Ep26 Matt Oess -Coaching Elite Leaders, AI Productivity & The Need for Tech Diplomacy
Episode Summary
Matt Oess, a sales and marketing consultant and executive coach at TechCXO, discusses his work coaching C-suite leaders, his deep dive into AI productivity tools, and his involvement with Purdue's Croc Institute for Tech Diplomacy. He demonstrates practical AI automation workflows, explores how AI is transforming business operations, and shares insights on protecting critical technologies from adversaries through diplomatic policy work.
Key Quotes
"Coaching is for people who want coaching. It's the one place on the planet where there's no judgment, complete confidentiality, and you can be vulnerable—because being a founder or CEO is a lonely place where you have to feign control while not actually knowing everything."
"The value of AI isn't in the LLMs themselves—it's all in the software side, the multi-agent systems and custom agents. We're just barely starting to scratch the surface of what this stuff can create."
"I just wonder if SaaS changes. Does Salesforce become the data repository while smaller companies create the sales agents and marketing agents because they can innovate faster? Can they still charge $1,500 a year or do they get relegated to being the database?"
Transcript
Hi, welcome to Tales From The Sky Lounge, it's a podcast about business consulting and venture investing. We get out there in the world, we talk to people who are making it happen, and we get their stories. Today's guest in the Sky Lounge is Matt Ow. Hey Matt, how are you?
Hey Todd, longtime listener, first-time caller. Thanks for having me here.
I remember that guy. I always wanted to say that. Well, hey, who are you and what are you working on?
So I work for TechCXO. I've been here just over 12 years. My practice is mainly sales and marketing consulting—maybe half of my time is spent there. The other half of my time I spend leading our executive coaching practice. For the last 14 or so months, life has just been an incredibly deep AI dive.
Very cool, and I'm sure we'll get into that. AI is on the lips of many people out there in the world and it's a complex subject for sure. So let's talk about your coaching practice. What stage of company do you typically get involved with in your day-to-day coaching?
Want to go deeper?
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