Crisis Leadership, AI, & Team Trust &: A 400-Person Decision | Jed Ayres, CEO & Gadi Feldman, CPO

ControlUp CEO Jed Ayres made a decision few leaders would consider: bring 400 employees to Dubai while the company was operating through war and crisis. In this episode, Ayres and ControlUp Chief Product Officer Gadi Feldman explain what happened afterward—and why AI may create the next leadership test. The conversation begins with a problem few executives are prepared for: how do you reunify a distributed team when people are operating through fear, uncertainty, and physical separation? Jed and Gadi share the reasoning behind bringing 400 employees together in Dubai, the change they saw in morale and connection, and why physical presence mattered when another video call could not solve the problem. Then the conversation turns to the future of work. If AI automates support, changes roles, and removes layers from the organization, what must leaders protect? How do you use data to improve employee experience without losing the trust that makes change possible? Watch to hear the story behind the Dubai decision—and what these two ControlUp leaders believe organizations need to prepare for next. IN THIS CONVERSATION • How leaders make decisions during war and crisis • Why 400 employees were brought together in Dubai • What changed when distributed teams met in person • How flatter organizations affect trust and accountability • Where AI can improve employee experience and support • How AI may reshape jobs, roles, and organizational structure CHAPTERS 00:00 Introduction to Jed Ayres and Gadi Feldman 08:33 Leading during war and crisis 11:03 The decision to fly 400 employees to Dubai 12:57 Unifying dispersed teams across countries 15:07 Building trust through physical presence and culture 17:05 Moving from hierarchical to flat organizations 19:00 Balancing support and overstepping as a leader 20:10 Listening strategies in leadership 22:27 One-on-one leadership and employee growth 24:14 Debate and innovation in Israeli culture 25:56 The future of flat, empowered organizations 28:47 Using data to improve employee experience 33:01 AI in IT support and automation 36:10 Preparing for the future of work with AI ABOUT THE GUESTS Jed Ayres is CEO of ControlUp. Gadi Feldman is Chief Product Officer of ControlUp. WATCH AND LISTEN Podcast page: https://leaderbook.ai/podcast Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/1wTqXXn... YouTube channel:    / @leaderbookai   LEARN MORE Explore LeaderbookAI: https://leaderbook.ai/ Talk with us: https://leaderbook.ai/contact Subscribe to the LeaderbookAI Brief: https://leaderbookai.substack.com/ Subscribe to the LeaderbookAI Podcast for candid conversations about leadership, AI, and the decisions shaping how work gets done. #Leadership #FutureOfWork #AIatWork