Episode Summary

Matt Oess, a sales and marketing consultant and executive coach at TechCXO, discusses his coaching practice for C-suite leaders, his deep dive into AI productivity tools over the past 14 months, and his advisory role with Purdue's Croc Institute for Tech Diplomacy. He demonstrates practical AI automation workflows he's built using platforms like Make.com, explains the maturity progression from zero-shot generative AI to multi-agent systems, and shares insights on how AI is transforming business operations and the SaaS industry.

Pull Quotes

“Being a founder, being a CEO, being a C-suite executive—it's a lonely place. You have to be transparent to your board, but you can't be fully open because if you were fully open, they'd probably throw you out on your ear because they'd realize you don't actually know what the heck you're doing. That's not just them, that's humans.”

“I'm not your therapist, I'm not your counselor. Those people are doctors and professionally trained, and they help you with some wound in the past so you can be healthy and productive in the present. A coach is somebody who takes somebody that's perfectly healthy in the present and accelerates their journey to a better future that they want.”

“I think the LLMs are really important in this fight for supremacy or to be better faster or cheaper or however they're going to build these things. I think all that's important for the underlying foundation of the innovation and obviously the chips are important in order to make that stuff real but I don't even think we've started to scratch the surface on the value that this stuff is going to create because the value is all in the software side of this thing and these multi-agent types of things and custom agents.”

“I literally haven't written code for 30 years. Back in the day I worked in this Advanced Development Lab for General Motors and we incubated in the early '90s some of the stuff that's in cars today. Then I said I turned in my engineering card and 30 years later I'm writing code again and it's only because of AI that I could possibly do this.”

On the future of SaaS platforms like Salesforce

“If you're Salesforce and you're trying to figure out how to create an agent for a salesperson to be more productive, are you going to be able to take every single one of your clients and train the AI model to fully understand their solution set, their context, all of their emails, like everything that you're going to need in order to let AI do the intelligent things that you want it to do? I don't know if they're going to be able to do that and I don't know if they're motivated to do that because if they do that, can they still charge $1,500 a year or $700 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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