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'A GenAI Case Study: Waldo' with Dan Monahan

Episode 7 of the Scale with Strive Podcast podcast, hosted by Scale with Strive, titled "'A GenAI Case Study: Waldo' with Dan Monahan" was published on May 7, 2025 and runs 25 minutes.

May 7, 2025 ·25m · Scale with Strive Podcast

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Welcome to the Scale with Strive podcast, the place where you come to listen to some of the world’s most influential leaders of the SaaS industry. 🚀 Our host is John Hitchen and on today’s episode, we are excited to welcome Dan Monahan, Head of Sales at Waldo! Dan has a rich background in Sales and Leadership within the SaaS Space, beginning his career at ZeroTurnaround (which was later acquired by Perforce), before joining Forestry.io, leading a large Sales and Sales Engineering ...

Welcome to the Scale with Strive podcast, the place where you come to listen to some of the world’s most influential leaders of the SaaS industry. 🚀 

Our host is John Hitchen and on today’s episode, we are excited to welcome Dan Monahan, Head of Sales at Waldo! 

Dan has a rich background in Sales and Leadership within the SaaS Space, beginning his career at ZeroTurnaround (which was later acquired by Perforce), before joining Forestry.io, leading a large Sales and Sales Engineering team. 

Moving on to Snyk, he helped grow the revenue from $30M ARR to $300M ARR - and now he is at the very early stages of Waldo, an AI company focused on research and strategy. 

Today, we focus in on the Gen AI space and the company Dan has recently joined, Waldo. We explore the factors he considered before making his move, what the product does and delve into the competitive space of Gen AI.  

Some of our key takeaways from the conversation were: 

💡 The factors to consider when considering joining an early-stage company 

💡 Exploring Waldo’s AI research platform and its GTM Strategy 

💡 Why sticking to your ICP, even in a busy market, is key  

 

Let’s Dive in! 

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Connect with Dan here - https://www.linkedin.com/in/danieljohnmonahan/

Connect with John here - https://www.linkedin.com/in/johnhitchen/

Learn more about Strive here - https://scalewithstrive.com/

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0:00            Introduction to Dan 

3:16              Why Dan Joined Waldo

7:33              Waldo's AI Research Platform Explained

11:20            Go-to-Market Strategy and Future Vision

21:09           Building Teams for AI Startups

24:35          Closing Thoughts 


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