PROMPT This

Episode Summary Season One has come to an end and the Prompt This team is taking a well-deserved break after 32 episodes in 32 weeks, dozens of operators, and hours of conversations about AI.  In this season finale, Clint and Greg step back and ask a simple question. What actually changed? The answer is not what you expect. They started this podcast thinking AI might reshape work someday. Wha...

Guest Introduction Jason Rushforth is a seasoned Chief Revenue Officer and career sales operator who has built and scaled high-performing go-to-market teams across multiple organizations. He brings a sharp, field-tested perspective on how deals actually get done, where sales processes break, and how to fix them. More recently, Jason has been hands-on with AI in sales and marketing workflows, separ...

Guest Introductions Time for something a little different and have some fun. This episode brings back the ten most recent Prompt This guests and turns them into "Rapid Fire Smackdown" competitors. You get a mix of CEOs, operators, analysts, and AI builders including Erik Archer Smith, Emily Maxie, Julie Trelstad, Ken Roden, Warren Kucker, Brooks Bush, Bruce Daley, Joshus Gould, Dr. Shelli Hendrick...

Guest Joshua Gould is the Group CEO of thebigword , one of the world’s largest language services and multilingual technology companies. His organization supports governments, healthcare systems, and global enterprises where accuracy is critical and mistakes carry real consequences. He has spent decades at the intersection of language, technology, and global business. While he has long believed AI...

Guest Introduction Erik Archer Smith is a veteran marketing leader with nearly two decades of experience scaling enterprise SaaS companies from early traction to more than $150 million in annual recurring revenue. Over his career he has led demand generation, account-based marketing, brand, and growth teams at companies including CommerceIQ, Treasure Data, Arena, and Scale Venture Partners. &...

Episode Summary AI is changing how knowledge work gets done, but it is not replacing experts the way many people fear. In this episode, Clint and Greg talk with longtime software analyst Bruce Daley about what really happens when experienced professionals start using AI tools in their daily work. Bruce began experimenting with large language models because he believed AI might eventually replace a...

Guest Introduction  Martin Schneider is Vice President and Principal Analyst at Constellation Research. He has sat on both sides of the table as a go-to-market operator and now as an industry analyst advising companies on AI, CRM, and customer experience. In this episode, he joins Clint and Greg to break down what agentic AI is actually delivering in the real world and how to measure it witho...

Guest Introduction In this episode, there is no outside guest. It is just Clint and Greg, and that is the point. Clint is a longtime startup operator who has lived through multiple waves of tech change and knows what it takes to turn big ideas into real execution. Greg built and scaled sales organizations in Silicon Valley and knows how revenue actually gets created inside a company. Together, the...

Episode Summary Instead of interviewing a guest, Clint and Greg run a live demo. The goal is straightforward: can a marketer build a professional website without waiting on developers? The answer is yes. Clint starts by generating a detailed Lovable prompt inside ChatGPT. The LLM researches Greg’s background, identifies positioning themes, and structures a multi-page personal site. That prompt is...

Episode Summary In this episode, the conversation moves away from sales and marketing tactics and into the human core of leadership. Clint and Greg sit down with Shelli Hendricks to explore what executive coaching really is, what it is not, and how AI is starting to intersect with leadership development.  Shelli explains the difference between everyday coaching skills and professional executi...

Episode Summary In this episode, we talk with Warren Kucker about a simple but overlooked idea: companies are sitting on massive amounts of value inside their conversations and doing almost nothing with it. Warren breaks down why AI is not a feature or a product category, but a new way of computing that finally lets us work with human language at scale. We dig into why sales coaching, forecasting,...

Episode Summary Strategy failure rarely starts with bad ideas. It starts with bad translation. In this episode, Clint and Greg sit down with Brooks Busch to unpack why strategy planning and execution remain one of the most consistent failure points inside growing companies. From thousand-slide decks to disconnected OKRs, Brooks explains how most organizations confuse documenting strategy with actu...

Episode Summary This episode explores a topic most business leaders are not thinking about yet, but probably should be. AI systems are built on content, and a huge portion of that content comes from books. In this conversation, we dig into what that means for authors, publishers, and everyday users of AI tools like ChatGPT, Claude, and Gemini. Julie explains how large language models became dramat...

Episode Summary This episode of PROMPT  This is a practical master class on how AI is actually being used inside modern go-to-market teams. Emily Maxie breaks down what it means to be a Chief Growth Officer today, where sales and marketing are no longer separate functions and AI is not a side experiment. She explains why most AI content strategies fail, how “AI slop” has flooded the market, a...

Episode Summary AI adoption is not slow. Leadership clarity is. In this episode, Ken Roden challenges the popular narrative that employees are resisting AI. Based on his research and real-world conversations, the reality is very different. Most employees are already using AI. The real bottleneck is trust in leadership and confidence in how AI fits into the work. Ken explains why many AI pilots fai...

Episode Summary This episode is a straight talk, no-spin review of AI in 2025. These past twelve months were the year AI got real, not world-ending, not world-saving, just deeply practical. In this PROMPT This year-end recap, Greg and Clint look back at the hype cycles, the misses, the breakthroughs, and the many weekends they sacrificed building a podcast powered almost entirely by...

  Episode Summary In this Christmas special, Prompt This takes a playful but pointed look at real-world AI problems through a holiday lens. With Clint and Greg “out of office,” AI Clint and AI Greg man the Elf Tech support hotline, fielding panicked calls from the North Pole. What sounds like seasonal comedy quickly turns into serious business lessons. Double-booked reindeer expose the risks...

Episode Summary This episode changes up the usual format. Instead of long interviews, Clint and Greg host the first ever Prompt This Rapid Fire Smackdown. The rules are simple. Every guest previously answered the same five AI-related questions. Clint and Greg draft teams, go head to head, and let ChatGPT decide which answer wins each round. What follows is part debate, part comedy, and p...

Guest Introduction Deepak Deolalikar is the co-founder of Ziply AI, where he leads strategy for a platform built to help marketing teams create content at scale and stay visible within AI search. He combines deep technical curiosity with a historian’s view of innovation, drawing clear parallels between today’s AI wave and the early commercial internet. His work focuses on helping B2B marketing tea...

Episode Summary In this episode, Clint and Greg sit down with Chris Angus to explore how 8x8, a leading  cloud-based communications provider,  is integrating AI into every layer of its business—from customer conversations to employee training and product innovation. Chris explains how AI is changing the economics of communication through consumption-based pricing and smarter conversation...

Episode Summary This week, Clint and Greg are taking time off for the US Thanksgiving holiday to recharge and reconnect with family and friends. But they didn’t want to leave listeners empty-handed. In the spirit of gratitude, they’re sharing something special—a fully AI-generated song of appreciation created just for the PROMPT This audience. It’s their way of saying thank you for tuning in, shar...

PROMPT This celebrates a milestone with our first 10 episodes completed! In this special recap, Clint and Greg take a look back at the journey so far, highlighting the most impactful lessons and practical insights. Across these episodes, the focus has been on helping business professionals learn how AI can support their work by offering practical insights, building confidence, and showing clear wa...

Episode Summary In this episode of PROMPT This , Greg and Clint dive deep with Ben Taft , a sales operations leader and strategist defining the requirements for the next generation of intelligent sales systems. The conversation explores how “skill agents” are evolving into full-fledged digital personas —AI-driven teammates that can engage customers, manage workflows, and l...

Episode Summary In this episode of Prompt This , Greg and Clint sit down with Ganesh Iyer , the founder of ASPR.ai , to explore how AI sales assistants are quietly reshaping the future of revenue teams. Forget the endless parade of CRM updates—Ganesh’s world is all about intelligent agents that learn, coach, and work alongside human sellers. From pre-meeting prep to post-call CRM updates, Ganesh a...

PROMPT This Greg and Clint sit down with Margaret Freitag , a marketing strategist and founder of Miramar Consulting, who’s proving that AI isn’t just transforming tech—it’s redefining collaboration, creativity, and communication. Margaret shares how her agency uses AI to accelerate research, streamline strategy sessions, and bridge gaps across medical, regulatory, and marketing teams in the compl...