product development to influence monetization strategies from the ground up.

"Get involved in the product development process as early as possible, particularly in the era of Gen AI and agentic AI."

– Craig Wilson

Topics Covered:

01:30 — Craig's pricing journey: From Scottish car retailer to Moody's Analytics pricing leader

04:15 — Why AI pricing fundamentals haven't changed: Still about value creation and capture

06:30 — The consensus problem: No clear patterns yet in AI pricing

08:45 — Use case example: using AI to do pricing

11:15 — Using AI as a pricing coach: Daily conversations with Microsoft Copilot for strategy development

14:30 — Communication enhancement: Translating pricing concepts for different business personas

16:45 — Sales enablement evolution: AI-powered guidance for complex solution positioning

19:20 — Trust and validation concerns: The information vs. agentic AI distinction

21:45 — Economic value estimation: How AI can finally make this pricing holy grail practical 23:30 — The monetization investment gap: Companies building AI capabilities without pricing strategies

Key Takeaways:

On Early Involvement in Product Development:

"Get involved in the product development process as early as possible, particularly in the era of Gen AI and agentic AI." – Craig Wilson

On Per-User Pricing's Death:

"In the world of particularly agentic AI solutions, the per-user model is becoming obsolete. I can't see a place for it." – Craig Wilson

Resources and People Mentioned:

• Moody's Analytics: https://www.moodysanalytics.com/
• Tom Nagle: "Strategy and Tactics of Pricing" book: https://www.taylorfrancis.com/books/mono/10.4324/9781315266220/strategy-tactics-pricing-thomas-nagle-john-hogan-joseph-zale
• Steven Forth: https://www.linkedin.com/in/stevenforth/
• Kyle Poyar: https://www.linkedin.com/in/kyle-poyar/
• Stuart Wintertere: LinkedIn thought leader on AI value
• Microsoft Copilot: Daily AI coaching tool

Connect with Craig Wilson:

• LinkedIn: https://www.linkedin.com/in/craig-wilson-5857ba4a/
• Email: craig.wilson@moodys.com

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: mark@impactpricing.com