AI-Powered Pitches: How One CEO Used ChatGPT to Build a Winning Proposal

When tasked with delivering a high-stakes RFI and RFP during the holiday season, Dave Gaines, CEO of Media By Mother, turned to generative AI instead of disrupting his team's time off. The pitch was for a global multinational client, typically requiring a team and weeks of effort, but Gaines decided to experiment with ChatGPT. He used it not as a shortcut, but as a research assistant—training it with strategic insights, marketing data, and financial reports to construct a comprehensive proposal in record time.

Gaines built AI-driven “channels” filled with books on strategy, ad tech, dynamic content evolution, and business reports from the client and its competitors. By structuring his inputs, he could extract deep insights—such as key revenue drivers and CEO-level KPIs—far beyond surface-level analysis. The result? A pitch that answered complex market questions across multiple regions without the need for local teams. The client was impressed enough to advance Media By Mother to the next round, despite their lack of global offices.

While the agency didn’t ultimately win, the experiment proved AI’s potential in scaling expertise. Gaines is now integrating these learnings into an internal training program, teaching his team how to use AI as an ally rather than a threat. 

Read more at Digiday.