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

George Maddaloni is the EVP and CTO for Operations at Mastercard, where he leads the performance and modernization of technology platforms serving more than 35,000 employees worldwide. He has previously held senior IT leadership roles at AIG, UBS, AT&T, GM, and Merrill Lynch, and currently serves on the board of SustainableIT.org. George earned his BS in Mechanical Engineering and Computer Science from Johns Hopkins University and an MBA from Fordham University.

In this conversation, we discuss:

• How Mastercard’s CTO thinks about the balance between innovation, trust, and regulation in one of the world’s most complex financial networks.
• The strategy behind modernizing Mastercard’s internal technology platforms to empower 35,000 global employees.
• Why a decade of AI experience changed how Mastercard approaches fraud, data, and customer confidence.
• The cultural shift that turned curiosity about AI into measurable progress across a global workforce.
• How a 50-year-old payments company keeps competing with startups by rethinking infrastructure from the ground up.
• George Maddaloni’s vision of the next era of payments and how technology might make transactions faster, safer, and nearly invisible.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with George on LinkedIn
• AI fun fact article
• On How To Create an Energy-Based Work System that Empowers Employees
• Other resources mentioned in this conversation: On decentralized AI in Banks and the Future of Finance with Paolo Ardoino, Tether CEO 

Jon Levy is a behavioral scientist and New York Times bestselling author known for exploring trust, human connection, belonging, and influence. He’s the founder of The Influencers Dinner, a secret dining experience that has grown into a community of thousands of leaders, including Nobel laureates, Olympians, celebrities, executives, artists, and musicians. His book You’re Invited: The Art and Science of Connection, Trust, and Belonging was named a Wall Street Journal “Book of the Month” in 2021. He’s also the author of The 2 AM Principle: Discover the Science of Adventure and the newly released Team Intelligence: How Brilliant Leaders Unlock Collective Genius.

In this conversation, we discuss:

• Why the smartest teams often fail, and how trust, belonging, and psychological safety drive collective intelligence
• The surprising data behind team performance, including why individual IQ doesn’t predict group success
• What makes a team “brilliant,” and how leaders can design environments that unlock group flow and faster decision-making
• How AI changes team dynamics and why it’s urgent to redefine collaboration in a hybrid, tech-driven world
• The four principles of Team Intelligence and how they apply to both startups and global enterprises
• Jon’s personal journey from hosting secret dinners to writing Team Intelligence, and why he believes social bonds are the future of work

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Learn more of Jon on LinkedIn
• Explore Jon’s published work and speaking events
• AI fun fact article
• On How gen AI startups can beat Big Tech incumbents

Tracy Layney is a seasoned HR leader with more than 15 years of experience shaping people and culture strategies at Levi’s, Gap, and Shutterfly. She currently teaches Human Capital Strategy as an adjunct professor at the University of Chicago Booth School of Business. Tracy holds a BA in English from the University of Pennsylvania.

In this conversation, we discuss:

• Tracy shares her unconventional path from English major and aspiring lawyer to CHRO at Levi’s, Gap, and Shutterfly, and how consulting shaped her approach to organizational strategy.
• She reflects on lessons from working with iconic leaders like Eva Sage Gavin and Chip Bergh, including leading Levi’s through the early days of the pandemic.
• She explains why excellence and heart-centered leadership must coexist to build values-driven, high-performing cultures.
• She explores how AI and other disruptive forces are reshaping HR, from talent strategy to employee expectations, and why adaptability is critical for leaders.
• She discusses the importance of transparency and trust-building between HR and employees during times of uncertainty, drawing parallels with past crises.
• She shares her perspective as a professor on how future HR leaders are navigating unprecedented change, mental health challenges, and the rapid rise of AI in the workplace.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Tracy on LinkedIn
• AI fun fact article
• On How To Democratize Content Creation using AI 

Sean Williams is the CEO and founder of AutogenAI, the world’s leading AI proposal-writing engine, launched in May 2022. Under his leadership, the company recently closed a nearly $40 million Series B round led by Salesforce Ventures. Prior to AutogenAI, Sean founded Corndel Ltd, where he served as Chief Executive and scaled the business to 350 employees before its $60 million acquisition by THI Holdings in 2020.

In this conversation, we discuss:

• Why Sean believes AI will revolutionize how organizations write, win, and deliver proposals
• How AutogenAI is reducing proposal writing time from days to hours for companies bidding on complex contracts
• The ethical considerations of AI-written proposals and why transparency is critical in high-stakes industries
• What Sean learned from scaling Corndel to 350 employees and how that experience shaped AutogenAI’s go-to-market strategy
• Why the biggest risk for organizations isn’t adopting AI too quickly, but failing to experiment early
• How AutogenAI is building trust with enterprise clients through customization, compliance, and human-in-the-loop design

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Sean on LinkedIn
• AI fun fact article
• On How To Prevent Bias and Be Responsible for Ethical Decision Making’s

Josh Bersin is one of the most respected voices in HR and HRTech, known for shaping how organizations think about talent, learning, and the future of work. He began covering the space in 2001 and later sold his firm, Bersin & Associates, to Deloitte in 2012. Today, he leads The Josh Bersin Company, which produces influential research, publishes widely on workplace trends, and hosts the annual Irresistible conference. He’s also the author of Irresistible: The Seven Secrets of the World’s Most Enduring, Employee-Focused Organizations and the host of a podcast that explores the evolving world of work with clarity and insight.

In this conversation, we discuss:

• Why fears of AI-driven job loss are overstated and how automation can unlock new opportunities for growth.
• The rise of “superworkers” who use AI to eliminate routine tasks and focus on creativity, innovation, and more meaningful contributions.
• How companies are rethinking organizational design, roles, and skills in response to rapid advances in AI.
• Real-world examples of AI adoption in banking, insurance, and airlines—and what leaders can learn from them.
• The concept of “supermanagers” and why human leadership and soft skills remain critical in an AI-powered workplace.
• Josh’s perspective on what it means to be an “irresistible organization” in a time of massive technological and cultural change.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Josh on LinkedIn
• AI fun fact article
• On How To Invest on AI Driven Work
• Past Episode with Josh [Season 3, #278]: On How the Best-Performing Teams use AI

Jody Glidden is the CEO and founder of Postilize, a company focused on reinventing CRM through AI. Before launching Postilize, he co-founded Introhive and served as CEO until 2022, helping raise over $100 million to build the enterprise relationship management category. A serial entrepreneur, Jody previously founded icGlobal, which was acquired by Smartforce, and played a key role in scaling Chalk Media, later acquired by BlackBerry maker Research in Motion. He holds a BBA from the University of New Brunswick and a Master’s in Information Systems from Harvard.

In this conversation, we discuss:

• Why traditional CRMs fail to reflect how relationships actually evolve—and how Postilize is addressing that gap
• How Postilize handles privacy, hallucinations, and human oversight to stay useful without crossing ethical lines
• Jody’s approach to using AI not to replace human connection, but to augment and scale authentic relationship building
• How relationship intelligence helps sales and go-to-market teams understand who to engage, when, and why
• Why keeping CRMs accurate is nearly impossible without automation and real-time enrichment
• What Jody learned from building Introhive and why Postilize is taking a radically different approach
• The future of CRM as a system of engagement rather than just a system of record

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Jody on LinkedIn
• AI fun fact article
• On How To Manage Enterprise Apps That Support Thousands of Employees for a Rapidly Growing Global Company.

Anthony Moisant is the Chief Information Officer (CIO) and Chief Security Officer (CSO)  at Indeed, the world’s leading job site with over 610 million job seeker profiles. He joined Indeed nearly five years ago after serving in a similar role at sister company Glassdoor for eight years. As CIO, he leads the teams responsible for the internal technology that supports employees and drives the business. As CSO, he oversees the security team focused on protecting the data of job seekers, customers, and employees. Anthony is also a graduate of the U.S. Navy Nuclear Submarine School.

In this conversation, we discuss:

• Indeed’s goal to cut time-to-hire by 50% by removing friction across systems and workflows.
• Solving the hiring resume glut so every application gets seen and answered, using AI to improve matching and follow-ups.
• Why skills (not degrees) will define the future of hiring, and how job seekers can prepare for a skill-first economy
• How to double team productivity with AI while keeping trust high and addressing fears about automation.
• A values-driven approach to AI ethics: transparency, fairness testing, red-teaming models, and an “AI constitution” agent.
• The lessons Anthony brought from the U.S. Navy and how they continue to shape his leadership approach in high-pressure environments

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Anthony on LinkedIn
• AI fun fact article
• On How to Invest and Advise Early Stage Tech Companies

A few days ago, Nick Mehta announced his transition from CEO to Board Director and Special Advisor at Gainsight. As CEO, he spent more than a decade transforming the company into a global leader in customer success, serving over 20,000 customers and surpassing $100 million in ARR. Before Gainsight, he led LiveOffice through its acquisition by Symantec and co-founded Chipshot in the 90s. Nick serves on the boards of F5 and PubMatic and holds a Bachelor’s degree in Biochemistry and a Master’s degree in Computer Science, both from Harvard. Known for leading with heart, humor, and humility, he’s also the voice behind the blog Mehtaphysical Musings, a rapper, and a YouTube creator with over 50 parody videos.

In this conversation, we discuss:

• How Nick Mehta balances vulnerability and optimism as a leader navigating uncertainty
• Why Gainsight’s values like “childlike joy” matter more in an AI-driven world
• What happens to identity and purpose in a post-work economy shaped by automation
• The growing divide between capital and labor, and why Marxist ideas are resurfacing in the AI era
• Why we shouldn’t assume past tech cycles will repeat and how to question AI’s impact on jobs
• What Gainsight’s AI initiative “Atlas” reveals about the rise of agentic tech in customer success

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Nick on LinkedIn
• Past Episode with Nick [Season 5, #298]: On Building A Human-First AI Culture
• Watch this for a laugh: “I promise that you’ll never find a CEO like Nick”
• Recommended by Nick:
  • Three-Body Problem by Liu Cixin
  • Player Piano by Kurt Vonnegut

Dr. Jad Tarifi is the co-founder of Integral AI, a company he launched in 2021 after holding senior AI roles at Google. He earned his PhD in Computer Science and AI from the University of Florida and completed his undergraduate studies at the University of Waterloo. A returning guest to the podcast, Jad is a leading thinker on world models in AI and often shares insights on the science of longevity and the future of intelligence.

In this conversation, we discuss:

• Why Jad believes the goal of AGI isn’t intelligence but freedom, and how that redefinition reframes both ethics and alignment
• The role of world models in achieving AGI, and why video prediction alone isn’t enough for robust, reliable reasoning
• What it means to design AI that can autonomously learn new skills with minimal energy and data, matching or exceeding human learning efficiency
• How Integral AI is building AGI-capable models by focusing on unsupervised abstraction and embodied, open-ended agents
• How Jad defines superintelligence and what it reveals about the evolving relationship between humans and machines
• A glimpse into Integral’s long-term roadmap, including recursive superfactories and post-AGI economies

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Jad on LinkedIn
• AI fun fact article
• On How To Pick The Right Business Problem to Solve with AI
• Jad Tarifi’s past episode on how to train AI to reason like humans

William Chan is the co-founder and CEO of Iodine Software, a company he helped launch in 2010 to pioneer the use of AI in helping healthcare providers get paid. A serial entrepreneur, he previously co-founded WhisperWire, acquired by Convergys, and Crimson, acquired by The Advisory Board, and has held product leadership roles at companies including Oracle. William holds a BS in computer science from Cornell University and an MBA from Harvard Business School.

In this conversation, we discuss:

• The challenges hospitals face in accurately capturing patient care details for proper reimbursement.
• How AI can address staffing shortages by assisting with clinical documentation review.
• The importance of responsible AI that supports, rather than replaces, human decision-making in healthcare.
• Strategies to reduce bias and improve accuracy by training AI models on diverse datasets from different hospital types and geographies.
• Why AI must deliver clear, actionable insights that clinicians can validate, ensuring trust and accountability in healthcare decisions.
• William’s vision for reducing the $260 billion in administrative waste and enabling providers to focus more on patient care.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with William on LinkedIn
• AI fun fact article
• On How To Revolutionizing Finance and Decision-Making
• Past episodes mentioned in this conversation:
  • [With Dr. Shiv Rao, CEO and Co-Founder of Abridge] – On How Generative AI is fixing the Biggest Problem faced by Doctors

Dr. Mark van Rijmenam is ranked among the world’s best futurists and is known globally for his trademark “Optimistic Dystopian” viewpoint. Recognized by Salesforce as a top voice shaping the future of AI, he’s a sought-after speaker on the relationship between innovation and humanity. He delivered the world’s first TEDx Talk in VR (2020) and introduced a digital twin that speaks 29 languages (2024). Mark holds a PhD in Management from the University of Technology Sydney, where he studied how organizations can use big data, blockchain, and AI. He’s also a six-time author and dedicated endurance athlete.

In this conversation, we discuss:

• Why Dr. Mark van Rijmenam believes we need a paradigm shift to prepare society for the long-term consequences of AI and quantum computing
• The critical difference between building technology for shareholders versus stakeholders and how that shapes our future
• What the “spiral dynamics” framework reveals about humanity’s current worldview and its path toward a more interconnected mindset
• How banning technology for kids under 16 could protect future generations and reshape digital education
• The risks of anthropomorphizing AI and the need to preserve human agency in a world increasingly shaped by machines
• What inspired Dr. Mark’s sixth book Now What? and how he uses fiction, philosophy, and global cultures to help readers ride the tsunami of change

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Mark on LinkedIn
• AI fun fact article
• On Extending Life With AI
• Explore more from Dr. Mark van Rijmenam:
  • Now What? How to Ride the Tsunami of Change
  • Dr. Mark’s TEDx Talk in VR
  • His multilingual digital twin

Dave Treat is the Chief Technology Officer of Pearson, the world’s largest education company headquartered in London, with a market cap of $11 billion and over 17,000 employees. Before joining Pearson, he spent several years at Accenture as a Senior Managing Director leading the Innovation Incubation Group. Dave has also served on multiple technology and industry boards, including the Linux Hyperledger Foundation, Linux Open Wallet Foundation, Digital Dollar Project, and the Global Business Blockchain Council. Earlier in his career, he held leadership roles at Deloitte and UBS. He holds a master’s degree in Higher Education Administration from the University of Michigan and a degree in Psychology from the University of Pennsylvania.

In this conversation, we discuss:

• How Pearson is evolving from a textbook publisher into a software company driving the future of learning
• Why AI study tools are reshaping when and how students learn, meeting them at the exact moment they need help
• The mental health and motivation challenges students face today, and how AI can support them with simpler, more personalized learning
• How AI can simplify the administrative burden for educators and free them to focus on deeper student engagement
• Why the traditional “slingshot model” of education is broken and how skill mapping and lifelong learning are the future
  How immersive, 3D digital learning experiences will replace today’s flat, two-dimensional interactions

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Dave on LinkedIn
• AI fun fact article
• On leveraging AI to create more time in your day
• Other resources mentioned in this conversation:
  • [With Dave Marchick, Dean of the Kogod School of Business] – On How AI is Changing Academia
  • Lost in Transition: Fixing the “Learn to Earn” Skills Gap

Alex Buder Shapiro is the Chief People Officer at Jasper AI, a company with more than 100,000 customers using its AI-first marketing platform and over $125M raised. She is a forward-thinking people leader with a unique perspective on the role of HR and the future of teams, having served in the same position for six years at Flatiron Health and as an HR Business Partner Manager for nearly eight years at Google. Alex studied Political Psychology and Theatre Arts at the University of Pennsylvania.

In this conversation, we discuss:

• How Alex’s early career at Google shaped her views on aligned incentives, experimentation, and building high-performing people cultures.
• Why the employer and employee relationship has shifted dramatically in the last five years, from shared incentives to trade-offs driven by economic and social change.
• Why AI adoption in the workplace creates both opportunities and anxieties, and how people leaders can design human-centered approaches to integrating AI.
• The concept of “practicing at the top of your license” and how it applies to redesigning work in an AI-driven future.
• How the next generation of employees will challenge and reshape workplace structures through their fluency with AI and new ways of learning, mentorship, and problem solving.
• What responsible AI means for people leaders, including addressing bias, conscious adoption, and collective accountability.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Alex on LinkedIn
• AI fun fact article
• On How To Build High Performance Organization with AI for the Tech Services
• Past episodes mentioned in this conversation:
  • [With Dave Marchick, Dean of the Kogod School of Business] – On How AI is Changing Academia
  • [Bryan Power, Nextdoor’s Head of People] – On how AI is Reshaping Work and Job Loyalty

Paolo Ardoino is the CEO of Tether, the company behind the ticker symbol USDT, the world’s largest stablecoin. He also serves as CTO of the cryptocurrency exchange Bitfinex and co-founded Holepunch, a platform for peer-to-peer applications. Ardoino holds a Master’s in Computer Science from the University of Genoa and is one of the most visible proponents of improving the banking system with cryptocurrencies.

In this conversation, we discuss:

• How Paolo built the infrastructure behind the world’s most used stablecoin and why he believes math, not politics, should govern money
• Why he believes Bitcoin is the first form of money governed by math, and how that math could reshape global finance
• How USDT became the most used digital dollar by solving practical challenges in regions with limited banking access
• Why Paolo believes traditional finance is broken and how decentralized tech offers a more inclusive infrastructure
• The case for brain–computer interfaces and why Paolo sees human and AI symbiosis as the next frontier of intelligence
• Why he’s optimistic about AI’s role in society, even as he argues that long term AI safety might be an illusion

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Paolo on LinkedIn or on X
• AI fun fact article
• On How to Ensure the AI and Workplace Technologies Align with Civil Rights Laws

Kyle Daigle is the Chief Operating Officer at GitHub, the world’s largest host of source code with more than 100 million developers and 420 million repositories. He joined GitHub in 2013 and later served as VP of Strategy and Chief of Staff to the CEO, playing a key role in the company’s 2018 acquisition by Microsoft. Kyle is also the public face of GitHub Copilot, the AI coding assistant launched in 2021 that now helps over 15 million users. Earlier in his career, he was a partner at Digitalworkbox and VP of Product Development at Geezeo.

In this conversation, we discuss:

• Kyle’s journey from studying fine arts to leading operations at the world’s largest code platform
• Why GitHub Copilot is about freeing developers to focus on creativity and solving meaningful problems
• What it means to bring pragmatism into AI development and why usefulness always wins over hype
• How AI is lowering the barriers to software creation while keeping humans at the center of accountability
• The responsibility of platforms like GitHub to protect users from flawed code and teach safe coding by design
• Kyle’s vision for “ambient AI” and why the future should feel personal, context-aware, and privacy-conscious

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kyle on LinkedIn
• AI fun fact article
• On How to Discuss Regulation for LLMs and Legal Advice for Entrepreneurs
• Past episodes mentioned in this conversation: [With Patty Hatter, tech exec/board member/advisor] – On the best advice for women in technology