Executive Mode: Inside the AI Playbook of Serial Entrepreneur - Rob Bailey

​Welcome to Episode 2 of Executive Mode - the series where we sit down with executives and founders across industries to talk about how they are actually using the latest technology in their day to day, and then have them show us live.

​This episode we are joined by Rob Bailey, a founder & operator who has built and scaled some of the most recognized companies in tech. We get into how he is personally leveraging AI across his workflows, the tools he swears by, and the ways it has changed how he operates at the highest level; then he shows us exactly how he does it.

​If you want to see how the best in the business are really using AI, this is the episode for you.

​Our hosts🎤

​Gus Spathis
Founder & CEO, Xogito

​Gus’ career spans over 30 years, managing businesses and award-winning teams and technology. He has focused on realizing entrepreneur’s visions by solving difficult problems efficiently and creating breakthrough solutions.

​As an entrepreneur himself he has participated in founding over a dozen different companies. He is a sought-after advisor by venture capitalists, angel investors, and private equity firms.​

​​Rob Bailey
Serial Entrepreneur

​Founder and operator focused on building category-defining AI and enterprise software companies. He has been part of the core teams behind multiple category winners, including DataSift, Kustomer, and CrewAI. His work centers on the new playbook for AI-native companies—where product, positioning, and go-to-market are tightly integrated to drive rapid scale.

​​About Xogito

​Xogito partners with startups and enterprises to design and deliver scalable, high-performance systems using modern engineering and AI-driven practices. With over 20 years of experience, Xogito helps teams launch new products, rebuild fragile MVPs, modernize infrastructure, and implement intelligent workflows that scale with the business.