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The AI Hackathon Playbook

Release Date: 03/31/2025

AI Knowhow

Want to unlock AI's potential in your organization? Skip the brainstorms and go all in with an AI Hackathon! In this final installment of the Applied AI series, CMO Courtney Baker is joined by CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao to break down why AI hackathons might be your best tool for driving adoption, sparking collaboration, and building lasting impact. Whether you’re a tech startup or a professional services firm, this episode gives you the blueprint. Special guest Jeff Gallimore, Chief Technology and Innovation Officer of Excella, shares best...

Applied AI: Reframing How We Think About AI

AI Knowhow

Still think of AI as just a chatbot? It’s time to reframe that mindset. Logan Kilpatrick of Google DeepMind joins the show to discuss the latest advances with Gemini, including long-context reasoning and native multimodal capabilities—and why UX, not chat, is the real frontier in AI. He shares examples from Khan Academy and others that show how smarter, more human-centered experiences are key to unlocking AI’s full potential. Logan and Mohan Rao also explore why it's such an exciting time to be working in AI, with developers making groundbreaking discoveries daily, and how the next...

Applied AI: Proactive Leadership with AI

AI Knowhow

The best leaders don’t wait for problems to arise - they anticipate them before they happen. But how do you shift from a reactive leadership style to a proactive one? AI might just be the key. In this episode, host Courtney Baker is joined by Knownwell CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao. Together, they explore how AI enables leaders to foresee challenges, manage risks, and reclaim time for strategic decision-making. From AI-driven notifications that predict client or employee concerns to tools that help leaders focus on what truly matters, they uncover how...

Would You Rather...? (AI Edition)

AI Knowhow

Would you rather trust an AI decision-making system that's 90% accurate but a total black box, or one that's only 70% accurate but fully explainable? What about AI that predicts your next big revenue stream with 30% certainty versus AI that boosts your operations by 70%? In this special 75th episode of AI Knowhow, we put our panel to the test in an AI-themed game of Would You Rather? Knownwell CMO Courtney Baker is joined by CEO David DeWolf and Chief Product and Technology Officer Mohan Rao for a lively debate on AI trade-offs in business. From decision-making transparency to revenue growth...

Applied AI: Using AI to Go From Insights to Execution

AI Knowhow

Your data is trying to tell you something. Are you listening? AI isn’t just about insights. It’s about execution. In this episode of AI Knowhow from Knownwell, CMO Courtney Baker is joined by CEO David DeWolf Chief Product and Technology Officer Mohan Rao to explore how AI is reshaping execution in professional service firms. They discuss how AI can move beyond simple automation to orchestrate strategic execution, aligning teams, prioritizing tasks, and ensuring the right work gets done at the right time. Our special guest, , Co-founder and CTO of April, sits down with Pete to...

AI Hot Takes (2025 Edition)

AI Knowhow

We’re turning up the heat once again! After last year’s sizzling Hot Takes episode, we had to run it back for 2025. Knownwell CMO Courtney Baker is joined by CEO David DeWolf and Chief Product & Technology Officer Mohan Rao to deliver their boldest AI predictions yet. What shifts are coming in AI? Which trends are about to fizzle out? And what might shake up the industry in unexpected ways? In our expert interview segment, Pete Buer sits down with AI and digital transformation expert Dr. Henna Karna, a Harvard Fellow and former Google executive. She shares practical strategies for...

Applied AI: Turning Data Into Actionable Insights

AI Knowhow

Data is pouring into your business every second, but where are the insights you need to act on it? Just 27% of business executives in a recent Forrester study said their data and analytics projects produce actionable insights. In this episode, we look at how AI can help bridge the gap between the overwhelming amounts of data available today and the actionable intelligence executives need to drive results. Knownwell CMO Courtney Baker, CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao kick things off by breaking down the journey from raw data to wisdom. They...

Applied AI: Developing Your AI Roadmap

AI Knowhow

What does an AI roadmap really look like? And how does a corporate AI roadmap differ from a personal one? In this episode of AI Knowhow from Knownwell, host Courtney Baker is joined by Knownwell’s CEO David DeWolf, Chief Product & Technology Officer Mohan Rao, and NordLight CEO Pete Buer to break it all down. First, the team explores how business leaders can chart a clear AI strategy—starting with vision, linking it to business goals, and balancing customer feedback with long-term objectives. David and Mohan share insights on making micro-pivots, avoiding roadmap confusion, and the key...

Scaling AI: Building the Right AI Team

AI Knowhow

You’re smart. You know your business cold. But do you know how to build the right AI team? It’s harder than it looks, and the old innovation playbook just won’t cut it. Pete Buer sits down with Ben Hafele, CEO of and host of The Lean AI Podcast, to discuss how to assemble the right AI team. They explore what skill sets are essential, how to balance technical and strategic talent, and why AI teams need a different structure than traditional innovation groups. As always, host Courtney Baker is joined by CEO David DeWolf and Chief Product & Technology Officer Mohan Rao for a panel...

Scaling AI: How AI Can Break Down Silos in Your Organization

AI Knowhow

Is your organization held back by departmental silos where the necessary data and information doesn't always flow between them? AI might just be the key to breaking these silos down. Pete Buer kicks things off with an interview featuring Josh Okun, Chief Innovation Officer at Gravity Global. Josh shares how AI is helping global teams collaborate across time zones, optimize creative processes, and foster dynamic relationships within organizations. Discover how his team at Gravity Global leverages AI tools like custom GPTs and RAG to turn static brand guidelines into dynamic resources that...

More Episodes

Want to unlock AI's potential in your organization? Skip the brainstorms and go all in with an AI Hackathon!

In this final installment of the Applied AI series, CMO Courtney Baker is joined by CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao to break down why AI hackathons might be your best tool for driving adoption, sparking collaboration, and building lasting impact. Whether you’re a tech startup or a professional services firm, this episode gives you the blueprint.

Special guest Jeff Gallimore, Chief Technology and Innovation Officer of Excella, shares best practices from their GenAI-focused hackathons—including how engaging clients as judges and building cross-functional teams helped move ideas from prototype to production. From enabling constraints to cultural buy-in, Jeff explains how hackathons can be more than just a creative break—they can be a launchpad for real outcomes.

Courtney, David, and Mohan reflect on their own hackathon experiences and offer strategic advice on making hackathons successful—from aligning with your roadmap to ensuring outputs are built to scale. Plus, how non-engineers can thrive in AI innovation thanks to tools like Canva and prompt engineering.

All that PLUS Pete Buer breaks down the rise and fall (and jailbreak) of the Humane AI Pin. The big lesson? Innovation only sticks if it meets the market where it is.

Whether you’re running your first hackathon or looking to level up your next one, this episode is packed with practical tips, real stories, and a bit of good-natured competition.

Want to see what Knownwell’s platform can do with your data? Visit www.knownwell.com to get started.

Watch this episode on YouTube: https://youtu.be/Gu2jq1Ol_Z0

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