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Promptly Speaking

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by Sara Roberts

5.0(3 reviews)
18 episodes
Updated Daily
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Podcast Overview

Promptly Speaking is your guide to navigating the AI revolution without losing your mind—or your job. We bridge the gap between complex technology and real-world application for professionals, creatives, and business leaders. If you are asking questions like: 🤔 "Will AI replace my job?" 🤔 "Is AI making us dumber?" 🤔 "How do I lead a team through this disruption?" ...then this channel is for you. We move beyond the "Tool of the Week" to provide deep dives into AI Strategy, Cognitive Offloading, AI Ethics, and the Future of Work. Whether you are a corporate executive, a solopreneur, or a parent concerned about screen time, we provide the frameworks you need to stay relevant and resilient. New episodes every Tuesday.

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Publishing Since

10/9/2025

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Recent Episodes

Episode thumbnail for Building a People-First Approach for AI with Jason Stover

July 7, 2026

Building a People-First Approach for AI with Jason Stover

<p><strong>What if AI could make your employees feel more valued, not less?</strong></p><p>Jason Stover, Executive Vice President at SSA Group and the builder behind Scout — SSA's internal AI platform — joins Sara and Dan to share how a people-first philosophy is driving one of the most thoughtful AI adoption strategies in the hospitality industry. From getting laid off teams through COVID, to discovering ChatGPT and not sleeping for weeks, to accidentally sending an AI-written email that almost got him flipped off by a colleague, Jason's story is equal parts honest, funny, and genuinely inspiring.</p><p>Key takeaways:</p><ul><li>Why the hospitality industry may be more AI-resistant than most — and why that's a strategic advantage</li><li>How Scout was born, and what makes it different from generic AI tools</li><li>The fight-flight-freeze response to AI adoption, and how to move your team past it</li><li>Why AI adoption strategy starts with one question: "How does this impact me?"</li><li>The email incident that changed how Jason thinks about AI communication forever</li><li>How SSA is using behavioral psychology to personalize the AI experience for each employee</li><li>What it really means to lead with empathy when rolling out new technology</li><li>Why giving a long-tenured employee a four-day week might be the best ROI AI can deliver</li><li>Jason's honest take on the future of work and the industries most at risk</li><li>The number one piece of advice for any business leader who is still dancing around the AI topic</li></ul><br/><p>Connect with Jason Stover: <a href="https://www.linkedin.com/in/jason-stover-4b6b7a1b/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/jason-stover-4b6b7a1b/</a></p><p>Follow Sara &amp; Dan: Sara: <a href="https://www.linkedin.com/in/saralynneroberts/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/saralynneroberts/</a> </p><p>Dan: <a href="https://www.linkedin.com/in/danroberts27/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/danroberts27/</a> </p><p>Email the show: <a href="mailto:hello@promptlyspeakingpod.com" rel="noopener noreferrer" target="_blank">hello@promptlyspeakingpod.com</a></p><p>00:00 Episode preview &amp; intro</p><p>01:15 Jason's parallel path: people &amp; tech</p><p>01:43 Digital scales &amp; predictive analytics</p><p>03:11 How Jason stays curious about AI</p><p>03:51 The YouTube channels he follows</p><p>04:44 EVP blocking Fridays for AI discovery</p><p>04:54 Journey from dishwasher to VP at SSA</p><p>06:38 The pivot: stepping down to focus on AI</p><p>06:47 COVID, layoffs, and the ChatGPT moment</p><p>09:47 Why it's always about people, not just AI</p><p>10:21 Meet Scout — SSA's internal AI platform</p><p>10:56 Tank Stover: the persona that started it all</p><p>14:08 Early feedback: fight, flight, or freeze</p><p>15:33 How employees are actually using Scout</p><p>17:26 Building career paths with AI in hospitality</p><p>18:10 Building trust in AI tools with frontline staff</p><p>18:47 The million-dollar question: transparency</p><p>19:55 What most CIOs get wrong about rollout</p><p>20:46 Trips and falls along the way</p><p>20:57 The email incident that changed everything</p><p>24:17 Rethinking who to bring AI to first</p><p>26:05 Repurposing saved hours for human connection</p><p>27:14 AI helping us be more human</p><p>27:41 Tangible vs. soft ROI of AI investment</p><p>28:47 The four-day workweek conversation</p><p>31:59 How Scout connects siloed departments</p><p>33:21 Crystal ball: the future of SSA with AI</p><p>36:15 Demographics, retention &amp; daily pay</p><p>39:10 Leading with empathy — advice for leaders</p><p>39:31 Stop freezing: come up with a strategy</p><p>40:39 What Jason admires about Anthropic &amp; Claude</p><p>41:13 A united leadership team behind the vision</p><p>42:16 Advice for young people navigating AI</p><p>43:04 Behavioral Essentials &amp; personalizing Scout</p><p>46:20 The data trust problem</p><p>46:40 Using AI to discover your own strengths</p><p>47:18 Where to find SSA &amp; closing thoughts</p><p>47:41 Outro</p>

Episode thumbnail for Vibe Coding Your Way to Job Security in the Age of AI

June 23, 2026

Vibe Coding Your Way to Job Security in the Age of AI

<p><strong>What if you could build your company's next internal tool in a weekend, for $30?</strong></p><p>Aaron Trockman is a partner manager at Glean who had zero formal coding experience — and then built PartnerSync, a fully functional partner automation platform used daily across his sales organization, in about 10 hours using AI tools. In this episode, Sara and Dan sit down with Aaron to unpack exactly how he did it, what tools he used, what it actually cost, and what it means for the future of work. Aaron's story is a clear signal: AI is democratizing product development, and professionals who embrace these tools will have a massive advantage.</p><p><strong>Key Takeaways:</strong></p><ul><li>Aaron built a working MVP for around $30 in AI credits using Base44, then migrated to Lovable + Supabase.</li><li>His AI workflow: dump the problem into Glean → generate a prompt with Prompt Cowboy → build in Lovable → debug with Gemini/ChatGPT.</li><li>The tool he built, PartnerSync, replaced a capability they were evaluating from Crossbeam at significant additional cost.</li><li>Key principle: assess complexity and margin for error before committing — internal tools with ~5–10% error tolerance are ideal for vibe coding.</li><li>AI is democratizing product development — a team of one can now ship what once required a team of five.</li><li>The future of work isn't AI replacing jobs — it's people who use AI replacing people who don't.</li><li>The platform play is shifting: companies are building custom internal tooling instead of buying bloated SaaS they only use 30–40% of.</li><li>Prompting tips: assign AI a persona (researcher, UX engineer), tell it to forget its last approach, and switch tools when you hit a wall.</li><li>Job security comes from making your team more effective — not just from being able to build.</li><li>Aaron's one action for listeners: take your biggest problem right now and ask ChatGPT, Gemini, or Glean how to solve it. Just start.</li></ul><br/><p>Connect with Aaron Trockman: <a href="https://www.linkedin.com/in/aarontrockman/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/aarontrockman/</a></p><p>Sara: <a href="https://www.linkedin.com/in/saralynneroberts/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/saralynneroberts/</a> </p><p>Dan: <a href="https://www.linkedin.com/in/danroberts27/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/danroberts27/</a> </p><p>Email the show: <a href="mailto:hello@promptlyspeakingpod.com" rel="noopener noreferrer" target="_blank">hello@promptlyspeakingpod.com</a></p><p>00:00 Intro &amp; cold open</p><p>00:47 What is Glean? Sara's pitch</p><p>02:06 Aaron's role: partner manager</p><p>02:54 Building PartnerSync — the story</p><p>04:57 Replacing a $$$$ SaaS tool for $30</p><p>06:06 The AI workflow: start to finish</p><p>07:11 Prompt Cowboy &amp; prompt engineering</p><p>07:52 Base44 vs Lovable — why he switched</p><p>08:57 What is throttling? Plain language</p><p>09:46 Total cost: under $100 to MVP</p><p>10:33 Sara's Lovable build attempt</p><p>12:13 When AI lies about APIs</p><p>12:50 AI = brilliant dev with ADHD</p><p>14:55 How to scope AI-built projects</p><p>16:25 ISVs, internal use &amp; margin for error</p><p>16:54 How to push through roadblocks</p><p>17:57 Prompting as building a team of one</p><p>18:53 Three hours on a multi-model build</p><p>20:40 Job security in the AI era</p><p>21:46 AI democratizes product development</p><p>24:47 How AI changed Aaron's mindset</p><p>25:41 Someone using AI will take your job</p><p>26:24 What Aaron wants to build next</p><p>27:39 Scope: too big vs. your wheelhouse</p><p>29:56 The future of SaaS &amp; the platform play</p><p>31:21 One action to take in 30 minutes</p><p>32:16 Outro</p>

Episode thumbnail for Podcast Update & House Tour

January 13, 2026

Podcast Update & House Tour

<p>We're taking a short break to upgrade our equipment &amp; set! </p><p>In this episode, Sara gives a brief tour of their home &amp; recording spaces, highlighting the challenges they've faced and the changes they plan to make. </p><p>Subscribe so that you don't miss new episodes! Be back soon!!</p>

18 total episodes available

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Frequently asked questions

Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.

What is Promptly Speaking?

Promptly Speaking is your guide to navigating the AI revolution without losing your mind—or your job. We bridge the gap between complex technology and real-world application for professionals, creatives, and business leaders.

If you are asking questions like: 🤔 "Will AI replace my job?" 🤔 "Is AI making us dumber?" 🤔 "How do I lead a team through this disruption?" ...then this channel is for you.

We move beyond the "Tool of the Week" to provide deep dives into AI Strategy, Cognitive Offloading, AI Ethics, and the Future of Work. Whether you are a corporate executive, a solopreneur, or a parent concerned about screen time, we provide the frameworks you need to stay relevant and resilient.

New episodes every Tuesday.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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