Promptly Speaking

Building a People-First Approach for AI with Jason Stover


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What if AI could make your employees feel more valued, not less?

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.

Key takeaways:

  • Why the hospitality industry may be more AI-resistant than most — and why that's a strategic advantage
  • How Scout was born, and what makes it different from generic AI tools
  • The fight-flight-freeze response to AI adoption, and how to move your team past it
  • Why AI adoption strategy starts with one question: "How does this impact me?"
  • The email incident that changed how Jason thinks about AI communication forever
  • How SSA is using behavioral psychology to personalize the AI experience for each employee
  • What it really means to lead with empathy when rolling out new technology
  • Why giving a long-tenured employee a four-day week might be the best ROI AI can deliver
  • Jason's honest take on the future of work and the industries most at risk
  • The number one piece of advice for any business leader who is still dancing around the AI topic

Connect with Jason Stover: https://www.linkedin.com/in/jason-stover-4b6b7a1b/

Follow Sara & Dan: Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: [email protected]

00:00 Episode preview & intro

01:15 Jason's parallel path: people & tech

01:43 Digital scales & predictive analytics

03:11 How Jason stays curious about AI

03:51 The YouTube channels he follows

04:44 EVP blocking Fridays for AI discovery

04:54 Journey from dishwasher to VP at SSA

06:38 The pivot: stepping down to focus on AI

06:47 COVID, layoffs, and the ChatGPT moment

09:47 Why it's always about people, not just AI

10:21 Meet Scout — SSA's internal AI platform

10:56 Tank Stover: the persona that started it all

14:08 Early feedback: fight, flight, or freeze

15:33 How employees are actually using Scout

17:26 Building career paths with AI in hospitality

18:10 Building trust in AI tools with frontline staff

18:47 The million-dollar question: transparency

19:55 What most CIOs get wrong about rollout

20:46 Trips and falls along the way

20:57 The email incident that changed everything

24:17 Rethinking who to bring AI to first

26:05 Repurposing saved hours for human connection

27:14 AI helping us be more human

27:41 Tangible vs. soft ROI of AI investment

28:47 The four-day workweek conversation

31:59 How Scout connects siloed departments

33:21 Crystal ball: the future of SSA with AI

36:15 Demographics, retention & daily pay

39:10 Leading with empathy — advice for leaders

39:31 Stop freezing: come up with a strategy

40:39 What Jason admires about Anthropic & Claude

41:13 A united leadership team behind the vision

42:16 Advice for young people navigating AI

43:04 Behavioral Essentials & personalizing Scout

46:20 The data trust problem

46:40 Using AI to discover your own strengths

47:18 Where to find SSA & closing thoughts

47:41 Outro

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Promptly SpeakingBy Sara Roberts