Jonathan Hansing — Wallabi | How to Go AI-Native: The J-Curve, 10,000 Prompts, and What "Sprinkling AI" Really Signals

Jonathan Hansing is the co-founder of Wallabi, a data, technology, and AI strategy firm helping growth-oriented mid-market companies go AI-native. His team works with CEOs, COOs, and CIOs who feel the pressure to do something with AI — but need a clear path from experimentation to execution. This conversation is full of sharp frameworks and hard-won patterns from the field.You'll Learn:Why "sprinkling AI" is simultaneously a signal of opportunity and a warning sign — and how to tell the differenceHow to assess whether a leadership team actually has the appetite for real AI transformation (not just the desire for it)What the J-curve of technology adoption means for AI specifically — and why Jonathan believes companies have about two years to get on the right side of itThe difference between a company that uses AI and one that is genuinely AI-native — and the single most important shift in mindset that separates themA detailed case study: how a media and events company's request for an email automation workflow revealed — layer by layer — a need for full data architecture overhaul, delivered in 8 weeksChapters:00:00 – Intro00:37 – What Jonathan hopes listeners take away: 10,000 prompts is the new 10,000 hours02:16 – Who is Jonathan Hansing / what is Wallabi04:00 – The Wallabi platform: forward-deployed coaches backed by AI06:30 – A machine learning case study: 18-month problem solved in a week07:03 – The journey: West Point → Army → Narrative Science → Salesforce → Wallabi10:08 – "Sprinkling AI": green flag and red flag12:35 – How Wallabi assesses appetite: the 2-week sprint approach17:03 – Data philosophy: use case first, architecture second18:20 – What's happening beneath the surface for pressured CEOs20:48 – The J-curve: from 20 years to 2 years25:03 – Dual Transformation: managing two change curves at once25:49 – AI-native vs. companies that use AI28:00 – Case study: media & events company — the layered problem33:09 – What they built on top: Snowflake Intelligence, Tableau, reverse ETL34:15 – Claude Code and context management: shared learning across repos36:04 – The ROI of AI is the ROI of WiFi38:09 – The bifurcation: who becomes unstoppable vs. who plateaus41:03 – One thing to remember: 10,000 prompts is the new 10,000 hours🔗 Connect with Jonathan Hansing: https://www.linkedin.com/in/jonathanhansing🔗 Explore Wallabi: https://www.wallabi.ai🔗 Explore more interviews: https://checkpluris.com/expert-interviewsProof of Work is the podcast of Pluris, a platform connecting investors and operators with the world's leading applied AI experts. Each episode features the builders, operators, and investors who've actually put AI into production, turning it from buzzword to bottom line through sharp case studies and practical conversations. We explore how AI is used to grow revenue, expand margins, improve operations, and create measurable value inside real businesses.Learn more at checkpluris.comExplore more interviews and connect with experts at https://www.checkpluris.com Subscribe to our newsletter at https://proof-of-work-ai.beehiiv.com/