Today we’re talking to David DeWolf, Founder & CEO of Knownwell. We discuss the impacts and takeaways of David’s silent retreat, the perils that business leaders are facing with AI, and how he’s helping to solve these problems with a human-centered vision.

All of this right here, right now, on the Modern CTO Podcast! 

To learn more about Knownwell, check out their website here.

Have feedback about the show? Let us know here.

Produced by ProSeries Media.

For booking inquiries, email [email protected]

About David DeWolf

David DeWolf is the founder and CEO of Knownwell, an AI solutions company that is reinventing the way businesses are understood and run in the Intelligence Economy.

Previously he was the Founder and CEO of 3Pillar Global, a digital product development organization that he grew to become the preeminent provider within one of the hottest sectors within technology services. Under David’s leadership, 3Pillar grew for 16 consecutive years to more than 2000 employees. 3Pillar operated in 10 countries and was named to the Inc. 5000, a list of the fastest-growing private companies in the US, ten separate times. David is the co-author of The Product Mindset and has been featured in Fortune, Forbes, Fast Company, and Inc. among others.

David is the Managing Member of DeWolf Family Ventures, a Family Office that invests in and supports the next generation of principled entrepreneurs and leaders. Over his career, as an operator, David has raised over $500mm of capital. He has delivered a 4.55x MOIC to investors and driven a 43% IRR across 5 separate funding rounds (3.80x MOIC and 96% IRR on a weighted average basis).

David is a frequent keynote speaker at events. David is passionate about leadership, entrepreneurship, and digital innovation. He serves on the Boards of various for profit and non-profit organizations including Chairman of Capango, where he is currently the Lead Investor, and a Private Equity Backed Marketing-as-a-Service business, where he serves as Independent Board Member. We served as the Vice Chairman of the Board at the Franciscan University of Steubenville for 8 years and is currently finishing up his 12 year term as a Trustee. Prior to founding 3Pillar, David held multiple technology leadership positions, was an active member of the Apache Software Foundation.

About Knownwell

Knownwell, an AIaaS platform company, synthesizes an organization’s natural communications, enterprise data, and public information into actionable intelligence to minimize client churn, maximize client growth, and drive operational efficiency. Knownwell equips mid-market professional services executives with the competitive edge they need—knowing their clients to strengthen client relationships, manage service quality perception, and calibrate alignment. To explore more about Knownwell’s transformative platform, please visit

Joel Beasley

Joel Beasley founded the Modern CTO Podcast in 2017 while writing his book, the Modern CTO book, with the goal of interviewing CTOs and sharing their experiences with others in the tech community.

Joel’s conversational style and insightful questions quickly gained traction, attracting high-profile guests such as Microsoft’s CTO, Kevin Scott, and T-Mobile’s CIO, Cody Stanford. With each episode, the podcast’s popularity continued to grow, and soon, Joel found himself with a waiting list of future guests.

Today, the Modern CTO Podcast has become the number one leadership and tech podcast in the world, with over 150k active listeners, including CTOs, lead developers, and rising tech leaders. Joel’s commitment to creating a conversational atmosphere for his guests to share their experiences has inspired a new generation of leaders and innovators.

As the success of the podcast grew, Joel founded ProSeries Media, a podcast production company that helps companies worldwide create their own podcasts. With a team of producers, content creators, and podcast bookers, ProSeries Media produces over ten shows, providing a platform for companies to connect with their audience and share their expertise.

Through his work on the Modern CTO Podcast and ProSeries Media, Joel Beasley has become a respected voice in the tech industry, inspiring others to share their knowledge and insights with the wider community. His passion for creating engaging content that informs, inspires, and entertains has made him a sought-after speaker and advisor on all things tech.

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