Prompt This
Greg and Clint sit down with John Sasson, a veteran sales leader who’s proving that AI isn’t just a tech trend, it’s a sales performance engine. John shares how his team uses AI to sharpen communication, accelerate research, and turn B-players into A-players. From faster ramp-up to better pipeline quality, he shows how AI is giving reps something they haven’t had in years: freedom.
John also reveals how AI is reshaping management itself. What was once a dreaded performance-review slog is now a meaningful coaching conversation, thanks to AI-driven summaries that combine both the rep’s and the manager’s voices. And beyond his sales team, John highlights how “AI agents” are automating repetitive workflows so both salespeople and customers can move faster.
From quality pipeline to quality of life, this episode is a front-row seat to how AI is quietly revolutionizing the sales profession—from the inside out.
Today's Guest
John Sasson is a Vice President of Sales at a Fortune 100 enterprise software company. With a career spanning startups, government, and global tech firms, John bridges the worlds of policy, process, and performance. He’s a passionate advocate for using AI to augment sales teams—not replace them—unlocking higher engagement, better communication, and faster results.
AI Challenge – Join In!
This week’s AI Challenge is inspired by John’s favorite use case—AI-powered performance reviews.
Your mission: Use ChatGPT or a similar tool to generate a performance review.


Upload an email thread, meeting transcript, or chat exchange.


Add your company’s performance framework or review template.


Ask AI to summarize strengths, growth areas, and next-step recommendations.


You’ll walk away with a surprisingly human, insight-packed review—and maybe your team’s best career conversation yet.
👉 Visit promptthis.ai/blog/how-to-use-chatgpt-to-write-employee-performance-reviews for this week's performance review challenge.
👉 Visit promptthis.ai/ai-challenges for other challenges and to share your results with the community.
Chapter Breakdown
00:00 – Intro & Setup Greg and Clint frame the episode around how AI is transforming real-world sales teams.
02:12 – Meet John Sasson From startups to Fortune 100, John’s view of AI across industries.
04:45 – The AI Sales Advantage How AI turns intuition into impact—and B-players into A-players.
06:20 – Better Pipelines, Smarter Research Why AI-driven prep is giving reps faster insights and higher-quality pipeline.
08:40 – Coaching with AI How John uses AI inside Oracle’s HCM tools to make performance reviews meaningful.
12:45 – Nine AI Agents and Counting What happens when AI dramatically reduces wait times in running government.
15:00 – Freedom to Sell Again How AI is restoring independence and confidence to frontline reps.
18:30 – The Silver Tsunami  Why AI is saving government employees from burnout, not replacing them.
21:40 – Personal AI Assistants John’s dream of a concierge-style AI that knows when the tuna are biting.
25:20 – AI Challenge Recap Transforming performance reviews into a hands-on AI exercise.
 

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