DataFramed

Technology is now moving faster than the organizations trying to adopt it. A model can be tested in an afternoon, but the approval to test it can take half a year, and that gap is where most transformation budgets quietly disappear. The structures that made companies safe and predictable — layers of sign-off, centralized control, standardized processes — were built for a world where getting things wrong was expensive. That world is gone. So what actually has to change inside a company for AI to deliver value? Which habits are holding things up? And where do you start when everything needs fixing at once?
Phil Le Brun is an Executive in Residence at AWS and previously spent over 25 years at McDonald's Corporation, where he was VP of Global Technology Development and International CIO. Jana Werner is an Executive in Residence at AWS, where she leads the Financial Services Practice in EMEA and advises Fortune 500 executive teams on transformation, having previously scaled a tech start-up to acquisition by HP, led digital transformation at Tesco Bank, and advised DHL on global change. Together they are the authors of The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation (Harvard Business Review Press).
In the episode, Richie, Phil and Jana explore why AI transformations stall, the Tin Man organization and its anti-patterns, the octopus as a model for adaptive companies, why AI adoption metrics mislead, being data informed rather than data driven, making fast reversible decisions, hiring and onboarding, embedding learning into daily work, and much more.
Links Mentioned in the Show:
• The Octopus Organization (book)
• Through the Looking-Glass — Lewis Carroll (the Red Queen)
• Goodhart's law
• Annie Duke on "resulting"
• Linda Hill, Harvard Business School
• A Seat at the Table — Mark Schwartz
• Connect with Phil
• Connect with Jana
• AI-Native Course: Intro to AI for Work
• Related Episode: Your 90 Day Blueprint for AI Success with Charlene Li
• Explore AI-Native Learning on DataCamp
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Four years into the AI boom, headlines still promise agents that will run entire departments, yet most companies can't point to the transformation they were sold. The gap isn't intelligence — today's models are remarkably capable — it's context: no model arrives knowing how your company actually gets things done. For anyone tasked with deploying AI at work, this raises pressing questions. What does it take to turn generic intelligence into something that understands your specific operations? And why do so many well-funded AI initiatives stall before they ever reach production?
Jennifer Smith is Co-Founder and CEO of Scribe, the Workflow AI platform used by more than 6 million people and 94% of the Fortune 500. Under her leadership, Scribe has surpassed $100M in ARR and raised $75M at a $1.3B valuation. Before founding Scribe, Jennifer spent three years at Greylock Partners interviewing 1,200 C-suite executives about the problems they were trying to solve, and previously worked at Coatue Management and McKinsey & Company. She holds an MBA from Harvard and a BA from Princeton.
In the episode, Richie and Jennifer explore why AI agents haven't taken over knowledge work yet, harnessing institutional knowledge as "specialized intelligence," mapping enterprise workflows with LLMs, building the business case and ROI for AI transformation, balancing top-down and bottom-up change management, and the agency-driven skills that matter most in an AI-native workplace, and much more.
Links Mentioned in the Show:
Scribe (Jennifer's company)
McKinsey & Company
Aaron Levie, CEO of Box, followed by Jennifer on X
Jaya Gupta, Partner at Foundation Capital
Connect with Jennifer: LinkedIn
AI-Native Course: Intro to AI for Work
Related Episode: AI Agents at Work: What Actually Breaks (and How to Fix It) with Danielle Crop, EVP at WNS

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Software buying decisions used to be made once, by someone far removed from the people actually using the tool. That model is breaking down. Teams now expect software to work out of the box, without weeks of setup, integration, and configuration before anyone sees value. At the same time, a growing share of "users" aren't people at all — they're AI agents calling the same systems through APIs and chat interfaces. That raises a set of questions worth sitting with: what happens to user experience when the user isn't human? Can personalization and simplicity coexist, or is one always traded for the other? And as building software gets cheaper, what actually separates a good product from a cluttered one?
Srini Raghavan is Chief Product Officer at Freshworks, where he leads product strategy for the company's AI-powered customer and employee experience software. He previously served as Chief Product Officer at RingCentral and SVP of Product at Five9, and holds an MBA from the University of Chicago Booth School of Business.
In the episode, Richie and Srini explore the SaaS consolidation trend and why the "SaaSpocalypse" prediction missed the point, building software that works for both humans and AI agents, how MCP and modular architecture are reshaping product design, the rise of the "product builder" role replacing specialized titles, customer feedback loops and cohort-based A/B testing, judgment as the most important AI-era career skill, and much more.
Links Mentioned in the Show:
• Fresh Service — https://www.freshworks.com/freshservice/
• Jaya Gupta's Webinar at RADAR - https://app.datacamp.com/learn/webinars/whats-next-rethinking-analytics-for-the-ai-human-era
• Freddy AI Agent Studio — https://www.freshworks.com/freshservice/ai-agent-studio/
• Figma Make — https://www.figma.com/make/
• Cursor — https://cursor.com
• NotebookLM — https://notebooklm.google/
• Marc Andreessen's "Mexican standoff" comment — https://officechai.com/ai/programmer-product-manager-and-designer-roles-are-merging-into-a-single-builder-role-marc-andreessen/
• Connect with Srini: https://www.linkedin.com/in/srinivasan28/
• AI Tutor Course: Intro to AI for Work — https://www.datacamp.com/courses/introduction-to-ai-for-work
• Related Episode: Vibe Coding and the Rise of the Non-Developer Builder with Matt Palmer, Developer Relations at Replit
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Software teams are shipping faster than ever, but speed hasn't solved the oldest problem in the industry: most software still isn't very good. AI coding tools have lowered the barrier to building something, yet they haven't lowered the barrier to building something worth using. As more people who aren't trained software creators start shipping products, a new question is forming across product, design, and engineering teams: if AI can build almost anything, how do you make sure it builds the right thing, and builds it well?
Todd Olson is co-founder and CEO of Pendo, the product experience platform he started in 2013. Before that, he held product and engineering roles at Rally Software, Red Hat, Cisco, and Google. He's the author of The Product-Led Organization and has led Pendo through raising over $356M in venture funding while growing to 2,300+ customers.
In the episode, Richie and Todd explore why bad software still gets built, how much context AI coding agents need before they can be trusted, using behavioral data and "rage prompts" to catch what's actually frustrating users, the shift toward headless and agentic software design, how product, design, and engineering roles are splitting apart, managing one-way-door risk during AI transformation, and much more.
Links Mentioned in the Show:
Jeff Bezos’s one-way door / two-way door decision framework: 2015 Amazon shareholder letter
HubSpot’s 2024 terms-of-service backlash
Ramp
Stripe
Fin (Intercom’s AI agent), recently announced to be acquired by Salesforce
Anthropic / Claude Code
Connect with Todd
AI-Native Course: Intro to AI for Work
Related Episode: The Data Team’s Agentic Future with Ketan Karkhanis, CEO at ThoughtSpot

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As AI takes over more technical and routine work, the skills that set data and AI professionals apart are shifting. Raw technical ability and a high IQ still matter, but they are becoming table stakes as tools get more capable and teams get smarter. What increasingly separates people is harder to automate: communication, self-awareness, authenticity, and the ability to keep learning through failure. For anyone building a career in this space, that raises real questions. Which skills are actually worth investing in now? What holds up as AI advances? And how do you keep growing once you have already had some success?
Dr. Todd Dewett is one of the world's most-watched leadership voices — an authenticity expert, bestselling author, and top LinkedIn Learning instructor whose courses have reached more than 25 million people across 100+ countries. After beginning his career at Andersen Consulting and Ernst & Young, he earned a PhD in organizational behavior at Texas A&M and spent a decade as an award-winning professor before going solo. He is a five-time TEDx speaker and the author of Show Your Ink.
In the episode, Richie and Todd explore why fear quietly limits careers, treating failure as data rather than a verdict, the people skills that outlast raw IQ, learnable self-awareness, authenticity at work, using AI without losing your voice, getting better at speaking and writing, building habits, escaping the success trap, and much more.
Links Mentioned in the Show:
• Todd's LinkedIn newsletter (writing + his "Creswall" comic) — https://www.linkedin.com/in/drdewett/
• Todd Dewett on LinkedIn Learning — https://www.linkedin.com/learning/instructors/todd-dewett
• Free LinkedIn Learning access via your public library — https://www.linkedin.com/learning
• Gemma Leigh Roberts, chartered psychologist — https://www.linkedin.com/in/gemmaleighroberts/
• Erin Shrimpton, chartered organisational psychologist — https://ie.linkedin.com/in/erinshrimpton
• Connect with Todd: https://www.linkedin.com/in/drdewett/
• AI-Native Course: Intro to AI for Work
• Related Episode: How to Have a Machine Learning Career in 2026 with Marina Wyss
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