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

Send a text
Scott Strickland is Chief Commercial Officer at Wyndham Hotels & 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:
How Scott translates business needs into technical AI execution while keeping a sharp focus on measurable dollar impact.
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.
How to scale from four initial AI use cases to more than 340 by prioritizing ROI, time to value, and data readiness.
Why AI works best as a co-pilot that removes friction and drudgery, rather than as a replacement for frontline teams.
What it takes to build trust with employees during AI transformation, including transparency, reskilling pathways, and new roles like AI coaches.
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.
Resources:
Subscribe to the AI & The Future of Work Newsletter
Connect with Scott on LinkedIn
AI fun fact article
On how the journey from intern to a $5B unicorn happens

Send a text
In this special February compilation episode of AI and the Future of Work, we explore what it truly takes to build AI companies designed to last.
While AI innovation moves fast, enduring companies are built on fundamentals. Clear problem selection. Thoughtful product design. Ethical intent. Leadership under uncertainty. And the resilience required to keep going when the market pushes back.
This episode brings together insights from founders and operators who have built, scaled, and sustained AI-driven companies across different stages and industries. Their stories reveal a shared truth. Long-term success depends less on hype and more on discipline, courage, and trust.

Featured Guests
Eric Olson, CEO and Co-founder of Consensus - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/11574063 
Rich White, Founder of UserVoice and CEO of Fathom - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/11911533 
Dmitry Shapiro, CEO of MindStudio - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/14866979 
Daniel Marcous, Founder and CTO of April, former CTO of Waze - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/12679210 
George Sivulka, CEO of Hebbia - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/16572788 

What You’ll Learn
Why founders must act before certainty appears
How solving real pain leads to stronger, longer-lasting companies
What ethical intent looks like in practical AI system design
Why trust, accuracy, and discipline matter more than speed
How resilience shapes leadership through uncertainty
What separates durable AI companies from short-lived experiments
Inspired by something you heard in this episode?
Share your favorite insight on social and tag us. We’d love to hear what resonated with you. And don’t forget to subscribe to AI and the Future of Work for more conversations with the founders and leaders shaping what comes next.

Other special episodes: 
Lessons from Four Unicorn CEOs Disrupting Massive Markets with AI (Special Episode)
Artificial General Intelligence: Can Machines Really Think Like Us? (Special Episode)
Ethical AI in Hiring: How to Stay Compliant While Building a Fairer Future of Work (HR Day Special Episode)
AI and the Law: How AI Will Change Legal Careers (Special Episode)
AI and Safety: How Responsible Tech Leaders Build Trustworthy Systems (National Safety Month Special)
Lessons from Leaders: How AI Is Redefining Work and the Human Experience (Labor Day Special Episode)
365: What We’ve Learned from 364 Expert Conversations (Special Episode)

Send a text
Andrea Iorio is one of Brazil’s most requested keynote speakers on digital transformation, innovation, and leadership. His work has reached more than 50,000 people through live talks, and his podcasts have surpassed 300,000 downloads. A former Head of Tinder across Latin America and Chief Digital Officer at L’Oréal Brazil, he brings firsthand experience leading digital change inside large organizations. Today, he advises leaders, teaches MBAs, and studies how AI reshapes work, skills, and decision making. His latest book, Between You and AI, explores how humans stay relevant as machines take on more cognitive tasks.
In this conversation, we discuss:
Why AI replaces tasks rather than entire jobs, and how reframing work around tasks changes how leaders redesign roles, workflows, and value creation.
Andrea shares surprising data from a global HR survey that reveals why 93% of HR leaders prioritize soft skills over hard skills in new hires, and why this trend signals a massive shift in the future of work.
Andrea outlines nine new skills, grouped into Three Pillars of Transformation essential for professionals and leaders: cognitive, behavioral, and emotional.
Why asking better questions matters more than producing answers, and how prompting extends beyond AI inputs into everyday leadership and decision making.
Andrea shares how L’Oréal’s reverse mentoring program shifted the C-Suite’s perspective on emerging digital trends, demonstrating why understanding the Gen Z consumer requires direct immersion over passive presentations.
What the rise of autonomous AI agents means for responsibility, goal setting, and collaboration, and why agency remains a human obligation even as systems gain autonomy.
Resources:
Subscribe to the AI & The Future of Work Newsletter
Connect with Andrea on LinkedIn
AI fun fact article
On how investors decide what to fund in gen AI and what most entrepreneurs get wrong

Send a text
Lynne Chou O’Keefe is the Founder and Managing Partner of Define Ventures, one of the largest early-stage health tech investment firms, with $800 million in assets under management.
With deep experience across digital health, venture capital, and frontline healthcare systems, Lynne brings a clear-eyed view of why the industry is changing now and where AI can make a meaningful difference. 
She is widely recognized for her work backing companies that rethink access, outcomes, and patient experience, and is a trusted voice on how technology, ethics, and human judgment must come together to move healthcare forward.
In this conversation, we discuss:
Why healthcare still runs on fragmented systems and what that means for where AI can truly move the needle.
How the shift from fee-for-service to value-based care changes incentives and pushes the system toward prevention over volume.
Why patients now expect healthcare to work like transportation or food delivery, and how that expectation reshapes care delivery.
The three phases of AI in healthcare, from administrative efficiency to clinical workflow support and, eventually, clinical decision-making.
Where the ethical boundary sits today between AI-assisted care and AI-led decisions, especially when access to care is limited.
Why the future of healthcare is hybrid by design, with AI augmenting clinicians rather than replacing human judgment.
Resources:
Subscribe to the AI & The Future of Work Newsletter
Connect with Lynn on LinkedIn
AI fun fact article
On how AI is fixing the biggest problem faced by doctors.

Send a text
Dave Kellogg is a leading voice in enterprise software, SaaS metrics and go-to-market strategy. A four-time guest on AI and the Future of Work, Dave brings decades of hands-on experience inside SaaS companies to challenge how leaders think about growth, metrics, and execution. He is an Executive-in-Residence at Balderton Capital and the author of Kellblog. His perspective is shaped by years spent leading and advising software businesses from early stages through scale.

In this conversation, we discuss:
Why Dave argues that we are increasingly working for the algorithm, not the other way around, and how that shift shows up in SEO, productivity, and workplace behavior.
Why SaaS is not dying but is under real pressure, and how claims that companies can easily replace systems like Salesforce or Workday misunderstand how enterprise software actually works.
How AI changes jobs by pushing work up the value chain rather than simply eliminating roles, and why history suggests societies adapt faster than we expect.
Why trust becomes more valuable as AI floods the world with low-quality content, and how brands, creators, and leaders must earn credibility in an era of front-run information.
What the move from the Rule of 40 to the Rule of 60 signals about today’s market, and why many mid-scale SaaS companies now face uncomfortable strategic choices.
How venture capital is becoming more financialized, what that means for founders, and why AI may accelerate the shift toward larger funds, bigger bets, and fewer safety nets.
Episode Chapters
00:00 Why Dave Kellogg’s Annual SaaS Predictions Matter More Every Year
03:53 Working for the Algorithm, Not the Other Way Around
06:10 “Death of SaaS”: Why Enterprise Software Isn’t Going Away
08:56 Why Enterprise Software Is Built to Last
11:51 AI and Jobs: Why Work Disappears Differently Than We Expect
16:31 The New Jobs AI Creates and Why Humans Stay Essential at Work
19:22 Why Trust Becomes the Most Valuable Currency in an AI-Driven World
24:23 Why AI Forces Us to Rethink Trust, Media, and Credibility
27:57 Why the Rule of 60 Is Replacing the Rule of 40 for Startups in 2026
33:44 How Venture Capital Is Becoming a Financial Services Business
41:47 Why Silicon Valley’s New Willingness to Take Political Positions Surprised Many Founders
45:57 What the Grateful Dead Can Teach Us About Business, Creativity, and Legacy

Resources:
Subscribe to the AI & The Future of Work Newsletter
Connect with Dave Kellogg on LinkedIn
Kellblog Predictions for 2026
AI fun fact article
On How AI is Making Networks Smart
Previous episodes in AI & The Future of Work featuring Dave:[2025] 324: 2025 predictions with Dave Kellogg: The Future of AI, SaaS, and Business
[2024] Dave Kellogg, SaaS whisperer and EIR at Balderton Capital, predicts the future of AI, Silicon Valley, and venture capital
[2023] Special episode: Dave Kellogg, serial CEO, investor, and SaaS pioneer, shares his (provocative) tech predictions for 2023