S7E15 - SaaS Monetization in 2026: Tiering, Usage, AI Add-Ons & Pricing Experiments with Krzysztof Szyszkiewicz

SaaS monetization in 2026 is being reshaped by smarter tiering strategies, flexible usage-based models, AI-powered add-ons, and bold pricing experiments that help companies grow revenue while meeting evolving customer expectations. In this episode of the Grow Your B2B SaaS podcast, host Joran speaks with Krzysztof “Chris” Szyszkiewicz, the co-founder of ValueShips, a boutique pricing consultancy that works primarily with technology companies, particularly within SaaS and AI. The conversation, recorded live at the SaaS Summit in Benelux, explores where SaaS pricing is heading in 2026 and how companies can gain an advantage by rethinking monetization, packaging, and expansion strategy.

Chris offers practical insights on output and success-based pricing, the rise of AI add-ons, the importance of structuring tiers based on willingness to pay, and the need to view pricing as a continuous process. He also explains how to run pricing experiments, avoid common traps, and use straightforward frameworks to protect margins, especially in AI-driven products where usage costs can escalate quickly. For any SaaS company preparing for growth in 2026, this discussion provides a grounded and actionable blueprint for building a pricing system that supports scale.

Key Timestamps

• (0:00) – SaaS Pricing in 2026 Is Gonna Get Wild
• (0:53) – Live From SaaS Summit Benelux
• (0:57) – Meet the Pricing Guy Behind ValueShips
• (1:11) – What Will SaaS Pricing Look Like in 2026?
• (1:19) – Expansion Revenue Is the New Growth Hack
• (2:32) – Scale Smarter With Usage Metrics
• (3:45) – Stop Guessing: Do Real WTP Research
• (4:10) – Switching to Hybrid Pricing Without Chaos
• (4:23) – Test AI Add-Ons Before Going All-In
• (5:43) – The New AI-Native SaaS Models
• (5:58) – Freemium Isn’t Free
• (7:08) – Booking.com-Style Pricing Comes to SaaS
• (8:04) – Pricing Is a Process
• (9:44) – Ad Break: Reditus
• (9:57) – A/B Test Your Pricing Like a Pro
• (10:30) – How to Test Pricing on Existing Customers
• (11:38) – The Churn Math You Must Know
• (12:41) – The Most Expensive Pricing Mistakes
• (13:45) – Don’t Blow Up Your Pricing Model for AI
• (14:47) – When Credits Pricing Works
• (15:01) – Keep AI Costs From Killing Margins
• (16:10) – Utility-Style Billing 101
• (16:48) – Early-Stage Pricing to Hit 10K MRR
• (18:15) – Scale to $10M ARR Without Revenue Leaks
• (19:24) – Final Takeaways
• (19:27) – Connect With Chris
• (19:40) – Outro & Subscribe