Ep 61: The AI Skill Most Directors Still Don't Have (with Courtney Kingsbury)

Polly Allen: I think it's so important to call out to other leaders that there's a lot of leadership who thinks it's about delegating or getting other people to build it for you. But now that it's so easy to

Courtney Kingsbury: get hands on the portfolio that we set up in class, it is putting out there that I vibe coach because you had a really good point that you had said directors or anybody above that have the ability to prototype for themselves is a very rare thing. And that is absolutely true.

Polly Allen: There's something it's giving you dopamine all the time. I explain it as like if you just approach it like a video game from day one, everything will be easier for you. Welcome to another episode of AI Product Leader. Every week we shine a light on what it really takes to join the AI world. Real conversations with AI builders, founders, product leaders, AI ah, experts, technologists, and everything in between to understand where the world of AI is right now and what that path looks like, whether you're building AI products or a career in AI. I'm your host, Polly Allen, the founder of AI Career Boost, where I spend my time helping product leaders and navigate the world of AI, thrive in AI roles and transition into AI leadership. And I spent my career on, um, both the product management and software development sides of the fence. I'm an ex Alexa AI principal product manager where I launched the very first generative AI answers on Alexa. And I'm especially excited to have our guest joining us today, Courtney Kingsbury. Courtney, welcome.

Courtney Kingsbury: Thank you. I'm glad to be here.

Polly Allen: So Courtney didn't just pivot into AI. She built her way in. So during a deliberate career break in 2025, she shipped her production AI systems and AI, uh, rag based document intelligence tool. Now live with enterprise clients and a conversational AI that automated a City of Phoenix neighborhood grant program delivering over 120k in savings to 600 homes with zero added city staff. That builder's track record landed her role as director of AI strategy and data governance at a renewable resource asset management company where she's now constructing the AI and data infrastructure powering global renewable energy asset management across solar, wind and storage. She brings 15 years of enterprise depth from managing over $500 million in portfolios at American Express to driving global product strategy across 38 languages at TTI Success Insights and has a rare gift for getting executives, engineers and operators aligned on what actually matters. She also co hosts importantly the Career Blind Spot podcast with her husband, Courtney. Welcome so much for being with us today.

Courtney Kingsbury: Thank you. I'm so happy to be here. This is great. I love that introduction. I didn't know how impressive I sounded until this.

Polly Allen: It's been really amazing to see your rise in AI and the intentionality you put into that. So before we get into your current AI exploits, so I'd love to hear a little bit more about your background before you were interested in AI. Like, what were you doing in your earlier career and, um, what made you decide to pivot into AI?

Courtney Kingsbury: Yeah, so I started my career off at American Express just as a call center representative and found out how much I loved working with numbers. So I moved into analytics, fell a little bit in love with Excel, and just kept doing the financial analyst thing. Decided I was a little bit burned out, and went on to try something new. And so I ended up at my last company working on localizations and all those different languages to update all of our products, um, into those languages. So it was really cool. And then I took the step back and changed my life.

Polly Allen: Yeah. So I'm sure a lot of people kind of daydream about, like, taking time off to reskill. Tell us a little bit more about, like, went into that decision.

Courtney Kingsbury: I had been in your class, I think, for two weeks, and I wasn't able to devote as much time to it as I wanted to be. And so I went to my husband, and I was like, I'm gonna quit my job today. He goes, okay, cool.

Polly Allen: That's.

Courtney Kingsbury: He was like. He was all in. Yeah, he was all in. All in on the. On the everything. Yeah, he was very supportive.

Polly Allen: You were like, I just. I really need to go all in. And what was it about, um, AI specifically, that you were like, I just need to go all in on this?

Courtney Kingsbury: I feel like it's the natural progression for somebody who likes data and numbers and figuring out how to build things right from the first. Like. Like, there's just so much opportunity there for people who think that way.

Polly Allen: Absolutely. So before the class, you joined the AI Caribbean blueprint. Had you built things before? Have you. Have you built. Built software before?

Courtney Kingsbury: Software? No. I was acting as a junior developer, kind of for some of my engineers at the last company. And then I had built an AI product having to do with translations. And I remember explaining this to you the first time that we met, and you saying, that's a human in the loop system. And I was like, what? What is that? And so I was so excited to know, like, I had been using AI without even knowing what I was doing. And it was really cool.

Polly Allen: Yeah, absolutely. Exactly. Just because it isn't interactive with your customers. Doesn't mean it's not a AI. Absolutely, absolutely. Um, so you built multiple things during the, during the program. Before we skip forward to what you're doing today, um, in your new job, can you go over a little bit about some of the systems that you built? Building an enterprise rag system is no mean feat.

Courtney Kingsbury: Yeah, uh, I built that for my capstone. It was very interesting. It was an idea that I had while I was still working at my last employer because every company around me was saying, we want to be in AI. And I felt like having just their knowledge in a searchable format with citations would be the easiest way for people to say we have AI. So that's what I was working on then. I love that. And then I was doing the city of Phoenix. Um, I had run a tree grant outside, uh, of AI just for my entire neighborhood to have access to two free trees. And it was a lot of work. And the person who was handling it within the city left the job. And so I decided I can't do all of this and do AI. So I set up a whole website with a chatbot. It had little quizzes in it to tell you what kind of trees you want. I had a shade predictor that would show you where to do the placement that's ideal and then a history of how, you know, shade was built into our original neighborhood. So it was really fun to build and I feel like I learned a lot. It was my first time playing with, like, chatbot, uh, architecture and yeah, it was really cool.

Polly Allen: Do you have, um, some favorite tools to build with when you're, when you're

Courtney Kingsbury: building, it's just all the time. Yeah, yeah, I, I'm in love. I'm obsessed. It can do anything.

Polly Allen: Where did you first meet Claude? Was it, was it in our classes or did you find it?

Courtney Kingsbury: Yeah, yeah, I was using ChatGPT up till that point. And then you said how much you love Claude. And I was like, I guess I'll try it out. And I did. And I was like, I'm never going back. I closed down my ChatGPT account.

Polly Allen: Amazing. Amazing. What do you, what do you think of it is about it? I'd love to jam on this because I'm cloud pilled as well.

Courtney Kingsbury: Oh my gosh. I love the way that it responds to everything. I love that if you tell it to be critical, it actually remembers to be critical of everything. I love that you can give it the projects. Oh my gosh. The projects are where I'm Obsessed right now. It's where all of my documentation lives. It can be my second brain to have a different set of eyes on things. I think Claude code. Oh my God. Opening up that terminal and feeling like I'm tech, tech savvy and having a conversation like build and prototype things is just so incredibly addictive.

Polly Allen: Totally. There's something very, um. It's giving you dopamine all the time. I explain it as like, if you just approach it like a video game from day one, everything will be easier for you.

Courtney Kingsbury: Yes, yes. I think the favorite thing, my favorite thing that I've built in cloud code recently is, um, briefs for the company. So they're interactive, better than PowerPoint. They can actually go in and see how things flow through a diagram. And cloud code's just amazing at building all of that. So, yeah, it's great.

Polly Allen: Tell me more. An interactive brief. So it's like dynamic HTML or something where they.

Courtney Kingsbury: Yes, it's HTML and it just is going through all the different parts of what it is that I'm proposing. But like in my most recent version, I have what the internal customer would see, so they know that we don't have to retrain them. And then on the back end, where everything goes, you know, if it's a security question, it goes over here and it just kind of routes everything. And it is so helpful to have that visual for some people.

Polly Allen: Absolutely, absolutely. So when you're trying to do something organizationally like this, um, yes, you can see it's a big advantage. Well, let's, and let's talk about that, your role in this new organization. So what are the kinds of challenges you're, you're taking on at this new company?

Courtney Kingsbury: So this new company is fantastic. I love them. They are very new to AI products right now. They are, they have a lot of challenges. You know, data is always a challenge, especially for a legacy company, and cleaning it up is a big challenge. So we're looking into some things about semantic searching so that we don't have to back clean the data. Um, we have a lot of opportunity, I think, to use the historical data from this company to do some really cool things like digital twins and some different options that are out there that are just really incredible.

Polly Allen: Yeah. Is it because they've done good tracking of existing data that they have more opportunity with this?

Courtney Kingsbury: Yes. So 13 years of back data. Yes. But most of it is in PDF form, so. And different like contracts and things. So finding a way to pull out the information somewhat, standardize it, you know, create that Semantic library and then be able to push it through from bronze to silver to gold. That's where we're at right now.

Polly Allen: Oh, amazing. But taking on a big strategic project like that, um, it must. It's. It's interesting.

Courtney Kingsbury: Do you.

Polly Allen: You obviously love to build and get hands on. Uh, but then how do you think that relates to this role where you're like, oh, I actually have to, like, think big about what the whole company is going and actually get, like, adoption amongst the whole company. Are they very different challenges? Does the building help?

Courtney Kingsbury: The building was part of the job description, so that was what made me interested in this company. So it came down to a few companies at the end with offers that I had, and this company was like, we want you to build things. And I was like, sold. Let's do this. Let's go. They wanted somebody in the posting that said specifically that can vibe code. And I was like, I'm your person. Let's go. Oh, that's, um, awesome. Yeah. So they're super cool. They are very impressed with the things that I can build for them. They love, like, the brief, so I'm very happy to be there.

Polly Allen: That's awesome. Excellent. I think it's so important to call out to other leaders that there's a lot of leadership who thinks it's about delegating or getting other people to build it for you. But now that it's so easy to get hands on.

Courtney Kingsbury: Yes. Yeah. I like the opportunity to learn how to be a director. So I just kind of set up the architecture, but let somebody else actually build it. So that's. That's so exciting for me.

Polly Allen: Yeah, absolutely. Absolutely.

Courtney Kingsbury: Yeah.

Polly Allen: Um, because this is officially your first role as director, correct?

Courtney Kingsbury: Yes, it is.

Polly Allen: It sounds like you've had other roles where you were. You were doing the work, but this is the one where. Yes, it's official. On. On.

Courtney Kingsbury: Yes.

Polly Allen: Line item.

Courtney Kingsbury: Yes. I have my long title. Yes. I love it.

Polly Allen: And remind me of the timeline. When. When did you come through our program? I'm forgetting now.

Courtney Kingsbury: Let's see. I finished in November, so it would have been September.

Polly Allen: Yeah, gotcha. So October, September, November. Awesome. And then by the spring, um, you're comparing offers from multiple companies. That's absolutely.

Courtney Kingsbury: Yeah. Within six months. Yes, absolutely.

Polly Allen: Incredible. What do you think accounts for, you know, the, The. The popularity or being able to get that kind of attention?

Courtney Kingsbury: It is, uh, the portfolio that we set up in class. It is putting out there that I Vibe coach, because you had a really good point at some point that you had Said directors or anybody above that have the ability to prototype for themselves is a very rare thing. And that is absolutely true. I feel like all directors and VPs need to learn those skills because it's not done right now. And just being able to do that for yourself, to show a visual to somebody above you of how things are going to work, is going to be so much easier to explain and get the buy in.

Polly Allen: Absolutely. Absolutely. I'm so glad you're finding that, because I think, um, the people have been succeeding are just like, I've taken these tools. Um, did it take you, if you could build two, four months to learn it? How quickly did you pick up vibe coding?

Courtney Kingsbury: I think I picked it up pretty quickly. So I had been doing that junior dev role, uh, at the last company, so I knew how to use VS code and terminal and all those fun things, so it wasn't a huge leap for me. But, you know, there's a difference in between being able to do something fun and then being like, I should probably figure out how to read all of this before I hit submit. Yeah, there's definitely a difference there. And I think over time, I got more comfortable with it for sure.

Polly Allen: Totally awesome. Well, it's so great to hear about your trajectory on this space. You're also building some personal projects. We'd love to hear more about that.

Courtney Kingsbury: Yes. So my current personal project is really exciting. So it is. I call it the Command Center. The Kingsbury Command Center.

Polly Allen: Nice.

Courtney Kingsbury: So it does a lot of different things that I just wanted in one place. Um, so it does like your routine and your chore tracker. My husband and I have a little bit of adhd, so having this reminder is really helpful. But to keep it from getting boring, it changes backgrounds every day. Uh, it changes what screen you're on for the person who's using it, which device you're on. I just put in, uh, the option to do recipes where you actually speak to Claude, and it gives you some ideas for recipes, and it updates your grocery list for you, and it's just really fun. Um, and right now I'm trying to get it set up so that it will give me feedback about, like, hey, these chores were done this week. These ones weren't. Hey, you and Juan talked about money this week. And, and that's great. Let's. Let's figure out what we're gonna do next week to, to 10x your productivity and make things better. So it's really gonna be something when I'm done with it, which I'm very

Polly Allen: close so it's not just a work hack, it's a life hack.

Courtney Kingsbury: Yes, it really is. Yeah.

Polly Allen: Incredible. Any plans to open source this? I feel like I need this. Yeah.

Courtney Kingsbury: I mean, who knows? Yeah, that could be a thing.

Polly Allen: Wonderful. We'll talk. We'll talk, at least. Been diagnosed with ADHD BY A, uh. TikTok certainly thinks I had ADHD. So, yes, at this point. Awesome. Amazing. Well, Courtney, it's quite the transformation, right, that you've gone through. And obviously it was done with, like, this intentionality to go all in. But can you tell us what made it possible? What helped you get there?

Courtney Kingsbury: The support of my husband. I'll say. The reason that I. I was all in on this was I went to your webinar on LinkedIn and the information that you gave out in the webinar alone, I was like, oh, my gosh, I have to take this class. This is exactly what I want to do. This is somebody who wants to help people who aren't in tech get into this. And I went and I told my husband, I want to do this. And he was like, great, okay, let's do it. And so, you know, just taking the step back when I needed the time to actually go full in, because you. You have everything at different levels, and I wanted to go every level. And I actually found out how much I love to build stuff because I had been called, you know, techish or scrappy or a tinkerer in the past by other people. And I was like, now I have the power to vibe code.

Polly Allen: Yeah, that's incredible. And it's the most rewarding thing to see people like you empowered and just running. Running free. That's amazing.

Courtney Kingsbury: Yes, yes. Empowered is the right word. And people who normally wouldn't be in this space now have the option to be here. I think it's fantastic.

Polly Allen: That's incredible. If you had advice for anyone who is just starting out, who's like, I know I want to build, but how do I start? What advice would you give them?

Courtney Kingsbury: I mean, just. Just try, try, try. Cloud code, first of all. I mean, uh, they have it in the. The window version. Work on that until you're comfortable, then do it in terminal. Figure out how to read what it's writing so that you can approve it. Like, just start somewhere. You really can't mess it up. Just go try it.

Polly Allen: Fantastic. I love that advice because I feel like so many people are like, I went into Claude, but I didn't know what to say. And you're like, literally just brain dump what you Want to build?

Courtney Kingsbury: Yeah, yeah, yeah. Turn on dictation and just dump everything. Yeah, yeah.

Polly Allen: It'll help you. It'll walk you through it. It's great. Fantastic. That's amazing. Courtney. Thanks so much for, uh, imparting your advice here too. Um, so we have section one. Uh, one last section. Time for one last section. And that is plugs. And I'm happy to know I'm not the only one with the podcast here.

Courtney Kingsbury: Yes. My husband and I co host a podcast called the Career Blind Spot Podcast. And so I really recommend that people listen to it. It's a lot of fun. We've been doing more video where you can see the two of us kind of go back and forth, and it's kind of fun.

Polly Allen: Career Blind spot. So is it about career blind Spots? How. How does it. Who should tune in? Yeah.

Courtney Kingsbury: So Career Blind Spot's the name of my husband's company. He's an executive consultant for career specific changes.

Polly Allen: Amazing.

Courtney Kingsbury: Um, so if you are looking to change your career or you're looking to figure out what it is you want to do with the rest of your life, that's what he does. And that's kind of what we talk about on the podcast is how. How to apply it in different situations.

Polly Allen: Oh, amazing. Maybe we should do a joint episode, to be honest. Awesome.

Courtney Kingsbury: Oh, I love that.

Polly Allen: Fantastic. By side, I always like to plug, um, our newsletter and our upcoming master class. So we do have upcoming master classes, um, @aicareerboost.com master, um, AI leadership. So do come join us for our next masterclass, um, where we're always trying to elucidate exactly where the, the, uh, the career trajectories of leaders are going right now as it relates to AI, and you'll learn some of the key skills you need to in order to succeed, um, and rapidly ascend like Courtney has. Thanks again so much, Courtney, for joining us today. I really appreciate it. It's been wonderful having.

Courtney Kingsbury: Thank you for having me. Yeah, thanks for having me. This was super fun.

Polly Allen: Awesome. And that's our, uh, AI Group podcast for this week. Thanks so much, everyone. We'll talk to you soon. Bye for now.