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PODCAST

PROMPT This

PROMPT This is where thoughtful strategy meets fresh perspectives, guided by cohosts Clint and Greg. Listen in as they explore how AI is reshaping business, leadership, and the decisions that drive both.

technology management

All Episodes

13:37

“Season 1: Ctrl+Alt+Season Finale” featuring Clint...

PROMPT This ·

2026/04/16

Episode SummarySeason 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. What they found is that it already has. Quietly, unevenly, and in ways most people are still missing. In

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36:24

"The CRO’s Field Guide to Real-World AI" featuring...

PROMPT This ·

2026/04/08

Guest IntroductionJason 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, separating what delivers real impact from what just looks good in a demo. Episode Summary This

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20:18

"Clash of the Cohosts: Prompt This Smackdown II"

PROMPT This ·

2026/04/01

Guest IntroductionsTime 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 Hendricks, and Martin Schneider. Clint and Greg draft from this pool and go head to head. No long

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37:09

“AI Can Translate Everything. It Still Can’t Make You...

PROMPT This ·

2026/03/25

GuestJoshua 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 will transform translation, he is clear that it will not eliminate the need for humans. Instead,

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37:07

"From Enterprise Funnels to One‑Click Sales: One...

PROMPT This ·

2026/03/18

Guest IntroductionErikArcher 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. Today he is exploring a different path. Archer is building his passion project. It is a

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25:51

"The Analyst’s View of AI: Judgment, Costs, and...

PROMPT This ·

2026/03/11

Episode SummaryAI 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 analysts. Instead, he discovered something more interesting. Analysts who learn to use AI gain a

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33:15

"Agentic AI Outcomes: Are You Measuring What...

PROMPT This ·

2026/03/04

Guest IntroductionMartin 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 without getting lost in hype. If you run sales, marketing, or customer success, this conversation is about

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25:27

“Command Line Clint Strikes Back…and Claude Gets Put...

PROMPT This ·

2026/02/25

Guest IntroductionIn 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, they pressure test AI in the real world for operators in sales, marketing, and leadership. Today,

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30:02

“A Live Look at How AI Fits into Real Work…and Greg...

PROMPT This ·

2026/02/18

Episode SummaryInstead 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 copied into Lovable. Within minutes, a complete website appears. Navigation works. Pages are

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37:16

"What AI Still Misses in Leadership Coaching"...

PROMPT This ·

2026/02/11

Episode SummaryIn 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 executive coaching, emphasizing that true coaching is not advice-giving or performance management. It is

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28:48

"How to Turn Unstructured Data Into Your Competitive...

PROMPT This ·

2026/02/04

Episode SummaryIn 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, and product decisions are often based on memory, inference, and mood instead of facts. Warren

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42:27

"The Strategy Handoff: Where Good Plans Go Off Track"...

PROMPT This ·

2026/01/28

Episode SummaryStrategy 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 actually running the business. The conversation reframes AI as a management discipline, not a

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36:29

PROMPT This ·

2026/01/21

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 dramatically more capable once they began ingesting high-quality book content, often without

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35:32

"Why AI Literacy Is the Real Power Move for Today's...

PROMPT This ·

2026/01/14

Episode SummaryThis episode of PROMPTThis 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, and why experience, expertise, authority, and trust still matter more than output volume. The

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32:20

"The AI Sandwich: A Workflow Model That Actually...

PROMPT This ·

2026/01/07

Episode SummaryAI 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 fail, not because of tools, but because leaders skip the hard work of vision, goal-setting, and

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34:45

"2025 Year in Review - AI Didn’t Take Our Jobs … Just...

PROMPT This ·

2025/12/31

Episode SummaryThis episode is a straight talk, no-spin review of AI in 2025. These past twelve monthswere the year AI got real, not world-ending, not world-saving, just deeply practical. In thisPROMPTThis 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 AI. From agentic AI and AGI predictions to synthetic media, job fears, and the 90-day learning curve that

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4:49

"PROMPT This Presents: The Holiday Hotline" featuring...

PROMPT This ·

2025/12/24

Episode SummaryIn 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 of dirty data. An inventory bot stuck in 1997 highlights what happens when models are never

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20:09

"PROMPT This Rapid Fire Smackdown"

PROMPT This ·

2025/12/17

Episode SummaryThis episodechanges upthe 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 part truth serum for the AI industry. The conversation cuts through hype and surfaces how experienced

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35:01

"Creativity vs. Productivity: Why Marketers Still...

PROMPT This ·

2025/12/10

Guest IntroductionDeepak 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 teams stand out when AI systems become the first stop for product research. Episode Summary In

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33:24

"Straight Talk on AI: Building Smarter Teams and...

PROMPT This ·

2025/12/03

Episode SummaryIn this episode, Clint and Greg sit down with Chris Angus to explore how 8x8, a leadingcloud-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 analytics, while emphasizing that successful AI adoption starts small—with trusted data. He also pulls back

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33 results

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