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 takes to pivot your career in public. Kourtney joins Dan Turchin to share what it really looks like to go from “credentials on paper” to delivering value in the AI economy, and why he believes compounded effort always yields success.

In this conversation, they discuss:

• Why Kourtney saw a market shift and decided to dive in headfirst, and how that decision became a pivotal career inflection point.
• How RiseUp with ServiceNow program enables ambitious early-career professionals to obtain certifications, build real skills, and pivot into future-proof tech roles.
• 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.
• How to proactively leverage AI as a business analyst, from writing user stories to tightening requirements, instead of fearing job displacement.
• Where AI should accelerate productivity and where clear human boundaries still matter, especially in high-stakes areas like healthcare and admissions decisions.
• Why patience, resilience, and what Kourtney calls “compounded effort” matter more than credentials alone when breaking into tech and building long-term career momentum.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• AI @ Work – Level One Leaders certification
• Connect with Kourtney on LinkedIn
• AI fun fact article
• On how AI can unleash human potential
• Explore more about RiseUp with ServiceNow

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

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

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.

Lynn Thoman is a professor at Columbia University’s School of International and Public Affairs and the founder of 3 Takeaways, a top 1% global podcast known for distilling big ideas from influential leaders shaping policy, business, and society.

Drawing on experience across corporate strategy, public sector advisory work, and board service at institutions such as the Brookings Institution and Harvard’s Kennedy School of Government, Lynn brings a cross-sector lens to how AI is reshaping decision-making, learning, and human potential.

In this conversation, we discuss:

• Why AI is best understood as an amplifier of human capability, especially in leadership, where judgment and choices matter more than technology.
• How the real upside of AI is giving people more space for imagination, empathy, and meaningful human connection.
• How to prepare students and professionals for an AI-shaped job market by prioritizing learning paths, adaptability, and relationships over fixed career tracks.
• Why the biggest risks of AI come from small, hard-to-detect changes in data or models that can create serious downstream harm.
• How AI is pushing education, work, and leadership back toward core human skills like judgment, curiosity, and imagination.
• Where cautious optimism comes from, including AI’s potential to expand access to knowledge, healthcare, and opportunity when used with care.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Lynn on LinkedIn
• AI fun fact article
• On How genAI studios launch AI-first companies

Other podcast episodes mentioned on the show:

• On reinventing the academic curriculum for MBAs with Dave Marchick, Dean of the Kogod School of Business
• From 3 Takeaways:
  • The Genetic Revolution Has Begun – George Church on What Comes Next
  • The Transforming Power of Hospitality in Business: Setting the Table with Union Square Hospitality Group Founder & CEO Danny Meyer

Amit Bendov is the co-founder and CEO of Gong, the revenue AI platform he started in 2015 after realizing that traditional CRM systems tracked outcomes but failed to explain why deals were won or lost. That insight led him to focus on customer conversations as the missing source of truth in sales. Since its founding, Gong has raised more than $580 million and reached a valuation of $7.25 billion. Today, Gong helps sales teams reduce manual work, improve performance, and better understand what customers are actually saying.

In this conversation, we discuss:

• Why traditional CRM systems track what happened but fail to explain why deals are won or lost, and how that gap led to the rise of Revenue AI as a new category.
• How Gong’s Revenue AI differs from CRM by analyzing sales conversations, reducing manual admin work, and actively helping sellers prepare, follow up, and improve performance in real time.
• The emotional cost of sales work, and how using AI to remove administrative burden improves both sales results and seller job satisfaction.
• What it takes to build trust in AI tools that analyze customer conversations, including data stewardship, transparency, and delivering clear value to sellers.
• How an AI-first product vision can exist years before the technology is ready, and what it means to design systems for autonomy rather than simple automation.
• The reality behind “overnight success,” including early product-market fit tests, paid pilots that felt risky, and navigating growth slowdowns without abandoning the original vision.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Amit on LinkedIn
• AI fun fact article
• On How AI Is Changing Finance: Data Challenges, Collaboration, and Future Trends with Mike Schuster
• Other episode mentioned in the show:
  • On AI Design Philosophy and Building the Anti-PowerPoint with Grant Lee, CEO of Gamma 

Kimberly Williams is CEO of Absorb Software, where she helps over 3,000 organizations deliver smarter learning experiences to 34 million employees. She brings decades of leadership in enterprise tech and now sits at the center of how AI is changing the way people grow at work. In this episode, Kimberly shares how learning becomes more powerful when it’s personalized, embedded in daily workflows, and led by curious teams who treat culture as a competitive advantage.

In this conversation, we discuss:

• How AI is shifting corporate learning from generic training programs to personalized, in-the-flow development tailored to each employee’s needs.
• Why in-context learning matters more than traditional courses, and how AI coaching inside tools like Slack, Salesforce, or ServiceNow changes how people actually learn at work.
• What it means to turn L&D teams into AI model trainers who encode company culture, values, and knowledge into coaching experiences.
• How Absorb Software tracks AI usage across teams and uses dashboards and leaderboards to drive internal adoption.
• The role of outcome data in modern learning systems, and how tying learning directly to performance metrics changes what training gets delivered.
• The advice Kimberly gives early-career talent, especially women, about finding roles where their contributions are measurable and their growth is supported by culture, not just credentials.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kimberly on LinkedIn
• AI fun fact article
• On how Robert Plotkin addresses LLM regulation and legal advice for entrepreneurs
• Other episodes mentioned on the show:
  • AI as a Liberating Technology: Josh Bersin on Turning Routine Tasks into Superworkers Driving Trust, Creativity, and Growth
  • Dr. John Boudreau, future of work pioneer and former Cornell professor, discusses the new definition of work

In this special episode of AI and the Future of Work, host Dan Turchin looks back on what 365 conversations have revealed about how AI is reshaping the way we work.

What themes have emerged most consistently? Which ideas connect founders, researchers, and operators across industries? And what have these discussions taught us about the evolving relationship between humans and intelligent systems?

Featuring Guests:

1. Mark McCrindle, Founder and Principal at McCrindle  – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13014260
2. Pradeep Menon, CTO at Microsoft – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13034974
3. Dave Kellogg, EIR at Balderton Capital – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16665133
4. Alex Buder Shapiro, Chief People Officer at Jasper AI – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17522593
5. Gary F. Bengier, Writer, philosopher, and technologist – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/12934217
6. Josh Bersin, Founder and CEO at The Josh Bersin Company – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17863187
7. Bryan Power, Head of People at Nextdoor – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16837259
8. Dave Treat, Chief Technology Officer at Pearson – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17557154

💡 What You Will Learn

• Why the future of work remains human-centered
• How AI amplifies human capability rather than replacing it
• Why trust and transparency define successful AI-driven teams
• How workplace culture is evolving as organizations adopt AI
• Why meaning, empathy, and lifelong learning matter more than ever

💬 Inspired by this episode?

Share your favorite insight on social media and tag us (https://www.instagram.com/aifutureofwork/)
And remember to subscribe for more conversations with the leaders shaping the future of AI and work.

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)

Henrik Werdelin is a founder and investor who has spent more than a decade building companies at the intersection of culture, technology, and consumer behavior. He co-founded BARK, the public company that redefined how millions of dog parents connect with their pets, and Prehype, the startup studio behind brands like Ro and Audos.

In this episode, Henrik explores how founders can embrace AI without losing human connection, drawing from his experience as co-host of Beyond the Prompt and co-author of Me, My Customer and AI.

Recognized by Fast Company and Business Insider for his creative impact, Henrik shares a practical perspective on building companies that scale while staying deeply human.

In this conversation, we discuss:

• Why Henrik believes founders must stay close to users and how AI can deepen (not dilute) human connection.
• What “building companies at the edge of culture” means and why authenticity beats scale when designing for trust.
• How Henrik and his team use AI to speed up product development without compromising on creativity or purpose.
• The shift from storytelling to “storylistening” and how paying attention to customer behavior shapes better products.
• What the best founders get wrong about generative AI and why Henrik advocates for a more mindful approach to adoption.
• How roles inside companies are evolving in response to AI and what leaders can do to support creative experimentation.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Henrik on LinkedIn
• AI fun fact article
• How to Use Generative AI to Get Ahead In Your Career

Kelly Jones is Chief People Officer at Cisco, where she leads the people strategy for more than 84,000 employees worldwide. Over nearly two decades, she has helped make Cisco a global benchmark for workplace culture. In this episode, Kelly explains why trust is the foundation of every AI strategy, how Cisco is equipping managers for an era of augmented work, and what it takes to lead responsibly when the pace of change is this fast.

In this conversation, we discuss:

• Why trust is Cisco’s most valuable workplace currency and how it shapes decisions about AI, culture, and leadership.
• How AI becomes a co-pilot when employees are given the safety, training, and time to explore new tools at their own pace.
• What “super leadership” looks like and the four traits Cisco’s CPO believes will define successful managers in an AI-augmented workplace.
• How Cisco evaluates AI use cases based on disruption, scale, and their potential to enhance the employee experience.
• Why the real opportunity of AI lies in automating administrative work to give humans more time for purpose, creativity, and connection.
• The systems Cisco is building to ensure responsible AI use through governance, upskilling, and clear ethical boundaries.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kelly Jones on LinkedIn
• AI fun fact article
• On How to Use Generative AI to Get Ahead In Your Career
• Other episode mentioned in the show: AI as a Liberating Technology: Josh Bersin on Turning Routine Tasks into Superworkers Driving Trust, Creativity, and Growth

Eric Cheng is co-founder and CEO of Jobright, the AI career copilot serving more than 550,000 users. After building core backend systems at Box and scaling Fangcloud to acquisition, he turned his focus to fixing what’s broken in hiring. His perspective blends engineering depth with a human-centered approach to matching talent and opportunity.

In this conversation we discussed:

• Why Eric created Jobright after interviewing 150 young professionals and discovering a gap in personalized job search support.
• How Jobright reframes hiring as a “matching” problem and uses AI to function more like a career coach than a job board.
• The limitations of keyword-based search tools and how AI enables more nuanced, human-like job matching.
• Why building trust matters in AI-powered hiring platforms and how Jobright balances efficiency with authenticity and accuracy.
• What the “learning loop” means for job seekers and why Eric believes the mindset shift matters more than the résumé.
• How emerging roles like AI operations and forward deployment engineers reflect deeper changes in how organizations adopt and manage AI.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Eric Cheng on LinkedIn
• AI fun fact article
• On How to raise over $200 million to detect audio deepfakes

Kate O’Neill is a leading voice on AI and tech humanism, known for helping organizations build more meaningful, human-centered futures. She has been featured by outlets like BBC, NPR, and NBC, and serves on the United Nations AI advisory board. A CX Hall of Fame inductee and award-winning entrepreneur, Kate brings a unique blend of optimism and realism to conversations about AI, data, and the future of work. Her latest book, What Matters Next, explores how to make human-friendly tech decisions.

In this conversation we discussed:

• How tech humanism explains the relationship between people, technology, and business, and how leaders can design AI systems that strengthen the alignment
• Why humans project intelligence and agency onto AI tools, and what it takes to build healthy, intentional habits around emerging technologies
• Practical ways workers can use AI to elevate their roles rather than fear automation
• The role of leadership in creating psychologically safe environments where employees can openly experiment with AI tools
• The risk of designing systems that lead to “automated bureaucracy,” and how organizations can embed meaning into automated experiences at scale
• Why meaning and purpose remain uniquely human, and how future workplaces can evolve by pairing human judgment with increasingly capable AI systems

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kate on LinkedIn or at KO Insights
• AI fun fact article
• On How Unleashing Human Potential with AI

Sid Sheth is the CEO and co-founder of d-Matrix, the AI chip company making inference efficient and scalable for datacenters. Backed by Microsoft and with $160M raised, Sid shares why rethinking infrastructure is critical to AI’s future and how a decade in semiconductors prepared him for this moment.

In this conversation, we discuss:

• Why Sid believes AI inference is the biggest computing opportunity of our lifetime and how it will drive the next productivity boom
• The real reason smaller, more efficient models are unlocking the era of inference and what that means for AI adoption at scale
• Why cost, time, and energy are the core constraints of inference, and how D-Matrix is building for performance without compromise
• How the rise of reasoning models and agentic AI shifts demand from generic tasks to abstract problem-solving
• The workforce challenge no one talks about: why talent shortages, not tech limitations, may slow down the AI revolution
• How Sid’s background in semiconductors prepared him to recognize the platform shift toward AI and take the leap into building D-Matrix

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Sid on LinkedIn
• AI fun fact article
• On Mastering Skills To Stay Relevant In the Age of AI

Darrick Horton is the CEO and co-founder of TensorWave, the company making waves in AI infrastructure by building high-performance compute on AMD chips. In 2023, he and his team took the unconventional path of bypassing Nvidia, a bold bet that has since paid off with nearly $150 million raised from Magnetar, AMD Ventures, Prosperity7, and others. TensorWave is now operating a dedicated training cluster of around 8,000 AMD Instinct MI325X GPUs and has already hit a $100 million revenue run rate.

Darrick is a serial entrepreneur with a track record of building infrastructure companies. Before TensorWave, he co-founded VMAccel, sold Lets Rolo to LifeKey, and co-founded the crypto mining company VaultMiner.

He began his career as a mechanical engineer and plasma physicist at Lockheed Martin’s Skunk Works, where he worked on nuclear fusion energy. While he studied physics and mechanical engineering at Andrews University, he left early to pursue entrepreneurship and hasn’t looked back since.

In this conversation we discussed:

• Why Darrick chose AMD over Nvidia to build TensorWave’s AI infrastructure, and how that decision created a competitive advantage in a GPU-constrained market
• What makes training clusters more versatile than inference clusters, and why TensorWave focused on the former to meet broader customer needs
• How Neocloud providers like TensorWave can move faster and innovate more effectively than legacy hyperscalers in deploying next-generation AI infrastructure
• Why power, not GPUs, is becoming the biggest constraint in scaling AI workloads, and how data center architecture must evolve to address it
• Why Darrick predicts AI architectures will continue to evolve beyond transformers, creating constant shifts in compute demand
• How massive increases in model complexity are accelerating the need for green energy, tighter feedback loops, and seamless integration of compute into AI workflows

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Darrick on LinkedIn
• AI fun fact article
• On How the new definition of work

Grant Lee is the CEO and co-founder of Gamma, the company reimagining presentations by building what some call the “anti-PowerPoint.” Since launching in 2022, Gamma has grown to 50 million users and reached $50M in annual recurring revenue. These milestones were achieved with just $12M in venture capital and a 30-person team. Before founding Gamma in 2020, Grant led finance at Optimizely, where he developed a passion for A/B testing. He began his career in investment banking and holds a BS in Biomechanical Engineering and an MS in Mechanical Engineering from Stanford University.

In this conversation, we discuss:

• How Gamma went from an idea to one of the fastest-growing presentation tools in the world with $50M ARR and a 30-person team
• Why Grant and his co-founders set out to reinvent slides from scratch instead of improving on PowerPoint
• Lessons from Optimizely that shaped Gamma’s culture of experimentation and rapid iteration
• How Grant thinks about product-market fit and why every feature must solve real user pain instead of mimicking the competition
• How AI serves as a design partner, not a replacement for human creativity, and why “human in the loop” is central to Gamma’s philosophy
• The importance of building user trust in generative AI through transparency, feedback loops, and community programs like the “Gambassador” initiative
• How resilience, early failures, and conviction helped Gamma survive investor rejection and a near-collapse during the SVB crisis

Dennis Kozak is the CEO of Ivanti, a leading enterprise IT and security company generating over $1 billion in annual revenue and serving more than 40,000 customers. He previously served as Ivanti’s COO after holding senior leadership roles at Avaya. Earlier in his career, Dennis spent nearly 23 years at CA Software (now Broadcom), where he led global partnership sales and services teams. He holds a BS in Accounting from St. Joseph’s University in Long Island.

In this conversation, we discuss:

• Dennis’s leadership journey from CA Technologies and Avaya to becoming CEO of Ivanti, and what prepared him to lead a billion-dollar IT security company
• Why convergence between cybersecurity and IT operations is accelerating, and how Ivanti is positioning itself at the center of that shift
• The impact of generative AI on IT support, including how Ivanti is building AI agents to handle routine tickets and empower human technicians
• How organizations can reduce cyber risk by closing visibility gaps and simplifying their tech stack
• The challenges of securing distributed workforces in a hybrid world, and why automation is critical to stay ahead of threats
• Why Dennis believes the future of enterprise IT is about blending user experience with security, not choosing between them

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Dennis on LinkedIn
• AI fun fact article
• On How to Reimagine Fan Experiences and Digital Transformation.

Jim Curry is the co-founder and CEO of BuildGroup, a venture firm based in Austin that has raised $330 million since its founding in 2015 and backed companies like Anaconda, Vidmob, DigniFi, and Benefitfocus. He brings more than two decades of experience in product, strategy, and corporate development from roles at Rackspace and Dell, and he co-founded OpenStack, one of the most widely used open source cloud computing platforms. Jim serves on the boards of Generation Serve and the University of Texas School of Undergraduate Studies. He holds degrees from UT Austin and Harvard Business School.

In this conversation, we discuss:

• Jim’s journey from Rackspace to launching BuildGroup and why he believes in “longer, slower capital” to support mission-driven founders
• How his experience co-founding OpenStack shaped his thinking on community-driven innovation and open-source software
• What AI startups can learn from the cloud era—and why infrastructure still matters in the age of foundation models
• Why Jim believes VCs often push startups to scale too fast and what sustainable growth looks like in practice
• The impact of AI on venture capital and how BuildGroup thinks about investing in software companies that solve real problems
• How founders can balance product vision with pragmatism, especially when building in volatile markets

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Jim on LinkedIn
• AI fun fact article
• On How to Develop NLP and AI Data Harvesting Using Games and Blockchains To Earn NFTs