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

James Cham, Partner at Bloomberg Beta and long‑time AI infrastructure investor with a CS and MIT MBA background, challenges common assumptions about responsibility and humans in decision loops. He argues for assigning moral and legal accountability to beneficiaries of models. Short takes cover model consistency versus human unpredictability, why removing humans from certain loops can be better, and three big AI investment opportunities.

Adrian McDermott, CTO at Zendesk who scaled its product and engineering teams, shares how customer service became strategic. He talks about practical AI for agents, balancing automation with human touch. He explains the move from creative to deterministic AI, the rise of context engineering, and building systems that capture knowledge from every interaction.

Tess Posner, founder of AI4ALL expanding AI access; Mona Sabet, SVP focused on skill-based hiring; Patty Hatter, Opsera COO urging risk over perfection; Daphne Jones, board leader navigating bias and imposter syndrome. They discuss taking risks before feeling perfect. They cover beating imposter syndrome, escaping perfectionism, fixing brand-driven hiring, and diversifying who builds AI.

Matt Britton, Founder and CEO of Suzy and author of Generation AI, studies generational change and AI’s business impact. He discusses how AI shifts value from memorized knowledge to creative problem solving. He covers reskilling challenges, Gen Alpha’s AI-native expectations, robotics disrupting service jobs, and why companies should solve core problems before chasing tools.

Kourtney Cross, a RiseUp with ServiceNow graduate and Business Analyst at Leidos who moved from accounting into enterprise tech, describes his reskilling journey. He talks about earning certifications, building public hands-on projects to prove skills, using AI daily to write user stories and tighten requirements, and where human judgment must remain in high-stakes decisions.

Scott Strickland, Chief Commercial Officer at Wyndham Hotels & Resorts and former CIO, brings enterprise tech and AI leadership experience. He discusses aligning AI to business ROI and time-to-value. He explains winning board support with the “4 E’s,” scaling from a few pilots to hundreds of use cases, balancing automation with hospitality, and building trust through transparency, reskilling, and security-by-design.

George Sivulka, Hebbia CEO and former Stanford researcher, focuses on turning meta-learning into document solutions. Daniel Marcous, April founder and ex-Waze CTO, builds rigorously tested infrastructure for sensitive data. Dmitry Shapiro, MindStudio CEO and veteran entrepreneur, explores human–machine interaction and privacy. Rich White, serial entrepreneur and Fathom CEO, emphasizes solving real pain and strong user research. Eric Olson, Consensus co-founder and former athlete, talks about launching amid uncertainty.

Andrea Iorio, author and former digital leader at Tinder and L’Oréal Brazil, explores how AI automates tasks while human skills become crucial. He highlights HR’s shift to soft skills, outlines three pillars of transformation with nine key skills, and explains why better questions, reverse mentoring, and human responsibility matter as autonomous AI agents rise.

Lynne Chou O’Keefe, founder of Define Ventures and early healthtech investor, talks about why fragmented systems make AI most useful in admin and workflows. She outlines three AI adoption phases, explores ethics and human-in-the-loop safeguards, and explains how value-based care and consumer expectations reshape healthcare delivery.

Dave Kellogg, serial SaaS CEO and investor known for Kellblog, shares sharp takes on enterprise software and go-to-market strategy. He explains how people now work for algorithms, why SaaS is under pressure but not dead, how AI pushes work up the value chain and creates new roles, and why trust is rising as the most valuable currency in an age of AI-driven low-quality content.