Why AI Gets Pricing Wrong and How to Train It to Get Pricing Right with Roberto Rivera

Roberto Rivera is the founder of Pricing Nerd, where he builds AI-powered pricing workflows for B2B companies. With more than 25 years in pricing and experience working alongside some of the field's early pioneers, Roberto has focused on turning pricing expertise into scalable AI-powered workflows.

In this episode, Roberto explains why simply asking AI "What price should I charge?" produces unreliable answers. AI needs more than business data. It needs the context and pricing skills required to interpret that information correctly.

Why You Have to Check Out Today's Podcast:

• Learn why AI needs pricing skills and business context, not just more data, before it can produce useful price guidance.
• Discover how to make AI pricing recommendations more trustworthy and defensible using deterministic methods, formulas, and supporting evidence.
• See how AI can help uncover hidden value and margin leakage, from customer value modeling to forgotten contract clauses.

"AI can compile all that information... but at the end of the day, the human and the situation they're in, they're going to go with their best judgment." — Roberto Rivera

Topics Covered:

01:30 – From Pricing Consultant to AI-Powered Pricing. Discover how Roberto's 25+ years in pricing led him to build AI-powered workflows designed to help B2B companies turn value into margin at scale.

04:00 – Why AI Gets Pricing Wrong. Learn why asking AI "What price should I charge?" isn't enough — it needs deep business context and a clear understanding of what pricing actually means inside your organization.

06:00 – Context Isn't Enough: AI Needs Pricing Skills. Roberto introduces the second critical ingredient for AI-powered pricing: skills that teach AI how to interpret business information and apply pricing frameworks.

08:30 – The 48 Pricing Skills AI Can Learn. Explore Roberto's concept of pricing skills, from value-based pricing and willingness to pay to customer value modeling and contract analysis.

11:00 – Where AI Stops and Human Judgment Begins. Learn why AI can process pricing frameworks and massive amounts of information, but humans still need to weigh relationships, politics, sensitivities, risks, and accountability.

19:00 – What Happens When Humans Override the AI? Learn how AI can turn pricing overrides into a learning system, using previous adjustments to improve future recommendations.

21:00 – AI as the Smart New Hire for Your Pricing Team. See how AI can combine information from marketing, CRM, ERP, contracts, and customer data to create a defensible pricing recommendation and help less-experienced sellers learn.

26:30 – Don't Wait for Perfect Data. Start With One Painful Problem. Roberto's advice for getting started with AI: don't try to "boil the ocean." Pick one painful, repetitive pricing problem and use AI to solve it.

29:30 – Roberto's Final Pricing Advice: Just Start. Why messy data, complex businesses, and internal politics shouldn't stop companies from experimenting with AI.

Key Takeaways:

"Skills are a massive component of giving the AI the power to not only know about your business, but interpret your business in a way that's going to produce good and solid price guidance." — Roberto Rivera

"The beautiful thing that we have, Mark, is that we've been in the space for 25, 30 years... and we know what good looks like." — Roberto Rivera

"You don't let perfection kind of limit what you think you can do and just begin to experiment and go for it." — Roberto Rivera

Connect with Roberto Rivera:

• Email: roberto@pricingnerd.com
• Website: https://www.pricingnerd.com/
• LinkedIn: https://www.linkedin.com/in/robertorivera-pricing/
• Book: AI for B2B Pricing: Turning Value into Margin at Scale

Connect with Mark Stiving:

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