Ready.Set.Midmarket! Podcast: Leading The Girl Scouts’ Technology
In this episode: The Girl Scouts have great cookies, but did you know they also have great technology?
Join us in our discussion with Michael Pompey, the Chief Information and Transformation Officer of the Girl Scouts of Eastern Pennsylvania. Hosts Adam Dennison and Samara Lynn speak with Pompey on AI's impact on corporate culture, the significance of "soft skills" for IT executives as well as the importance of a human connection in tech, policymaking, and more.
The full episode can be watched on YouTube, heard on Spotify and Apple Podcasts.
[Previous RSM! Episode: The Midmarket's Tech Road Ahead In 2025]
TRANSCRIPT:
Adam Dennison (00:05)
Hello, welcome to Ready, Set, Mid-Market, the podcast for the latest news, expert insights, tips, and trends for mid-market IT leaders. I'm Adam Denison, Vice President, Mid-Size Enterprise Services with the channel company. Joining me today is my co-host, Samara Lynn. She's the senior editor at mescomputing.com. So today's episode, look, you can't go anywhere right now, let alone technology, without talking about AI.
We're hearing it in all aspects of business, all aspects of our life. But today we're going to take a little different approach and kind of go beyond the technology and talk about how it affects corporate culture. And joining us today is our guest, Michael Pompey. He's the Chief Information and Transformation Officer with Girl Scouts of Eastern Pennsylvania. Michael,
Michael Pompey (00:50)
Thank you, thank you for the invite. I love this topic, I love the group that we're working with and so this is so right on point.
Adam Dennison (00:57)
Awesome, thank you. So Michael, before we get started, can you just tell us a little bit about yourself, your role, Girl Scouts of Eastern Pennsylvania, what it is that you do, the size, the scope of your organization?
Michael Pompey (01:08)
sure. Sure. So, uh, you know, as I'm sure most folks listening to this, you know, are probably familiar with the Girl Scouts, uh, familiar with probably, you know, our, one of our flagship programmatic experiences, the Girl Scout Cookie Campaign. So I, you know, would be remiss if not saying that we are in season. So if you see Scouts and troops out there selling, please stop by and purchase. This is the world's largest, uh, programmatic girl run enterprise. We're talking $2 billion, um, worth of goods that girls get a chance to learn entrepreneurship, be able to reach customers, marketing and all these things. So it's a great program. So with that out of the way, being the chief information and transformation officer here at the Girl Scouts of Eastern PA, I've got the honor and privilege of lending my services to an organization that's really pushing girl centered programming as well as development for leadership in our community today.
In my role as chief information and transformation officer, I really lead the organization and how we not only leverage our technology, but our data as it relates to not only how we service the girls and families from our diverse communities and the nine counties that make up Southeast PA's footprint, but also how we leverage this to make sure we take the messaging on the products and the services related to Girl Scouts to all those in our footprint that could benefit from it. So those are my roles here at our organization. Girl Scouts as a whole, Girl Scouts of America has 110 different councils underneath it. So we don't necessarily compete with each other. We are spread out geographically and Eastern PA is the fifth council in size nationwide. So we are a true enterprise. So why folks tend to think of Girl Scouts as camps, cookies and crafts, we are way beyond that. A story I often share is when I first joined council, cause as you can probably guess, I was never a Girl Scout. But when I first joined council, what I realized is that my Cub Scout experience was not as good as a Girl Scout experiences that girls have today. And I was like, wow, I was really on the other side of the coin. This place has really got their stuff together. STEM, robotics, some of the really cool things, some of the girl projects are doing. I was like, we never really had any of this in least my limited Cub Scout experience. that's Girl Scouts at Eastern PA. That's kind of, my big levers that I try to pull as it relates to the organization and the work we do in our area.
Adam Dennison (03:21)
Outstanding. Well, I can I can certainly tell you I've been a consumer for a long time of the cookies and I also have two daughters. They're now 18 and 13, so they're they're they're no longer Girl Scouts, but my wife was the one that had to coordinate it all. So we had boxes and boxes of it in our basement and trying to get it out and distributed and all that.
Michael Pompey (03:26)
Thank you for that.
Mmm.
Excellent. Yes.
Yes. Yes. You know, well, like we always say, once a Girl Scout, always a Girl Scout. So there's still room for the 13 year old. But yes, you'd be surprised just, you know, how many leaders in the industry, whether it be, you know, astronauts or senators or, you know, entrepreneurs, CEOs, executives were previously Girl Scouts. Those lessons go with you as you leave the organization. So I'm so glad to hear that.
Adam Dennison (04:00)
Excellent. Samara, do you have any Girl Scout background?
SAMARA LYNN (04:03)
just a big consumer of the cookies.
Michael Pompey (04:06)
Well, we thank you for that. We thank you for that. Keep buying them. Keep buying them.
Adam Dennison (04:09)
So Michael, let's move now into AI a little bit. And before we get into the kind of the culture piece and how you want to address that, can you talk to us about, you know, when did you start implementing AI in your organization? What came first? How did you decide what came first? How is it being used? And I know a lot of folks just kind of like cloud will say AI has been going on for years, but
Adam Dennison (04:32)
Let's talk about the modern AI and what you're doing within your organization there.
Michael Pompey (04:37)
Right, right. So you are correct in that, you know, a lot of the tenants for AI have been around for years. And some of the things that, you know, I've played with that previous organizations as well as here before coming here, really related to a lot of the automation pieces that folks tend to look at as it relates to what these technologies can do. So specifically here, you know, as we take a look at, you know, where are the places that it does hold potential for the best work, it is places not related only to data and informatics and building up sort of machine learning models related to our data, related to be able to track, you know, where are the best places you have the ability to actually attract and keep girls as far as programming, but also taking a look at, you know, as it relates to the customer and getting information to them in an easier way. I always say that the bar for us and our world, whether you're nonprofit, for-profit education or workforce is not being set by other organizations in your same industry. It's being set by your Amazon, being set by your Twitter, it's being set by other places where folks have easy access to their data and they engage with those systems first before being pushed over to the limited bandwidth as it relates to one-on-one human interaction. So for us, we've taken a look at developing some test models and LLMs that could actually sort of help a parent or a family find areas as it relates to, hey, my girl is interested, where can I go? Hey, I'm interested in doing these things and training that based on our data to say, hey, here's a place you can actually go, here's what their availability is, here's what appears to be closest to you, and start that process versus what for many may seem to be cumbersome, waiting till you get an email response back, getting somebody on the phone, taking a look at, okay, let me look up where your zip code is, hey, do you think this school might work, do you think this school might work? So being able to feed that into a model that actually knows that information and be able to present it in a format that's conversational.
It's already an LLM, so it already has your language models baked into it, as well as collect the pieces of information that are to be necessary for the member services team to actually get you signed up are areas that we're looking to explore and that actually created an initial pilot.
Adam Dennison (06:39)
Interesting. So when I think about culture of AI and what it does to a culture, a lot of where I go is potential resistance. There's a lot of the scare of it's going to take my job and things like that. What is your experience as far as from a culture standpoint and how your large mid-market organization is accepting it and how they're utilizing it and things of that nature?
Michael Pompey (07:02)
Well, it's interesting, you I often tell other technology leaders, know, if you think you have the ability to put a wall in front of this technology and keep it out in your environment, you're already diluted. Your people are going to bring this into whether you tell them they can or not. The idea that a piece of technology on its own eliminates a job is not really faulty. It's usually a person or a company leveraging that technology that will eliminate the job. So the quicker you are to embrace what it can actually mean for your organization, the better you will be unable to push back against some of the challenges that you're going to be finding in the market. I think for a lot of individuals, some of the first things they worry about is, okay, is the ability to hold onto information and be analytical going to be the insurance for me keeping my job in a particular role. Well, we see the power of some of these models as it relates to doing that, that that by itself may no longer be the insurance, the safety blanket that folks tended to think about. However, there are other pieces that these models probably will never ever be able to do that become more important in an organization that wants to be forward thinking and leading their space. And I think that's the piece that leaders need to be able to embrace that conversation internally to make sure that they keep the best of the best as well as move forward.
Adam Dennison (08:20)
Yep. Go ahead, Samara.
SAMARA LYNN (08:23)
Yeah, I remember it's almost the same thing with cloud computing and SaaS apps, right? People were like, it's a cloud. You don't need network administrators anymore but you still need people to integrate and manage those services. So I mean, to me, it's almost the same conversation years ago with the advent of cloud computing.
Michael Pompey (08:38)
Right.
Yeah, right, right. If you think about, you know, during our careers, there have always been these sort of, you know, watershed moments where this piece of technology has come out and it was going to change the landscape, right? And, you know, and whether it was cloud compute or low code, no code or edge devices or all these different things, they all set the same thing. Now, yes, they changed the landscape. Yes, they changed how we did our work, but it did not eliminate vast majorities of individuals. It definitely shifted where effort took place, right? And I think the same thing is happening here and listen, and I, you know, I also know at the end of the day, look, AI and bots and all this other kind of things, they're not going to buy all the stuff that people generate. So they're still going to need a human with the ability to buy the goods that they manufacture. It's not in anybody's interest to put everybody out of work because then no one's buying their stuff. Right. So at the end of the day, you know, there is a wheel and now the stuff moves around and just knowing where you are that will and understanding that can alleviate some of the hype and drama that's inevitably shows up.
Adam Dennison (09:38)
What does that look like in your organization at the C-suite level? You know, the other business heads, are they constantly asking about AI? Because again, it's on Super Bowl commercials, it's everywhere. Are they asking about it? What are we doing? And they might not exactly know everything that you are already doing and it's kind of an education process there.
Michael Pompey (09:59)
Well, you find the education process not only with the fellow members of the C-suite regarding what currently do you have internally as it relates to AI resources, but what their individual teams are leveraging and utilizing. Because a lot of times you may have a savvy employee or a staff member pulling in tools or doing things at home with data from the company to enhance their own productivity without anyone else knowing about it. So how do you stand up the sort of internal, hey, let's set up our own little [...] work where we sort of share information, what tools are you using? What do you find actually helpful? How do you actually do this to speed the table? But you also have it from your board because many of these members sit on other organizations that are larger to have the same questions, right? Well, what are you doing with AI? What are you doing with machine learning? Where does this take place? What are the risks associated with people taking data that's proprietary and sending it to a model to turn something around really quick, but not necessarily noticing that, hey, you know what?
Not only are you giving your data away and training somebody else's model, but that's no longer yours. Right. And what happens if that gets out? so those questions we constantly, are having in our organization. Like I said before, even though we're Girl Scouts, we are an enterprise. we have, you know, an IT strategy council of our board. have, you know, full board conversation. We've got these things at their executive team meetings, where we have these conversations about what this takes place because whether or not we embrace it, guess what? Our girls are getting exposed to it and it's becoming easier to get access via the mobile devices de jure that lot of kids have access to. So making sure that we're on the cusp of that with them is so important this day and age.
Adam Dennison (11:28)
Yeah. You mentioned policy and that was about a year ago when I would be out doing round tables and talking with mid-market IT leaders. If there were 10 of them in the room, maybe one had a policy in place and the rest were like, can I see it? Can you scrub your data out of it? Can I see what you have so that I can, I've got something in place as well. I think obviously that's maturing some now.
SAMARA LYNN (11:37)
Hmm.
Michael Pompey (11:45)
Yes, let me copy your homework paper.
Adam Dennison (11:52)
Where are you at in terms of setting up a policy and having people sign off on it and following that policy and checking and reviewing it and updating it and things of that nature?
Michael Pompey (12:02)
Right, so what are the benefits of working in sort of this federated nonprofit is that you do have a mother organization across the top. And so, you some of the things that we get to share as far as being a member of that top 10 is we do share some of the guidelines and the governance policies with each other related to what are you doing in your environment, as well as incorporating those within our own acceptable use technology plans, which we review every year, some of our own internal processes on our own, because each council is an independent 501c3. So we're our own organization. So while I know the IT leaders from the top 10, and we share information back and forth, I don't write their policies, they don't write mine, but we do share information. So for us, it really is how do we make sure we address risk? How do we make sure we address the privacy controls as well as security? Because not only are we using AI and all these different tools, sort of bad actors trying to get into our environments, right? So making sure that our vendors are ready. We've got the appropriate technology that can help leverage this to sift through the noise, if you will, related to what's actually true signal versus what's a distraction and making sure that we kind of balance it. That's, I mean, that's the secret sauce for any CIO and trying to get that done.
SAMARA LYNN (13:10)
And it really is like not just your organization, but your partners, your vendors. It's like the whole supply chain. You have to apply the policy completely down the line. That's quite a feat.
Michael Pompey (13:18)
Correct.
Correct.
Listen, it is quite a feat and all it takes, listen, I know there have been days where it's like you read the news and whether it's CrowdStrike or the data breach at Target or something like that, and you're like, wow, I'm glad I'm not that CIO. But at end of the day, that is the web that we have to try to do our best to mitigate these risks. does anyone get it 100 %? Of course not. Do you try to do your best and make sure you're forward thinking? That's the crux of the role. Listen, it takes a special kind of person to wanna stand in that spot.
SAMARA LYNN (13:37)
Yeah.
Michael Pompey (13:54)
Thankfully, the world has us, so thank you for your service, fellow CIOs. But at end of the day, that's our job. That's what we sign up to do.
SAMARA LYNN (13:58)
You
Adam Dennison (13:58)
Yep.
SAMARA LYNN (14:02)
Right.
Adam Dennison (14:03)
So when I think about that from a future standpoint, just last week I had an advisory board one-on-one call with one of our members and she's thinking about the IT department of the future. And one of the areas that she's looking to hire right now, and I don't even know where you really begin, is an AI leader. And she's like, we need to get this in place so that we've got somebody, maybe not at the C-suite level, but we have somebody that's got some stature in the organization and they're calling the shots and taking us forward from an AI standpoint. What are your thoughts, both of your thoughts around, I haven't met anybody yet in a mid-market organization that has a dedicated AI leader. How soon do you think that's coming? Where do you think they'll come from? What kind of a background do they need? What are your thoughts on that?
Michael Pompey (14:50)
So in theory, you already have one, right? That was your CIO and your CTO, right? Their role is to make sure that any emerging technology that can affect the business and help you or hinder you in reaching your goals is understood and brought to the table of people. calling that particular position out in something else, you should already have that within your organization. I would also say it's not just one leader, right? Just like a well-run organization, it's not only one person understands finance or one... person understands compliance and risk. is the culture. It is baked into to whatever you do. so while you may assign this out to a particular person to, you know, maybe lead a conversation or maybe to be that sort of 11th person in a room to always ask that question, it's probably is not going to work out that one person is going to be your go-to. It's, fracturing too much. I mean, we've seen what happened in the past couple of weeks, you know, deep seek comes out of left field. How many.
C-suite executives with that role would have been the person to say, watch out for this, this, you know, this Chinese model that's coming out, right? It caught everybody by surprise. The other challenge is that we're all learning this together. So to be that one expert, I wouldn't want to be that guy just because everyone's looking for you to be that. Yeah. Thank you. Right. Exactly. So.
Adam Dennison (16:03)
[I]mean, Deepseek disrupted the whole stock market.
Michael Pompey (16:10)
We're all, it's all coming so fast and to be the one person responsible for knowing all of it. We already know in technology that doesn't work. We already know that your users are going to bring things into your environment, no matter what you tell them to do. So you have to be ready to, to evaluate and balance. know that the market's going to change. never know what, you know, whether it's a geopolitical situation that's going to change the landscape or some kind of natural disaster. I think having a single leader to do that, it would probably be challenging to find expensive to keep and may not net the ROI that a person's thinking about.
SAMARA LYNN (16:42)
Yeah, I mean, we just covered on mescomputing.com a report from a hybrid multi-cloud solution provider, Nutanix. And they said almost 50 % of IT leaders are looking for AI roles right now. Like they don't have it in-house. If you're old school network admin or a developer or a they're looking, this is like a whole new,
Michael Pompey (16:59)
Mm hmm. Right.
SAMARA LYNN (17:10)
Like job role.
Michael Pompey (17:10)
Well, it is. And I would challenge those places that would think that you could buy a single leader for AI to define it. Because we already know it's five, six, seven different disciplines roped together. Right. So when you're talking about AI, are you talking about generative? We're talking about machine learning. We're talking about visual, right? Which piece are you stitching together? And then which piece within your environment, right? Is that going to play out? And then trying to find that exact person. I think that gets to the issue that we were going to be talking about today as it relates to what happens to culture.
SAMARA LYNN (17:18)
Yeah.
Michael Pompey (17:39)
And that a lot of this talent that folks are looking for, they may have to think about retaining it versus trying to go out and acquire it because it's going to be so niche that, you know, you're going to be in a bidding war with other individuals. And unless you're, you know, the top 20 or so, you might not have the pockets big enough to go out and buy that technology or to buy the expertise that fits your organization, you know, like a key to a lock. that's, think some of the other things that's showing up culture wise for folks to kind of get ahead of.
Adam Dennison (18:07)
Do you see that? We still hear it, but we certainly heard it over the past few years, a lot around security. And again, from a mid-market, mid-market, it's a big landscape. There's a lot of companies in there. And some have more resources than others. But when I talk to folks around security, they're always concerned that they elevate somebody, they put the training, everything behind them from a security standpoint, and then they get picked off and get 30 % raise. And now they're kind of back to square one.
Michael Pompey (18:20)
Hmm.
Adam Dennison (18:36)
Do you see that, you just said that folks are looking for AI roles and whatnot. Do you see that as kind of that next wave is, you you build them up, you know, all good leaders want to build from within and then someone leaves and then they become part of your CIO tree or your coaching tree if you want, I'm a big sports guy. But do you see that as sort of that next wave of, you know, we build people up in this specific discipline and then they get picked off for greener pastures?
Michael Pompey (18:52)
Ha ha ha.
Well, and here's the thing, right? Why do people leave for greener pastures? It's not always because of the numbers, right? Studies have actually shown that, right? And I think when we take a look at what AI is doing to the culture and what it's sort of redistributing as it relates to importance, you will see that the things that are becoming more important are things about strategic insight, the things about collaboration, things about communication, things about strategy and being able to integrate with other people.
Not so much a lot of the quantitative, right? A lot of the throughput, a lot of the single contribution stuff that tended to be emphasized with technology positions and things of that nature. So you want an AI person, I'm going to scale him up. I'm going to train him, but I'm afraid he's going to leave. I flipped that question when I talked to other leaders, what if he stays and you don't train him? The other person's training their person. The other person wants to get better. And again,
Adam Dennison (19:49)
Yep. Yep.
SAMARA LYNN (19:52)
Yeah.
Michael Pompey (19:56)
If it's spread and not within one individual, right? You mitigate a little bit of that stuff. But at end of the day, you want an environment where people are choosing to stay with you, not necessarily looking to be transactional. And again, that is a culture piece, right? listen, we've seen that show up over the past couple of months when we've looked at what's happened to leaders in certain situations where they've led by a transactional nature. doesn't just stay within their culture. Sometimes, not to cite any health insurance CEOs, sometimes it will show up outside your culture and be brought to you. And I think that's the other piece that sometimes business leaders may forget that your culture can sometimes extend beyond just the confines of your building.
SAMARA LYNN (20:39)
Yeah, I mean, and being a successful IT leader isn't, people can learn how to be a prompt engineer. People can learn how to be a coder, but it's really those soft skills, learning how to speak to the C-suite, learning how to align your goals with the company's business objectives. That's what makes you valuable.
Michael Pompey (20:52)
Mm-hmm.
Correct. And those things that, we would traditionally call soft skills when we think about it, it's really emotional intelligence, the piece that a lot of folks, when you talk to leaders, when they complain about, you know, the, Gen Z and the millennials and all this other of stuff, a lot of times they're complaining about some of those pieces. And I think having a culture that can embrace all the different individuals that are coming into the workplace, as well as the boomers that are leaving the workplace become more important because they're not going away.
Adam Dennison (21:25)
So we just have a couple minutes left. I have a kind of a closing type question and it's around, you know, Samara and I are in the media, you know, so we love hot topics, right? We love buzzwords and whatnot. I deal a lot with the vendors. They love them too. Our research partners at Gartner, they love them. They like to fan those. I think back in my career, know, had consumerization of IT was a big one that 15, 20 years ago. Cloud was a big one. You couldn't see a cover of a magazine that didn't have clouds on it and whatnot. Digital Transformation was another big one. You mentioned Low Code. I don't think that one got to that stature of those other ones, but yeah.
Michael Pompey (21:52)
Right, right. my goodness, yes.
Nope, nope, but it was there. It was there. A little inside baseball.
Yeah, right. That the idea that all your business users were gonna build their own applications and data and take your job. Yeah, that never showed up. That never showed up. That didn't show up. Did not show up.
SAMARA LYNN (22:08)
Yeah. Yeah. Yeah.
Adam Dennison (22:09)
But I wonder where are we with like AI exhaust, right? Are you, are you starting to hear about it too much? Yeah.
Michael Pompey (22:20)
You see it, you see it. People, and it's interesting too, right? Cause there's that whole, you know, I don't know if it's a meme or some kind of theme, right? But there's a whole thing about, you know, the internet's been dead for years and all this stuff has just been, you know, generated by bots over and over again. But folks are getting turned off by the, know, the quote unquote AI slop, right? The stuff that you can feel has just been automated. It has no human connection. In fact, folks are talking about, you know, do we want to put some kind of certification on a book that this was actually written by a person versus a genAI tool. But you've seen it, right? And you get tired of it. And again, that's the piece that I think becomes more important, that human connection, because there's something, know, a ghost in the machine, if you will, that these models do not have, they may never ever have that. That's the reason why Zoom doesn't work as well as, you know, in-face person to person, because as people, we're designed to be social. We're designed to pick up three-dimensional cues from the people that we're talking about that you do not get on a two-dimensional screen. That missing element is still playing out with these models. And yeah, you feel the AI consumption, the AI slop, and I don't want to do this. That's why there are tools that will force your browser search results to be prior to 2022. Or tools that, you know, I know for me, if I'm searching for something, I will try to go to places where I know a human made a response, whether that's Reddit or someplace else versus trying to get just this random stuff that comes back where I'm like, this is not helpful, let me see what a person has actually done to solve this issue. So I definitely feel it.
Adam Dennison (23:46)
Yep, yep, absolutely. Samara, any closing questions or thoughts on your end?
SAMARA LYNN (23:51)
Yeah, no, I mean, I agree with Michael. I mean, I get so PO'd when I have to call any place I have to go through like a chat bot or pick number one for this, pick number two when you make a call. It's very It's frustrating. Right. Right.
Michael Pompey (23:59)
Right.
zero, zero, zero, zero, give me an operator. Right. It is because you want the human that can understand the contextual cues that can hear your voice. can say,
Adam Dennison (24:04)
It doesn't work anymore.
Michael Pompey (24:13)
you know what, this is the actual issue versus being roped for efficient, know, machines are designed to be productive. People are designed to be effective and there is a difference.
SAMARA LYNN (24:18)
Yeah.
Right. Right.
There's gotta be a balance.
Adam Dennison (24:26)
Well, in closing again, Michael, thank you so much for joining us on Ready, Set, Mid-Market. Appreciate the insights. So we will see you at MES Spring
SAMARA LYNN (24:29)
Thank you.
Michael Pompey (24:30)
You're welcome.
Adam Dennison (24:35)
Have a great rest of your day, folks. Appreciate it so much.
Michael Pompey (24:38)
You got it, take care.
SAMARA LYNN (24:39)
Bye everyone.