<a target="_blank" href="https://www.buzzsprout.com/twilio/text_messages/520474/open_sms">Send a text</a>Adrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams and helps shape the technology behind one of the world’s most widely used customer service platforms. He joined Zendesk in 2010 and has played a key role in guiding the company’s product and platform strategy as customer experience continues to evolve in the age of AI. Drawing on years of experience building enterprise software used by service teams around the world, Adrian brings a thoughtful perspective on how AI can help organizations deliver better customer service while allowing people to focus on the work humans do best.In this conversation, we discuss:<ul><li>How customer service evolved from a cost center with rigid scripts and binders into a strategic function where technology helps teams deliver better experiences.</li><li>Why customer service leaders shouldn&apos;t fear automation — and why everyone has a &quot;service debt&quot; that AI can finally help pay down.</li><li>The shift from traditional contact centers to AI-enabled service platforms that help companies respond faster while improving both employee and customer experience.</li><li>Lessons Adrian learned scaling Zendesk from a small product team to a global platform serving 100,000 customers and how product-led growth shaped that journey.</li><li>The critical challenge of moving from non-deterministic, creative AI models to deterministic, reliable solutions necessary for enterprise trust and safety</li><li>The future of context engineering and why the next major leap in AI won&apos;t be about superintelligence, but about building systems that capture and act on the knowledge created in every customer interaction.</li></ul>Resources:<ul><li><a href='https://aiandwork.beehiiv.com/subscribe'>Subscribe to the AI &amp; The Future of Work Newsletter</a></li><li><a href='https://www.linkedin.com/in/adrianmcdermott/'>Connect with Adrian on LinkedIn</a></li><li><a href='https://www.newsweek.com/walmart-celebrates-automation-us-job-cuts-reach-multiyear-high-11107369'>AI fun fact article</a></li><li><a href='https://podcasts.apple.com/us/podcast/ai-and-the-future-of-work-with-charlene-li/id1476885647?i=1000476217022'>On How the impact of the pandemic on leaders, culture, and the evolving nature of work</a></li></ul>

<description>&lt;p&gt;&lt;a target="_blank" href="https://www.buzzsprout.com/twilio/text_messages/520474/open_sms"&gt;Send a text&lt;/a&gt;&lt;/p&gt;&lt;p&gt;Adrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams and helps shape the technology behind one of the world’s most widely used customer service platforms. He joined Zendesk in 2010 and has played a key role in guiding the company’s product and platform strategy as customer experience continues to evolve in the age of AI. Drawing on years of experience building enterprise software used by service teams around the world, Adrian brings a thoughtful perspective on how AI can help organizations deliver better customer service while allowing people to focus on the work humans do best.&lt;/p&gt;&lt;p&gt;&lt;b&gt;In this conversation, we discuss:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;How customer service evolved from a cost center with rigid scripts and binders into a strategic function where technology helps teams deliver better experiences.&lt;/li&gt;&lt;li&gt;Why customer service leaders shouldn&amp;apos;t fear automation — and why everyone has a &amp;quot;service debt&amp;quot; that AI can finally help pay down.&lt;/li&gt;&lt;li&gt;The shift from traditional contact centers to AI-enabled service platforms that help companies respond faster while improving both employee and customer experience.&lt;/li&gt;&lt;li&gt;Lessons Adrian learned scaling Zendesk from a small product team to a global platform serving 100,000 customers and how product-led growth shaped that journey.&lt;/li&gt;&lt;li&gt;The critical challenge of moving from non-deterministic, creative AI models to deterministic, reliable solutions necessary for enterprise trust and safety&lt;/li&gt;&lt;li&gt;The future of context engineering and why the next major leap in AI won&amp;apos;t be about superintelligence, but about building systems that capture and act on the knowledge created in every customer interaction.&lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;Resources:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;&lt;a href='https://aiandwork.beehiiv.com/subscribe'&gt;Subscribe to the AI &amp;amp; The Future of Work Newsletter&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.linkedin.com/in/adrianmcdermott/'&gt;Connect with Adrian on LinkedIn&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.newsweek.com/walmart-celebrates-automation-us-job-cuts-reach-multiyear-high-11107369'&gt;AI fun fact article&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://podcasts.apple.com/us/podcast/ai-and-the-future-of-work-with-charlene-li/id1476885647?i=1000476217022'&gt;On How the impact of the pandemic on leaders, culture, and the evolving nature of work&lt;/a&gt;&lt;/li&gt;&lt;/ul&gt;</description>

Send a text Adrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams and helps shape the technology behind one of the world’s most widely used customer service platforms. He joined Zendesk in 2010 and has played a key role in guiding the company’s product and platform strategy as customer experience continues to evolve in the age of AI. Drawing on years of experience building enterprise software used by service teams around...

AI and the Future of Work: Artificial Intelligence in the Workplace, Business, Ethics, HR, and IT for AI Enthusiasts, Leaders and Academics

380: Customer Service's AI Shift: Zendesk CTO Adrian McDermott on Deterministic AI and Context Engineering

<a target="_blank" href="https://www.buzzsprout.com/twilio/text_messages/520474/open_sms">Send a text</a>To celebrate International Women’s Day, this special compilation episode of AI and the Future of Work revisits powerful moments from past conversations with women leaders shaping technology, artificial intelligence, and the future of work.Across industries and roles, these leaders share reflections on career growth, leadership, resilience, and the barriers women still face in technology and executive leadership. Their stories reveal how confidence, mentorship, and opportunity shape who gets to lead in emerging industries like AI.As artificial intelligence reshapes how organizations operate and how work evolves, representation in the people building and guiding these technologies matters more than ever. Expanding access and opportunity is essential to creating a more innovative and inclusive future of work. Featured Guests<ul><li>Charlene Li – Author, Keynote Speaker &amp; Strategic Advisor. Listen to the full conversation here: [<a href='https://www.buzzsprout.com/520474/episodes/3970637'>https://www.buzzsprout.com/520474/episodes/3970637</a>]</li><li>Daphne Jones – CEO at The Board Curators. Listen to the full conversation here: [<a href='https://www.buzzsprout.com/520474/episodes/12105172'>https://www.buzzsprout.com/520474/episodes/12105172</a>]</li><li>Patty Hatter – President &amp; COO at Opsera. Listen to the full conversation here: [<a href='https://www.buzzsprout.com/520474/episodes/5939122'>https://www.buzzsprout.com/520474/episodes/5939122</a>]</li><li>Mona Sabet – SVP at GCG. Listen to the full conversation here: [<a href='https://www.buzzsprout.com/520474/episodes/16747398'>https://www.buzzsprout.com/520474/episodes/16747398</a>]</li><li>Tess Posner – CEO and Founder at AI4ALL. Listen to the full conversation here: [2019: <a href='https://www.buzzsprout.com/520474/episodes/2207636'>https://www.buzzsprout.com/520474/episodes/2207636</a> - 2025: <a href='https://www.buzzsprout.com/520474/episodes/17326118'>https://www.buzzsprout.com/520474/episodes/17326118</a>] </li></ul> What You’ll Learn<ul><li>Why women often wait until they feel fully qualified before pursuing leadership roles</li><li>How imposter syndrome shapes career decisions and confidence in tech</li><li>Why perfectionism can limit growth for technical leaders</li><li>How hiring practices based on brand signals reinforce gender imbalance</li><li>Why diversity in AI development leads to better technology outcomes</li><li>How leaders can expand opportunity for the next generation of women in tech</li></ul>💬 Inspired by something you heard in this episode? Share your favorite insight about leadership, risk-taking, or expanding opportunity for women in AI and tech, and tag us on social.And don’t forget to subscribe to AI and the Future of Work for more conversations with the leaders shaping the future of work.

<description>&lt;p&gt;&lt;a target="_blank" href="https://www.buzzsprout.com/twilio/text_messages/520474/open_sms"&gt;Send a text&lt;/a&gt;&lt;/p&gt;&lt;p&gt;To celebrate International Women’s Day, this special compilation episode of &lt;em&gt;AI and the Future of Work&lt;/em&gt; revisits powerful moments from past conversations with women leaders shaping technology, artificial intelligence, and the future of work.&lt;/p&gt;&lt;p&gt;Across industries and roles, these leaders share reflections on career growth, leadership, resilience, and the barriers women still face in technology and executive leadership. Their stories reveal how confidence, mentorship, and opportunity shape who gets to lead in emerging industries like AI.&lt;/p&gt;&lt;p&gt;As artificial intelligence reshapes how organizations operate and how work evolves, representation in the people building and guiding these technologies matters more than ever. Expanding access and opportunity is essential to creating a more innovative and inclusive future of work.&lt;/p&gt;&lt;p&gt;&lt;b&gt;&lt;br/&gt;Featured Guests&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;Charlene Li – Author, Keynote Speaker &amp;amp; Strategic Advisor. Listen to the full conversation here: [&lt;a href='https://www.buzzsprout.com/520474/episodes/3970637'&gt;https://www.buzzsprout.com/520474/episodes/3970637&lt;/a&gt;]&lt;/li&gt;&lt;li&gt;Daphne Jones – CEO at The Board Curators. Listen to the full conversation here: [&lt;a href='https://www.buzzsprout.com/520474/episodes/12105172'&gt;https://www.buzzsprout.com/520474/episodes/12105172&lt;/a&gt;]&lt;/li&gt;&lt;li&gt;Patty Hatter – President &amp;amp; COO at Opsera. Listen to the full conversation here: [&lt;a href='https://www.buzzsprout.com/520474/episodes/5939122'&gt;https://www.buzzsprout.com/520474/episodes/5939122&lt;/a&gt;]&lt;/li&gt;&lt;li&gt;Mona Sabet – SVP at GCG. Listen to the full conversation here: [&lt;a href='https://www.buzzsprout.com/520474/episodes/16747398'&gt;https://www.buzzsprout.com/520474/episodes/16747398&lt;/a&gt;]&lt;/li&gt;&lt;li&gt;Tess Posner – CEO and Founder at AI4ALL. Listen to the full conversation here: [2019: &lt;a href='https://www.buzzsprout.com/520474/episodes/2207636'&gt;https://www.buzzsprout.com/520474/episodes/2207636&lt;/a&gt; - 2025: &lt;a href='https://www.buzzsprout.com/520474/episodes/17326118'&gt;https://www.buzzsprout.com/520474/episodes/17326118&lt;/a&gt;] &lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;&lt;br/&gt;What You’ll Learn&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;Why women often wait until they feel fully qualified before pursuing leadership roles&lt;/li&gt;&lt;li&gt;How imposter syndrome shapes career decisions and confidence in tech&lt;/li&gt;&lt;li&gt;Why perfectionism can limit growth for technical leaders&lt;/li&gt;&lt;li&gt;How hiring practices based on brand signals reinforce gender imbalance&lt;/li&gt;&lt;li&gt;Why diversity in AI development leads to better technology outcomes&lt;/li&gt;&lt;li&gt;How leaders can expand opportunity for the next generation of women in tech&lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;💬 Inspired by something you heard in this episode?&lt;br/&gt;&lt;/b&gt;Share your favorite insight about leadership, risk-taking, or expanding opportunity for women in AI and tech, and tag us on social.&lt;/p&gt;&lt;p&gt;And don’t forget to subscribe to AI and the Future of Work for more conversations with the leaders shaping the future of work.&lt;/p&gt;</description>

Send a text To celebrate International Women’s Day, this special compilation episode of AI and the Future of Work revisits powerful moments from past conversations with women leaders shaping technology, artificial intelligence, and the future of work. Across industries and roles, these leaders share reflections on career growth, leadership, resilience, and the barriers women still face in technology and executive leadership. Their stories reveal how confidence, mentorship, and opportunity sha...

Confidence, Bias, and Opportunity: Lessons from Women Leaders in Tech Building the Future of AI and Work (International Women’s Day Special Episode)

<a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new">Send us Fan Mail</a>Matt Britton is Founder and CEO of Suzy and a leading voice on how AI and generational change are reshaping business. He is the author of the best-selling book Generation AI: Why Generation Alpha &amp; The Age of AI Will Change Everything, and has advised more than half of the Fortune 500 on marketing, innovation, and consumer behavior. Drawing on decades of experience working with global brands, Matt examines why AI is shifting the economy from knowledge tasks to creative problem solving, why reskilling will define the next decade, and how leaders can build organizations that elevate human judgment in an AI-driven world.In this conversation, we discuss:<ul><li>Why AI is accelerating a shift from memorization and knowledge tasks toward creativity, critical thinking, and real problem solving.</li><li>Why reskilling, not upskilling, will define the next decade and why that transition will be harder than most leaders admit.</li><li>How Gen Alpha, the first AI-native generation, will reshape expectations around work, brands, privacy, and employer relationships.</li><li>Why robotics will transform the service economy sooner than most leaders expect, and what that means for jobs.</li><li>The mistake companies make when they chase AI tools instead of focusing on the most important problems to solve.</li><li>How hyper-personalization and an “audience of one” are redefining trust, value creation, and meritocracy in business.</li></ul>Resources:<ul><li><a href='https://aiandwork.beehiiv.com/subscribe'>Subscribe to the AI &amp; The Future of Work Newsletter</a></li><li><a href='https://www.linkedin.com/in/mattbbritton/'>Connect with Matt on LinkedIn</a></li><li><a href='https://www.storyboard18.com/how-it-works/gen-alpha-expects-ai-led-offices-robot-co-workers-and-30-minute-commutes-iwg-study-84807.htm'>AI fun fact article</a></li><li><a href='https://podcasts.apple.com/us/podcast/kai-nunez-vice-president-of-research-insights-at/id1476885647?i=1000538139208'>On How Kai Nunez, Vice President of Research &amp; Insights at Salesforce, is making tech teams take ownership of AI ethics</a></li></ul>

<description>&lt;p&gt;&lt;a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new"&gt;Send us Fan Mail&lt;/a&gt;&lt;/p&gt;&lt;p&gt;Matt Britton is Founder and CEO of Suzy and a leading voice on how AI and generational change are reshaping business. He is the author of the best-selling book &lt;em&gt;Generation AI: Why Generation Alpha &amp;amp; The Age of AI Will Change Everything&lt;/em&gt;, and has advised more than half of the Fortune 500 on marketing, innovation, and consumer behavior. Drawing on decades of experience working with global brands, Matt examines why AI is shifting the economy from knowledge tasks to creative problem solving, why reskilling will define the next decade, and how leaders can build organizations that elevate human judgment in an AI-driven world.&lt;/p&gt;&lt;p&gt;&lt;b&gt;In this conversation, we discuss:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;Why AI is accelerating a shift from memorization and knowledge tasks toward creativity, critical thinking, and real problem solving.&lt;/li&gt;&lt;li&gt;Why reskilling, not upskilling, will define the next decade and why that transition will be harder than most leaders admit.&lt;/li&gt;&lt;li&gt;How Gen Alpha, the first AI-native generation, will reshape expectations around work, brands, privacy, and employer relationships.&lt;/li&gt;&lt;li&gt;Why robotics will transform the service economy sooner than most leaders expect, and what that means for jobs.&lt;/li&gt;&lt;li&gt;The mistake companies make when they chase AI tools instead of focusing on the most important problems to solve.&lt;/li&gt;&lt;li&gt;How hyper-personalization and an “audience of one” are redefining trust, value creation, and meritocracy in business.&lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;Resources:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;&lt;a href='https://aiandwork.beehiiv.com/subscribe'&gt;Subscribe to the AI &amp;amp; The Future of Work Newsletter&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.linkedin.com/in/mattbbritton/'&gt;Connect with Matt on LinkedIn&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.storyboard18.com/how-it-works/gen-alpha-expects-ai-led-offices-robot-co-workers-and-30-minute-commutes-iwg-study-84807.htm'&gt;AI fun fact article&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://podcasts.apple.com/us/podcast/kai-nunez-vice-president-of-research-insights-at/id1476885647?i=1000538139208'&gt;On How Kai Nunez, Vice President of Research &amp;amp; Insights at Salesforce, is making tech teams take ownership of AI ethics&lt;/a&gt;&lt;/li&gt;&lt;/ul&gt;</description>

Send us Fan Mail Matt Britton is Founder and CEO of Suzy and a leading voice on how AI and generational change are reshaping business. He is the author of the best-selling book Generation AI: Why Generation Alpha &amp; The Age of AI Will Change Everything, and has advised more than half of the Fortune 500 on marketing, innovation, and consumer behavior. Drawing on decades of experience working with global brands, Matt examines why AI is shifting the economy from knowledge tasks to creative pr...

379: AI and the End of the Knowledge Economy: Gen Alpha, Reskilling, and the Rise of Creative Work, with Matt Britton, Founder and CEO of Suzy

<a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new">Send us Fan Mail</a>Kourtney Cross is a RiseUp with ServiceNow Graduate and Business Analyst at Leidos. With a background in accounting and operations, Kourtney saw a shift happening in the enterprise tech landscape and decided he wouldn&apos;t be left behind. He immersed himself in a new ecosystem, earned multiple certifications through the RiseUp program, and built his own hands-on projects to prove his skills to skeptics.But his story isn&apos;t just about learning new software. It&apos;s about the grit it takes to pivot your career in public. Kourtney joins Dan Turchin to share what it really looks like to go from &quot;credentials on paper&quot; to delivering value in the AI economy, and why he believes compounded effort always yields success.In this conversation, they discuss:<ul><li>Why Kourtney saw a market shift and decided to dive in headfirst, and how that decision became a pivotal career inflection point.</li><li>How RiseUp with ServiceNow program enables ambitious early-career professionals to obtain certifications, build real skills, and pivot into future-proof tech roles.</li><li>What certifications actually do, and don’t do, in the job market, and how Kourtney differentiated himself by building and showcasing a hands-on project.</li><li>How to proactively leverage AI as a business analyst, from writing user stories to tightening requirements, instead of fearing job displacement.</li><li>Where AI should accelerate productivity and where clear human boundaries still matter, especially in high-stakes areas like healthcare and admissions decisions.</li><li>Why patience, resilience, and what Kourtney calls “compounded effort” matter more than credentials alone when breaking into tech and building long-term career momentum.</li></ul>Resources:<ul><li><a href='https://aiandwork.beehiiv.com/subscribe'>Subscribe to the AI &amp; The Future of Work Newsletter</a></li><li><a href='https://peoplereign.io/take-the-ai-pledge/?utm_source=podcast&amp;utm_medium=organic&amp;utm_campaign=certification&amp;utm_term=episode378'>AI @ Work – Level One Leaders certification</a></li><li><a href='https://www.linkedin.com/in/kourtney-cross1/'>Connect with Kourtney on LinkedIn</a></li><li><a href='https://www.techtarget.com/searchhrsoftware/tip/How-organizations-can-reskill-and-upskill-employees-in-AI'>AI fun fact article</a></li><li><a href='https://podcasts.apple.com/us/podcast/jonathan-siddharth-ceo-of-turing-on-unleashing-human/id1476885647?i=1000656145498'>On how AI can unleash human potential</a></li><li>Explore more about <a href='https://www.servicenow.com/standard/other-documents/snu-riseup-with-servicenow.html'>RiseUp with ServiceNow</a></li></ul>

<description>&lt;p&gt;&lt;a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new"&gt;Send us Fan Mail&lt;/a&gt;&lt;/p&gt;&lt;p&gt;Kourtney Cross is a RiseUp with ServiceNow Graduate and Business Analyst at Leidos. With a background in accounting and operations, Kourtney saw a shift happening in the enterprise tech landscape and decided he wouldn&amp;apos;t be left behind. He immersed himself in a new ecosystem, earned multiple certifications through the RiseUp program, and built his own hands-on projects to prove his skills to skeptics.&lt;/p&gt;&lt;p&gt;But his story isn&amp;apos;t just about learning new software. It&amp;apos;s about the grit it takes to pivot your career in public. Kourtney joins Dan Turchin to share what it really looks like to go from &amp;quot;credentials on paper&amp;quot; to delivering value in the AI economy, and why he believes compounded effort always yields success.&lt;/p&gt;&lt;p&gt;&lt;b&gt;In this conversation, they discuss:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;Why Kourtney saw a market shift and decided to dive in headfirst, and how that decision became a pivotal career inflection point.&lt;/li&gt;&lt;li&gt;How RiseUp with ServiceNow program enables ambitious early-career professionals to obtain certifications, build real skills, and pivot into future-proof tech roles.&lt;/li&gt;&lt;li&gt;What certifications actually do, and don’t do, in the job market, and how Kourtney differentiated himself by building and showcasing a hands-on project.&lt;/li&gt;&lt;li&gt;How to proactively leverage AI as a business analyst, from writing user stories to tightening requirements, instead of fearing job displacement.&lt;/li&gt;&lt;li&gt;Where AI should accelerate productivity and where clear human boundaries still matter, especially in high-stakes areas like healthcare and admissions decisions.&lt;/li&gt;&lt;li&gt;Why patience, resilience, and what Kourtney calls “compounded effort” matter more than credentials alone when breaking into tech and building long-term career momentum.&lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;Resources:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;&lt;a href='https://aiandwork.beehiiv.com/subscribe'&gt;Subscribe to the AI &amp;amp; The Future of Work Newsletter&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://peoplereign.io/take-the-ai-pledge/?utm_source=podcast&amp;amp;utm_medium=organic&amp;amp;utm_campaign=certification&amp;amp;utm_term=episode378'&gt;AI @ Work – Level One Leaders certification&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.linkedin.com/in/kourtney-cross1/'&gt;Connect with Kourtney on LinkedIn&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.techtarget.com/searchhrsoftware/tip/How-organizations-can-reskill-and-upskill-employees-in-AI'&gt;AI fun fact article&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://podcasts.apple.com/us/podcast/jonathan-siddharth-ceo-of-turing-on-unleashing-human/id1476885647?i=1000656145498'&gt;On how AI can unleash human potential&lt;/a&gt;&lt;/li&gt;&lt;li&gt;Explore more about &lt;a href='https://www.servicenow.com/standard/other-documents/snu-riseup-with-servicenow.html'&gt;RiseUp with ServiceNow&lt;/a&gt;&lt;/li&gt;&lt;/ul&gt;</description>

Send us Fan Mail Kourtney Cross is a RiseUp with ServiceNow Graduate and Business Analyst at Leidos. With a background in accounting and operations, Kourtney saw a shift happening in the enterprise tech landscape and decided he wouldn't be left behind. He immersed himself in a new ecosystem, earned multiple certifications through the RiseUp program, and built his own hands-on projects to prove his skills to skeptics. But his story isn't just about learning new software. It's about the grit it...

378: From Certifications to Careers: How Reskilling Pathways Are Closing the AI Talent Gap

<a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new">Send us Fan Mail</a>Scott Strickland is Chief Commercial Officer at Wyndham Hotels &amp; Resorts and former Chief Information Officer of Wyndham Hotel Group, where he led technology and AI initiatives across one of the world’s largest hospitality portfolios. With experience spanning global operations, enterprise data strategy, and board-level leadership, he has built a reputation for translating business priorities into scalable technology execution.Drawing on that experience, Scott brings a pragmatic lens to how organizations align AI with business strategy, prioritize initiatives by ROI and time to value, and scale responsibly while building trust across teams.In this conversation, we discuss:<ul><li>How Scott translates business needs into technical AI execution while keeping a sharp focus on measurable dollar impact.</li><li>Why winning board support for AI requires the “4 E’s” framework, and how making AI a recurring agenda item changes the trajectory of investment.</li><li>How to scale from four initial AI use cases to more than 340 by prioritizing ROI, time to value, and data readiness.</li><li>Why AI works best as a co-pilot that removes friction and drudgery, rather than as a replacement for frontline teams.</li><li>What it takes to build trust with employees during AI transformation, including transparency, reskilling pathways, and new roles like AI coaches.</li><li>Why security, privacy, and risk management must be built into AI initiatives from day one, and how servant leadership creates the cultural foundation for responsible adoption.</li></ul>Resources:<ul><li><a href='https://aiandwork.beehiiv.com/subscribe'>Subscribe to the AI &amp; The Future of Work Newsletter</a></li><li><a href='https://www.linkedin.com/in/scott-strickland-76b08b2/'>Connect with Scott on LinkedIn</a></li><li><a href='https://www.bbc.com/news/articles/cz913ylq3k3o'>AI fun fact article</a></li><li><a href='https://podcasts.apple.com/us/podcast/wade-foster-zapier-co-founder-and-ceo-discusses/id1476885647?i=1000640235908'>On how the journey from intern to a $5B unicorn happens</a></li></ul>

<description>&lt;p&gt;&lt;a target="_blank" href="https://www.buzzsprout.com/520474/fan_mail/new"&gt;Send us Fan Mail&lt;/a&gt;&lt;/p&gt;&lt;p&gt;Scott Strickland is Chief Commercial Officer at Wyndham Hotels &amp;amp; Resorts and former Chief Information Officer of Wyndham Hotel Group, where he led technology and AI initiatives across one of the world’s largest hospitality portfolios. With experience spanning global operations, enterprise data strategy, and board-level leadership, he has built a reputation for translating business priorities into scalable technology execution.&lt;/p&gt;&lt;p&gt;Drawing on that experience, Scott brings a pragmatic lens to how organizations align AI with business strategy, prioritize initiatives by ROI and time to value, and scale responsibly while building trust across teams.&lt;/p&gt;&lt;p&gt;&lt;b&gt;In this conversation, we discuss:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;How Scott translates business needs into technical AI execution while keeping a sharp focus on measurable dollar impact.&lt;/li&gt;&lt;li&gt;Why winning board support for AI requires the “4 E’s” framework, and how making AI a recurring agenda item changes the trajectory of investment.&lt;/li&gt;&lt;li&gt;How to scale from four initial AI use cases to more than 340 by prioritizing ROI, time to value, and data readiness.&lt;/li&gt;&lt;li&gt;Why AI works best as a co-pilot that removes friction and drudgery, rather than as a replacement for frontline teams.&lt;/li&gt;&lt;li&gt;What it takes to build trust with employees during AI transformation, including transparency, reskilling pathways, and new roles like AI coaches.&lt;/li&gt;&lt;li&gt;Why security, privacy, and risk management must be built into AI initiatives from day one, and how servant leadership creates the cultural foundation for responsible adoption.&lt;/li&gt;&lt;/ul&gt;&lt;p&gt;&lt;b&gt;Resources:&lt;/b&gt;&lt;/p&gt;&lt;ul&gt;&lt;li&gt;&lt;a href='https://aiandwork.beehiiv.com/subscribe'&gt;Subscribe to the AI &amp;amp; The Future of Work Newsletter&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.linkedin.com/in/scott-strickland-76b08b2/'&gt;Connect with Scott on LinkedIn&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://www.bbc.com/news/articles/cz913ylq3k3o'&gt;AI fun fact article&lt;/a&gt;&lt;/li&gt;&lt;li&gt;&lt;a href='https://podcasts.apple.com/us/podcast/wade-foster-zapier-co-founder-and-ceo-discusses/id1476885647?i=1000640235908'&gt;On how the journey from intern to a $5B unicorn happens&lt;/a&gt;&lt;/li&gt;&lt;/ul&gt;</description>

Send us Fan Mail Scott Strickland is Chief Commercial Officer at Wyndham Hotels &amp; Resorts and former Chief Information Officer of Wyndham Hotel Group, where he led technology and AI initiatives across one of the world’s largest hospitality portfolios. With experience spanning global operations, enterprise data strategy, and board-level leadership, he has built a reputation for translating business priorities into scalable technology execution. Drawing on that experience, Scott brings a pr...

377: How Wyndham Hotels Aligns AI with Business Strategy to Empower People at Work, with CCO Scott Strickland

Host Dan Turchin, PeopleReign CEO, explores how AI is changing the workplace. He interviews thought leaders and technologists from industry and academia who share their experiences and insights about artificial intelligence and what it means to be human in the era of AI-driven automation. Learn more about PeopleReign, the system of intelligence for IT and HR employee service: http://www.peoplereign.io.

AI and the Future of Work: Artificial Intelligence in the Workplace, Business, Ethics, HR, and IT for AI Enthusiasts, Leaders and Academics

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