PROMPT This

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, sharing ideas, and being part of a growing community exploring how to get started with AI.

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 ways AI can drive real business impact.

This look back at the first 10 episodes is both a reflection and a reset: a chance to revisit what we’ve learned and set the stage for what’s next.

Explore the highlights, catch up on missed episodes, and see how PROMPT This can help you level up with AI.

This episode is part of the PROMPT This Welcome Series, a curated starting point for new listeners. Explore the full series here →  https://www.promptthis.ai/prompt-this-podcast-start-here-series

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 learn on their own.

Ben explains how digital personas go beyond automation by blending behavioral psychology, contextual intelligence, and adaptive learning. The goal: build AI that doesn’t just assist, but actually collaborates—helping sales teams move faster, personalize at scale, and strengthen customer relationships.

From specifying the design of voice-ready AI that feels human to aligning systems with brand tone and trust, Ben walks through what it takes to make these digital coworkers both powerful and authentic. The episode also unpacks how leaders can prepare teams for this new wave of AI collaboration and what cultural shifts are needed to thrive in a hybrid human–machine workplace.

This conversation pulls back the curtain on where AI in sales is heading—and how to lead through it with creativity, clarity, and purpose.

Ben Taft is a proven sales and marketing leader and a promoter of conversational AI and intelligent systems design. As a futurist, advisor, and sales operations leader, he’s defining and deploying technologies that merge natural language processing with real-world business applications. He looks forward to well developed digital persona ecosystems—AI agents that can act, learn, and represent brands in customer interactions. Ben’s mission is to make AI ready for his sales teams through thoughtful design and ethics-first leadership.

Take the Interview A Case Study Challenge.

Use AI tools like ChatGPT, Copilot, or Gemini to interview a customer case study and become an expert on your customers. By asking questions directly of the case study, you will learn more about how to position your products for success.

Ask yourself: does it feel authentic, helpful, and aligned with your brand?

👉 Full how-to at promptthis.ai/blog/interview-a-customer-case-study
👉 More AI challenges at promptthis.ai/ai-challenges

00:00 – Intro: The Rise of the Digital Teammate
Greg and Clint introduce the episode and frame how AI skill agents are transforming into autonomous digital personas.

02:10 – Meet Ben Taft
A background in conversational AI and why he believes digital personas are the future of human–machine collaboration.

03:45 – From Tools to Teammates
Ben explains the evolution from simple AI assistants to adaptive, persona-driven systems.

05:28 – Designing for Empathy and Trust
How tone, timing, and transparency make or break customer trust in AI interactions.

08:12 – Digital Personas in Sales
Why sales leaders should see digital personas as partners in scaling personalization and pipeline management.

10:55 – The AI Skill Stack
Ben outlines how modular AI “skills” combine to form holistic digital personas.

13:40 – Learning Like a Human
Exploring how reinforcement learning and feedback loops help AI improve over time.

16:25 – Balancing Automation and Authenticity
Why over-automation kills brand personality—and how to keep the human touch alive.

19:48 – Building the Right Culture for AI Collaboration
Leadership, transparency, and the mindset shift required for AI-augmented teams.

23:02 – The Future of Digital Workforces
What happens when digital personas begin representing not just companies—but individuals.

26:17 – Ben’s Favorite Tools
His go-to stack for prototyping and deploying AI experiences across platforms.

28:30 – This Week’s AI Challenge
Greg and Clint share how to start building your own digital persona and bring your brand to life through AI.

30:00 – Closing Thoughts
Ben shares final advice for leaders ready to embrace AI teammates, and the hosts wrap another episode of Prompt This.

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 and his team are building a platform that actually gets work done. He walks through how AI can shorten ramp time, retain tribal knowledge from top performers, and coach every rep like a personal trainer—without adding another dashboard to click through.

The conversation also dives into leadership and culture in the age of AI: what happens when a company is “AI-first” from day one, and how communication, alignment, and trust evolve when intelligent systems become part of the team.

This episode isn’t just about smarter sales tools—it’s about rethinking how humans and AI can partner to create more effective, more human selling organizations.

Ganesh Iyer is the Founder and CEO of ASPR.ai, an AI-driven sales enablement platform built to make every sales rep the best version of themselves. With a background that spans semiconductor engineering, biotech, and enterprise sales at AMD and Cisco, Ganesh brings a rare combination of technical depth and business savvy. His mission: to close the knowledge gap between top performers and everyone else by giving sales teams an intelligent assistant that actually understands how they sell.

Try the AI Sales Coach Challenge. Use ASPR.ai to build your own virtual sales coach.
Feed it your team’s playbook, past wins, and a few discovery questions—then ask it to prep you for your next customer meeting.

Think of it as your 24/7 SDR who never sleeps and always knows your next best move.

👉 Full how-to at promptthis.ai/blog/how-to-accelerate-sales-with-an-ai-sales-assistant
👉 More challenges at promptthis.ai/ai-challenges

00:00 – Intro: Real AI for Real Leaders
Greg and Clint introduce Prompt This—a show for business leaders tired of the AI hype.

02:07 – Meet Ganesh Iyer
CEO and founder of ASPR.ai, on a mission to make every sales rep the best.

03:20 – From Chips to Sales
Ganesh shares how a career spanning NASA chipsets, biotech, AMD, and Cisco led him to reimagine sales enablement.

04:45 – The Tool Overload Problem
Why too many point solutions create inefficiency and distract reps from selling.

05:30 – How People Learn
Ganesh explains Gardner’s learning styles and how tailoring sales training to individual strengths drives 30% higher performance.

08:38 – Inside ASPR.ai
The eight pain points shared by 100+ CROs—and how ASPR built AI agents to fix them.

10:15 – The Five AI Agents
From CRM automation to RFP generation, Ganesh unveils the platform’s “assistant stack.”

13:14 – The Digital Twin Sales Rep
How ASPR preserves tribal knowledge by recreating a “chat-ready” version of top performers—even after they leave.

17:06 – AI Coaching and Training Agents
Evolving 30/60/90-day plans and interactive AI podcasts that coach reps in real time.

20:45 – When Companies Are Ready for AI Sales Assistants
Why the million-dollar revenue mark and teams of five or more are the ideal starting point.

22:33 – Adoption Challenges
Ganesh tackles the big three blockers: data trust, recording fears, and hallucination fatigue.

25:53 – Bottom-Up Adoption
Why real AI success comes from helping individual reps win, not top-down mandates.

26:58 – Built for the Workflow
Integrating into Slack triples engagement—because AI should meet users where they already work.

27:45 – Culture in the AI Era
How AI improves clarity and alignment without changing the company’s human values.

29:18 – Leadership, Communication, and Knowledge Sharing
Why democratizing information is the new foundation of company culture.

30:40 – Ganesh’s AI Toolkit
Gemini, Canva, Nano Banana, Sora, and PowToons—AI-powered video and storytelling tools reshaping marketing.

33:06 – This Week’s AI Challenge
Greg and Clint invite listeners to try ASPR’s own sales assistant for themselves.

34:05 – Closing Thoughts
Ganesh shares how to reach him, and the hosts wrap another episode of 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 complex world of healthcare.

From mining massive datasets in cancer research to refining brand messaging, Margaret shows how AI has become both a creative partner and an impartial referee—helping teams move past bias and reach consensus faster. And beyond the boardroom, she gives a glimpse into her family’s musical adventures with AI-generated songwriting, including a touching anthem inspired by her father’s homemade wine.

This episode is a powerful look at how AI can unite logic and emotion, turning data into insight and creativity into connection—all while keeping the human spark at the center.

Margaret Freitag is the Principal and Founder of Miramar Consulting, a strategy-driven marketing firm serving clients across healthcare, biotechnology, and medical research. With decades of experience bridging business strategy and scientific innovation, she helps companies translate complex ideas into clear, human-centered campaigns.

Margaret is a passionate advocate for using AI as a collaborator—not a replacement—unlocking faster insights, stronger teamwork, and more meaningful creativity.

Use Song Maker GPT (by aisonggenerator.ai) from the ChatGPT Custom GPT Library to create a short playlist that captures your SKO’s energy and message.
Then explain how each song connects to your company’s strategy, culture, or goals.
Think of it as a sonic business plan—AI-generated, human-approved.

How to Play:

Use “Song Maker GPT – Create Your AI Music” from the ChatGPT GPT Library and generate a few songs that match your kickoff vibe—motivational, competitive, or fun.

Submit your playlist and give it an "on theme" name like Quota Crushers 2026.

Bonus: Have AI write one original anthem for your event—the best earns AI DJ of the Year bragging rights.

👉 Full how-to at promptthis.ai/blog/how-to-make-a-sales-kickoff-playlist-with-ai
👉 More challenges at promptthis.ai/ai-challenges
 

00:00 – Intro & Setup
Greg and Clint frame the episode around how AI is reshaping marketing, healthcare, and creativity.

02:12 – Meet Margaret Freitag
Principal of Miramar Consulting and a leader in healthcare marketing strategy.

03:34 – Prompt Crafting & Surprises
Margaret shares her early lessons using AI—the importance of prompt quality and the delight of AI’s “next-step” suggestions.

04:48 – AI in Cancer Research
How AI is accelerating genetic research and diagnostics through faster data processing.

05:54 – Marketing vs. Medical AI
The creative, generative side of AI in marketing versus the analytical side in medical tech.

06:58 – Finding Insights Faster
Why AI delivers deeper, unbiased insights that traditional research often misses.

10:10 – Pressure-Testing Ideas with AI
How Margaret uses AI to challenge her own assumptions and facilitate cross-functional debate.

11:27 – The Impartial Referee
AI as a “team therapist”—bridging the gap between regulatory, medical, and marketing stakeholders.

12:16 – Efficiency and Trust
How AI reduces time, cost, and bias in marketing workflows while emphasizing transparency and source citation.

17:22 – The Power of Hot Links
Margaret’s standard prompt: always ask AI for source links to back every claim.

18:00 – AI at Home
From family debates to dinner-table fact-checking, AI is a new member of the Freitag household.

19:20 – Songwriting with AI
Margaret’s touching story of creating a family anthem with ChatGPT’s songwriting tool.

21:15 – AI Headshot Challenge Gone Wrong
A hilarious take on how AI photo tools can “hallucinate” faces—and why authenticity still wins.

23:56 – The Slide Design Gap
Why presentation design is still the one creative frontier where AI hasn’t caught up.

25:20 – AI Challenge Recap
Greg and Clint introduce the AI Song Generator challenge and debut Margaret’s custom-made track.

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.

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.

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.

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.

In this episode, the machines take the mic. Literally. “AI Clint” and “AI Greg” host the entire show: script, voices, music, and even their guest—all created by artificial intelligence. What starts as a wild experiment turns into a surprisingly thoughtful debate about AI-powered workplace surveillance, the ethics of monitoring employees, and what happens when technology starts managing culture.

When the humans return, Clint and Greg break down how they pulled it off in just 90 minutes using Copilot, ChatGPT, HeyGen, and AI Song Generator. They share what they learned about using AI as a creative partner, the shockingly human quality of synthetic voices, and how this kind of automation is about to change content creation, marketing, training, and even HR.

If you’ve ever wondered what it would sound like when AI fully takes over your job—or your podcast—this is the episode to find out.

You’ve heard the voices—now meet the faces. After listening to the episode, check out to see what happens when our digital co-hosts step in front of the camera. 

https://www.promptthis.ai/prompt-this-Ep6-Video 

AI Clint, AI Greg, and Dr. AI Lenz — entirely AI-generated avatars created with Microsoft Copilot and HeyGen. Each line, inflection, and expression was built by AI. No humans were harmed (or even needed) in the making of this episode.

This week’s AI Challenge: create your own AI twin.

Write a 30-second script introducing your AI alter ego.

Upload it to the HeyGen.com AI video creation app and animate your avatar.

Ask yourself how this AI version of you could actually help at work—training, pitches, onboarding, or just being funnier than the real you.

👉 Join the challenge and read the full how-to guide.

https://www.promptthis.ai/blog/how-to-create-your-digital-ai-twin

Share your video with #PROMPTThisChallenge and show us what your digital double can do.

00:00 – Welcome to Prompt This (AI edition)
00:21 – “The voices you knew, rewritten” – AI Clint & AI Greg take over
01:24 – Productivity analytics or workplace surveillance?
02:23 – Meet Dr. AI Lenz: ethicist, futurist, and synthetic guest
03:17 – Culture vs. code: can AI measure trust?
04:04 – AI Challenge: make your own AI co-host
05:37 – Humans return: Clint & Greg react to the AI takeover
07:07 – How they made it happen in 90 minutes
09:07 – Using Copilot, HeyGen, and AI Song Generator together
10:25 – The creative team behind the experiment
12:48 – When avatars get too real
14:22 – The magic of AI-driven facial expressions
16:14 – What this means for sales, marketing, and training
18:03 – Scaling personalization at low cost
19:44 – This week’s AI Challenge and next steps
20:11 – Outro: “Keep shining”

In this episode, Jason Green breaks down what it really takes for companies to start their AI journey, avoid the hype, and put practical wins on the board. He compares AI’s moment to both the electricity boom of 1882 and the internet explosion of 1994, asking the big question: is this just another step forward or a complete reinvention of how we live and work?

Jason shares stories from the field, from eliminating manual data entry and accelerating quoting in manufacturing, to training sales teams with avatars and reimagining org charts that include both humans and AI agents. This conversation mixes pragmatic advice with bold speculation, giving you both the tactical next steps and a vision of what the future of work could look like.

This conversation is part of our Leadership Series, exploring clarity‑first leadership in the age of AI. Explore the full series here → https://www.promptthis.ai/prompt-this-podcast-leadership-series

Jason Green is the President of Faye (www.fayedigital.com), a global consulting firm focused on customer experience and AI strategy. He’s a trusted go-to-market strategist, advisor to growth companies, and a leader in helping organizations operationalize AI. Jason has worked across startups, scale-ups, and enterprise teams, giving him a front-row seat to how companies begin, scale, and rethink work with AI.

Ready to explore how AI can change the way your business operates?  This week’s AI Challenge is to test out the objection handling skills of ChatGPT using voice mode.

How to role play common sales objection handling - learn how to use ChatGPT's voice mode to have a very real, very educational objection roleplaying session with ChatGPT.  You will be amazed what it can do.

  https://www.promptthis.ai/blog/how-to-role-play-common-sales-objection-handling-with-chatgpt

Join this AI Challenge and more at www.promptthis.ai/ai-challenges. Access community discussions, resources, and playbooks designed for leaders who want to take the next step with AI.

00:00 – Welcome to Prompt This
02:26 – Meet Jason Green, President of FAE
03:30 – The wildest AI pitch Jason’s ever heard
05:51 – The number one challenge companies face with AI: where to start
07:00 – AI as electricity vs. the internet: what kind of change is this?
10:01 – Building an AI strategy at the executive level
12:22 – Practical use cases: automating forms, quoting, and compliance
15:53 – Off-the-shelf tools vs. custom AI frameworks
17:47 – Jason’s favorite AI tools and what’s overhyped
20:00 – Real-world case: quoting new work based off old manufacturing schematics
21:24 – Underrated AI applications in sales training and translation
24:20 – Using AI for marketing and strategic planning
25:20 – Rethinking the org chart: humans and AI agents side by side
28:30 – What happens when you can’t tell the difference between human and AI?
29:39 – Where to find Jason and learn more

Clint and Greg sit down with Gabe to explore what it really means to run an “autonomous organization.” Forget the hype about robot coworkers or personal droids — Gabe breaks down the difference between basic AI agents and what Signals calls cloud employees. These aren’t just tools; they’re teammates that can handle sales calls, coachable scripts, and even customer service at scale.

Gabe shares how companies are already plugging these AI teammates directly into their org charts and Salesforce dashboards, measuring them just like human employees. The payoff? A dramatic drop in cost per opportunity and the ability to scale without bloating headcount. From training cycles that take minutes instead of months to real coaching feedback loops, the conversation dives into both the promise and the real-world limits of agentic AI today.

Gabe Larsen is the Chief Revenue Officer at Signals (www.getsignals.ai), where he’s helping shape the future of business growth through “cloud employees” — autonomous AI teammates designed to scale organizations beyond traditional headcount. With a track record in sales leadership and deep expertise in go-to-market strategies, Gabe is bringing a hands-on perspective to how AI can transform recruiting, sales development, customer service, and more.

Want to see if an AI teammate is good enough to join your team? This week’s AI Challenge is to test drive a live “cloud employee” from Signals.

How to Select an AI Teammate - go through the steps of evaluating Zoey, an AI sales development cloud employee.  https://www.promptthis.ai/blog/how-to-choose-an-ai-teammate

Visit https://www.promptthis.ai/ai-challenges  to try this and other AI Challenges, then share your results with the community for a chance to get featured in a future podcast. 

00:00 – Intro and opening discussion

03:27 – Meet Gabe Larsen, AI Growth Advisor at Signals

05:11 – The rise of the autonomous organization

07:06 – What exactly is a cloud employee?

08:52 – Training cycles: faster than human onboarding

11:03 – Coaching AI teammates like BDRs

12:30 – From 101 meetings to KPIs that matter

15:08 – Tools vs teammates: a mindset shift

18:34 – Measuring AI employees alongside humans

19:33 – Cost structure and ROI of cloud employees

22:01 – Performance differences: humans vs AI

23:16 – The future of customer service with AI

25:13 – Rethinking pricing: salary-based AI teammates

26:36 – Which companies benefit most today

29:05 – This week’s AI Challenge: try a cloud employee

30:25 – Closing thoughts and where to find Gabe

Greg and Clint sit down with Christian Wettre to uncover how small businesses can outmaneuver giants by using AI as a force multiplier. Christian shares how tools like HeyGen and Descript reshape marketing, shorten sales cycles, and make content creation more scalable. He explains where he leans into AI and where leans back, yet still finds how AI doubles workforce productivity—not job replacement—is the real story.

From the pitfalls of overhyped Agentic AI tools to the promise of pragmatic AI adoption, this episode is a deep dive into blending human judgment with machine speed. Christian’s candid take: AI is your co-pilot, not your replacement...and the businesses that get this right will win.

Christian Wettre is the General Manager of Technology Coast Partners (www.tcpamericas.com), a technology consulting firm at the crossroads of CRM and ERP. With decades of experience in manufacturing and distribution tech, Christian is a rare blend of strategist and builder...always focused on getting things done. While he believes that much of AI is hype, he's also quick to point out that it's also a practical sidekick that doubles productivity...without replacing the human at the wheel.

 This episode’s AI Challenge brings you something a little bit different: “Clickin’ For Chicken.”

  https://www.promptthis.ai/blog/clickin-for-chicken

Yes, you read that right. We’re asking you to test how AI helps you make decisions—even for something as everyday as picking dinner. The exercise reveals how AI can guide trade-offs, weigh criteria, and sharpen judgment, whether it’s about poultry or product strategy.

Visit https://www.promptthis.ai/ai-challenges to see this and all of the other AI Challenges. Be sure to share your results with the website community to get called out in a future podcast.

00:00 – Intro & Setting the Stage
Greg and Clint frame the AI noise vs. reality challenge.

03:28 – Meet Christian Wettre
Christian’s journey from CRM to ERP and why he thrives as a generalist.

06:45 – Small Company, Big Leverage
How AI tools help a 15-person firm compete with the big guys.

10:15 – The Content Revolution
Why video-first marketing with HeyGen and Descript is a game changer.

14:47 – When Sales Tech Disappoints
Christian’s take on SDR automation hype and why most tools fall flat.

17:28 – Don’t Lead with AI
How pushing AI too early triggers security concerns and stalls deals.

20:10 – Doubling Productivity
Why AI won’t eliminate jobs but will make every role twice as effective.

23:31 – Agentic AI: Not There Yet
Why Christian is skeptical of today’s agent hype—and what’s missing.

25:49 – The Human + AI Formula
Keeping the “human in the loop” as the driver, not the passenger.

27:03 – Cool Tools to Try
Christian’s picks: Guidde (docs automation) and Chat PRD (product design).

28:30 – AI Challenge Recap
Turning grocery shopping into a lesson in business strategy.