S7E21 - How AI Will Rewrite SaaS GTM in 2026: Pricing, Efficiency & Sales Automation with Jacco van der Kooij

Dec 16, 2025

Jacco van der Kooij, founder of Winning by Design, dives into the future of B2B SaaS and AI. He discusses how real-time user data will be crucial for competitive advantage by 2026. Jacco explores the challenges of usage-based pricing versus subscriptions and warns against pitfalls in freemium models. He emphasizes that while AI will automate many sales tasks, human expertise remains vital. Furthermore, he advocates leveraging user insights for advocacy-driven growth and stresses the importance of aligning teams across functions for success.

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INSIGHT

Real-Time User Data Wins

Real-time, user-level data becomes the defining competitive advantage for AI-native SaaS.
Tracking cohort and single-user usage reveals who will upgrade and where value is delivered.

INSIGHT

Users Become Buyers

AI-native products turn typical buyers into daily users who become champions.
This user-led dynamic accelerates growth compared with traditional logo-focused SaaS sales.

ADVICE

Use Consumption Pricing Sparingly

Avoid relying solely on usage-based pricing as you scale because churn risk and revenue unpredictability grow.
Use consumption pricing selectively and combine it with subscription commitments for stability.

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In this episode of the Grow Your B2B SaaS podcast, host Joran welcomes back Jacco van der Kooij, founder of Winning by Design, to unpack how AI-native SaaS companies are changing the rules of growth, pricing, and go-to-market in 2026. The conversation covers why real-time user-level data is becoming the defining competitive advantage, the pitfalls and promise of usage-based pricing for AI products, the existential challenge of inference costs for freemium models, and the enduring importance of subscriptions with smart hybrid elements. It also dives into how AI will replace the majority of sales tasks, the 30 percent of human expertise that remains essential, and why advocacy and community-driven growth loops will shape pipeline generation. From early-stage foundations to scaling to $10 million ARR, Jacco breaks down what founders need to get right now to thrive in the years ahead.

Key Timecodes

(0:00) - B2B SaaS podcast intro, AI native SaaS, pricing, GTM strategy 2026
(1:01) - Jacco van der Kooij intro, Winning by Design
(1:14) - 2026 success factors: real-time data, PLG, cohort analytics
(2:31) - AI native buyer journey, user-led growth, usage patterns
(3:48) - SaaS pricing: usage-based vs subscription, outcome-based pricing
(4:23) - AI inference costs, freemium risk, monetization challenges
(5:05) - Freemium in AI tools, limits, value gating
(5:23) - Consumption-based pricing vs subscription, hybrid pricing
(6:12) - Hybrid pricing example, membership + per-resolution fees
(7:03) - Efficient growth, GTM efficiency, LTV:CAC, retention, outcomes
(8:36) - AI for customer insights, demand gen, lookalike users
(9:36) - Ad: B2B SaaS affiliate referral platform, AI-powered recruitment
(9:47) - AI and jobs: replace vs enable, workforce impact
(11:19) - GTM with AI: 70% sales tasks automated, CRM, scheduling, summaries
(12:56) - Trust, human expertise, advocacy, risk mitigation
(13:59) - Rebuilding GTM 2026: automation, expert touchpoints, events
(15:00) - Growth loop: usage patterns, word of mouth, advocacy pipeline
(16:26) - Community-led growth: user conferences, LinkedIn sharing, Clay example
(17:02) - SDR strategy: activate users, customer success advocacy
(17:11) - Early-stage advice: real-time data system, analytics
(17:25) - Data stack recommendation: Snowflake, realtime data lake
(17:32) - Scaling to $10M ARR: team alignment, closed-loop GTM
(18:04) - Shared system understanding: recurring revenue, training
(19:01) - Growth Institute by Winning by Design: courses, community, case studies
(19:39) - Where to find: winningbydesign.com, Growth Institute
(19:45) - Closing thoughts, optimism, AI era
(19:54) - Outro: like, subscribe, sponsor, guest/topic requests
(20:17) - Reditus mention, B2B SaaS affiliate program