

3 Sep 2026 · 47m · 15 chapters

Derrick Pledger, CIO/CDIO at Maximus, discusses how to deploy AI in government by prioritizing business value and mission outcomes over shiny technology, with disciplined ROI gates, AI fluency training, and “safe-to-fail” R&D environments that mimic production.
Derrick Pledger is Maximus’ chief digital and information officer, leading AI enablement transformation, cybersecurity, and technology modernization for a major government services provider. Previously he was CIO of LATOS, overseeing global IT. He is a U.S. Army combat veteran, an author, and an entrepreneur.
AI should be evaluated through ROI and process redesign (“no AI pilot” without reimagining workflows for an agentic world). Adoption is driven by training across roles (no one exempt). Innovation requires controlled failure via R&D environments and “fail parties,” balancing risk aversion in government.
Maximus trains all employees on AI; it duplicates production-like environments in India (Bangalore/Hyderabad) to test before production. He describes NDIA “hackathon as a service” to move ideas to contracts faster, and outcome-based fixed-price contracts as a reason Maximus can take delivery risk.
Written by AI. May contain mistakes.
Derrick explains the role and functions of Maximus in government services.
“For those who may be less familiar with the company, give us a little bit more context as to the company that you help lead.”
Derrick discusses his responsibilities and the dual remit of his role.
“Talk a bit about your role as Chief Digital and Information Officer.”
Discussion on how Maximus approaches AI to deliver business value and ROI.
“Can you speak a little bit more about that material impact and where you see that, not only for Maximus, but for your company's clients as well?”
Exploring how Maximus trains its staff for AI fluency and the cultural impacts.
“And that's something in these times that we just can't do.”
Derrick discusses the balance between innovation and the risks in government service.
“And I think that's in many cases, that's where we've gotten it right.”
Learn about the importance of accepting failure in innovation processes.
“software, this new REST service is going to make a workflow better.”
Explore how to effectively communicate the need for modernization to clients.
“And in multiple of your responses, you're speaking to fine-tuning that risk tolerance within the organization.”
Learn how Maximus leverages partnerships to provide innovative solutions for government contracts.
“For Maximus, we we grew up as a company where 60 percent of our contracts are just under 60.”
Discover how Derek Pledger's early entrepreneurial failures shaped his leadership style.
“And I'll tell you, Peter, it's really starting to stick.”
Explore the impact of military experience on Derek's leadership and team dynamics.
“So much of your answer, I'm sure, applies to another question I wanted to ask you, which is what your military service has brought to your leadership capabilities now.”
Hear the story of how Derek Pledger became an author alongside 50 Cent.
“up front and everything else is essentially just an input to make sure that we get to that mission or we get to that outcome.”
Derrick shares insights from his past experiences that shape his leadership.
“acting and so many different businesses.”
Derrick discusses the authors and podcasts that influence his leadership style.
“And I really appreciate you allowing me to pull it a little bit.”
Derrick talks about his morning routine and the importance of self-reflection for personal growth.
“So essentially, it allows you to get a great book.”
Peter expresses gratitude to Derrick for the engaging conversation and insights shared.
“as opposed to just being selfless in everything that I do.”

Get the gist, explore an idea or ask about something said.
On Technovation with Peter High (CIO, CTO, CDO, CXO Interviews), what are the key points of this episode?
Automatic transcript. May contain errors.
0:00It's our job to make sure that the market dynamics and what's happening from a technology perspective outside of these walls don't disrupt us.
0:11Peter High: Welcome to Technovation. I'm Peter High, president of Metastrategy. My guest today is Derrick Pledger. Derrick is the chief digital and information officer of Maximus, where he leads AI enablement transformation, cybersecurity and technology modernization for one of the largest providers of government services in the country. Prior to his current role, Derek was the Chief Information Officer of LATOS, where he oversaw global IT. He's a U.S. Army combat veteran, an author, and someone who spent his career at the intersection of large-scale technology transformation and personal performance. He's also an entrepreneur.
0:43Peter High: I look forward to learning more about each of these through this conversation. Derek, welcome to Technovation. It's great to speak with you today. Peter, thanks for having me. Looking forward to a very rich conversation. I am as well. Thank you. Today's episode is brought to you by Eleven Labs. Most enterprises trying to deploy AI agents hit the same wall. The agent itself is fine. The problem is that it sounds wrong. Robotic, flat, off-brand, and the moment a customer notices, the trust is gone. Eleven Labs develops the AI voice and audio models that give agents a human-level voice, the tone, the emotion, the rhythm of real speech, and wraps them in the full stack you need to actually deploy.
1:22Peter High: Knowledge integrations, workflow tooling, multilingual support, and enterprise-grade reliability. Build human-level conversational experiences into your products, services, and operations. Head to 11labs.io backslash technovation to get started for free. And now on to the interview. Well, let's begin, if you don't mind, with Maximus. For those who may be less familiar with the company, give us a little bit more context as to the company that you help lead. Sure. I personally have dedicated my life to putting as much technical capability into the hands of war fighters and solving some of the hardest mission problems across government.
2:03And in my current role as chief digital and information officer at Maximus, there's certainly no shortage of challenges to solve as we continue to drive the proliferation of AI. And we're really focused on experiences to veterans and citizens who depend on government for critical services. So for Maximus, at our core, we're really a strategic partner to government in the delivery of citizen services, healthcare outcomes, and mission capabilities on a global scale. But as a tech company, obviously, we're using automation, AI, analytics, and predictive insight to make sure that citizens and customers that we interact with every day to provide benefits, whether it be Medicaid, Medicare, mission systems for the Air Force or the Army.
2:48You can think of us as a systems integrator, but we're really focused on outcomes and how the interaction between systems that we manage on behalf of government. How do we make sure that the experiences and folks that are interacting with those systems are having great experiences and do not look at technology as something that's in the way? So we try to remove as much friction as we can as we deliver citizen services to one in three Americans every single year.
3:18Peter High: Wow, fascinating. Talk a bit about your role as Chief Digital and Information Officer. What's within your purview, Derek? So I have a very unique role. It's certainly not your father's, your grandfather's CIO organization. So I have a dual remit, which is all of the back office enterprise services, financial systems, etc. I do have teams that manage those, but also have a CTO function that sits within my organization also. So if you think about all things, AI or technology partnerships, things that we're partnering with Silicon Valley to bring in to make sure we are delivering new capabilities and commercial capabilities to the government.
3:59I own that, too. But I also have engineers that are delivering on contract as well. So I have about 400 engineers that are on contract every single day within the federal side as well as the states. So it's not really a P &L, but it's sort of like a blended because I'm on the hook for contractual delivery, too, even though the P &L is within the business. And I also have a team of about 500 folks in India between Bangalore as well as Hyderabad. And that team is really you can think of our India team as the hub of innovation. all things that we're doing in AI, we're really stressing the systems on trying to reimagine that the way we work, because just putting AI against legacy systems, AI is pretty much garbage in, garbage out, Peter.
4:47So I have a very unique role, and it's about making sure that we're aligning tech strategy and delivery capabilities to business outcomes. And I need to be able to stand up at the end of every year and defend that, hey, investments that we made or things that we're delivering actually had a material impact to the business in terms of margins and revenue growth, etc. So it's really a unique role. And there's no day that is boring. I will say that.
5:14Peter High: Can you speak a little bit more about that material impact and where you see that, not only for Maximus, but for your company's clients as well? This is no surprise to you. A lot of people are thinking these days about these major investments that are being made in artificial intelligence and where the value is on the other end of it. It's coming in drips and drabs in some places. Some organizations and boards are applying more pressure than others, perhaps. Where do you see, what's exciting you most about the possibilities and the material impact, as you put it? I'd say for us, like speaking on AI specifically, you know, you can't have a conversation without talking about AI.
5:50Yeah, we are. AI for us has never really been about the technology in and of itself because the technology is ephemeral. There's going to be new AI capabilities that come out next month, next year, et cetera. So what we what we focused on in partnership with our HR organization is really the human element and reimagining the way that we do work such that we can use AI as a tool and an enabler. vice just saying, hey, we're going to throw Claude at this problem, or we're going to do agentic over here on this program. So I think for us, that forced us to confront some of the legacy ways that we had done business, which were kind of a hamstring.
6:37So think about in a world where you have digital agents that are doing work. You also have humans that are doing work. Then you also have humans that are managing digital agents. The core of that obviously is data, making sure your data is curated in a way that is logical, but also that AI can make sense of the data to provide output that allows you to make decisions that will impact the business. So everything that we do from an ROI perspective, there is no AI pilot, there is no AI implementation without making sure that we, one, reimagine the process, or take a look at the process to see if it will survive in an agentic world.
7:19That is something that I force up front. And if those questions are not answered, then the answer is always no about having a new AI tool or a new widget that comes out there. During that process, because it's so disciplined, it forces us to really recognize on the other side of this implementation, how will that impact the business? Is it speed? speed? Is it cost avoidance? Is it scale? Is it making sure that we have 100 engineers that now can perform at a level that we had 300 engineers because we're removing some of the manual work that they're doing? We force all of our teams to characterize and codify what the value is going to be first before we even allow a pilot to happen.
8:04So for some folks, that's a pain because they're like, no, we just want to experiment. Like, fine, I'm okay with experimentations, but the resources are limited, right? So we have to pick our battles in terms of where do we want to invest and what does it actually mean to the business? So if I can't relate it to strategy or pipeline or contracts that we're going to go after or how we're going to be more efficient in the delivery of citizen services for the VA or for CMS or for the Air force, then the answer is always no. So I start with value first, ROI first. And if, you know, we do have a culture also that if something fails, that's okay.
8:41As long as we learn from it, and then we put those mistakes in the toolbox and we won't make those mistakes again, that's okay. But I think anchoring in value and what we're really trying to accomplish by just getting a new shiny AI tool is something that I'm really proud of this organization for leaning into. And our partnership around AI is not just my organization. We have a phenomenal CHRO who has built training archetypes for all levels of the organization. Every single person at Maximus gets trained on AI. No one is exempt. So you might have an AI user, just someone that needs to be AI fluent.
9:15You may have an AI developer, AI maker. So we have different tracks for the folks here at Maximus. And what that has done for us is it has made adoption a bit more organic versus me forcing everyone, hey, you shall use XAI tool. So certainly a long winded answer, Peter, but I will I will bring it back to it's about anchoring and value. And if we can't have demonstrable value in terms of what we're delivering, then I think we could be wasting resources in terms of in terms of AI. And that's something in these times that we just can't do.
9:52Peter High: So many interesting aspects to that response. Thank you for that, Derek. I want to talk a little bit more about the training that you provided and getting everyone to AI fluency. Surely in an organization as large and complex as yours, there were people that were leaning further forward or perhaps initially away at the change that you were suggesting. You talked a lot about culture there, which I really appreciate, the importance of the people aspects of this before even the processes and certainly the technology. Talk a bit about how you presented this, perhaps even with an eye towards the naysayers or the people who might be inclined initially to make the changes that you were suggesting.
10:37Peter High: Talk a bit about that process, if you would. Yeah, that's a great question. And I tried to paint a picture of doom and gloom, but also opportunity when I would have these conversations and the conversation, especially in our town halls, et cetera. Listen, AI is here, folks. It's going to be ubiquitous. I think we all recognize that. It's it's our job to make sure that the market dynamics and what's happening from a technology perspective outside of these walls don't disrupt us. We would rather disrupt ourselves because if we don't disrupt ourselves and make sure that we're reimagining processes, doing things more efficiently and getting more scale from the application of AI, then our competitors who are doing that will begin to take our work share in our markets, but also to grow revenue, etc.
11:32And if we're not growing, that's a problem for every single one of you. That means your teams are shrinking. That means folks that are depending on Maximus for paychecks and 401ks, etc. There's a real human component to this. So that makes folks a little bit uncomfortable, but at least it gives it makes it more personal than this is about technology. No, this is this is about our people. This is about the future of Maximus, future of your family, et cetera. So I make it a bit more personal, but it's just about the technology element. And I think that's in many cases, that's where we've gotten it right.
12:10and I've gotten a lot of feedback on the way that the messaging is carried because you have a lot of folks that perhaps had worked in a call center for 20 years. Their P &O owners are like, hey, we don't want this. We don't want this AI thing. It's going to disrupt my folks. People are going to lose jobs, et cetera. So I have to have very direct conversation with those folks. Listen, if we don't reimagine the way we're doing things, bring AI in for call summarization, et cetera, this contract that you've been working for 20 years will no longer be here because our competitors will come and say, hey, they're doing this with 300 people.
12:46We can do it with 10 and AI and we will lose that battle. So we have to be able to show on contract how we're innovating to make sure that we stay sticky with customers. And I think that's a very different conversation and gives folks impetus to say, huh, maybe I should lean into this vice trying to push away from it.
13:03Peter High: You also mentioned earlier a really important point, the notion of a failure-friendly culture, so to say. And it makes a lot of sense. If you're batting a thousand, you're not innovating. So there's got to be some failure in order to innovate and in order to sort of push the envelope further and ensure the organization has room for growth. That said, I wonder what does a failure-friendly culture look like inside a company that serves government agencies where mistakes can carry political or public scrutiny? Talk a bit about the balance between those, if you would. Yeah, there definitely is a balance.
13:37And I think the way we've tried to be responsible in that failure is we have environments and we have R &D environments. I talked about the team that we have in India where we essentially will mimic production environments. Let's say if we have a program on the VA side of things, we will essentially duplicate an environment and allow folks to go in and break things and see if this deployment of this widget or this AI tool or this new software, this new REST service is going to make a workflow better. So the way we think about it is let's reimagine the way we're doing business. And then if that worked and is proving out and we can do it in a secure way, then we have a discipline compliance framework that allows us to bring that to production.
14:28The way that we tried to incentivize failing is by doing it. And it sounds counterintuitive, but we have fail parties, Peter, where like people come to a party. It may be some some some music and some clapping for folks that had failed at a particular pilot or failed at something. And the whole idea is you're not in trouble. You don't have to go to the corner for failing. But what what your job is, the mandate is to be able to stand up and say, yeah, this is what we failed. But here's what we learned. And this is what you should not repeat, whether it be a technology thing, whether it's a process thing.
15:04So that has started to take root a bit. And that's that was a hard thing to force folks to get more comfortable with taking a risk. Because, you know, we had CEOs, CEOs at Maximus. We only had a few, but many of them came out of the consulting world, Big Four, KPMG and were auditors. So risk aversion here is a real thing. So that's a constant battle that we fight on. Yeah, we need to protect the company, but we also we cannot lock things down so hard that we're not able to innovate to take a bit of risk because our competitors are definitely taking risk and we don't want to be behind. And we want to be looked at from the government services perspective as folks that will take risks, folks that will bring commercial technology to the government.
15:59Because we understand the regulatory environment, we can do that in a safe way. So it is a constant balance, but we've created an environment where failing is OK. And by mimicking things in our R &D environments that essentially align to what we have in production, we're allowed to execute things in a way that's safe without breaking our commitments to our customers.
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17:44Peter High: And now back to the interview. Fascinating. And in multiple of your responses, you're speaking to fine-tuning that risk tolerance within the organization. As you look externally to government agencies who are many of your clients, some of them, whether warranted or not, have a reputation for being a bit more risk averse when it comes to new technology adoption. And I wonder the flip side of what you've just described in terms of the internal ways of thinking about things. How do you pitch AI-driven modernization to your customers? You articulated so nicely the way in which you pitch this internally and the necessity for the organization to change, that ultimately one's own growth in the organization, providing for one's family, the growth of the company depends upon continuing to modernize.
18:33Peter High: Talk a bit about how you, the company, makes similar pitches or dissimilar, as the case may be, to your clients in terms of the necessity to make comparable changes. Peter, it's a great question. It's a similar approach, but just a different dimension, right? So inherently, the government's job is to be able to serve people or, again, as I said at the onset, to put as much capability in the hands of our warfighters, our soldiers, sailors, Marines, et cetera, to make sure that they can protect you and I, protect this nation, which is incredibly important. You know my history as an Army guy. So a lot of times when, you know, if I'm talking to the CIO of the Army or I'm talking to one of our clients, what I focus on is it's always about mission.
19:23The technology is ephemeral, right? It's going to ebb and flow. And what I try to anchor on when we talk to customers is, look, you may have some legacy processes that are outdated. It's taking too long for capability to get in the hands of folks that need to deliver on behalf of citizens. What that means in real time or some folks, especially if it's on the healthcare side of things, may not get the care that they need, may suffer. Veterans may have a process that should take 100 days, taking 300 days. So we try to anchor in, look, your mission is too important and failure is not an option. Here's our view of the world and here's what we can do to make sure that we can improve that mission.
20:08And if your focus is speed, we can help you with that. If your focus is quality, here's how we can help you with that. If you have other requirements and what you're hearing, the signal from the folks that you are serving, they have big problems that they want to be solved. We focus on that problem and what that means to the mission by just saying, hey, we're the best technical choice. Because it doesn't matter what tech that you bring to the fight. I think what's really important is how do you leverage different capabilities across your technology state and then align that to an outcome, which even a person that's non-technical can understand.
20:46We have to be able to have conversations with folks that are doing acquisitions in the same way that we have folks that we deal with folks that are doing technical things. Because I can't go in there and talk to the acquisitions folks about, hey, this is the best architecture and you really want to go here because this tech is so cool. They don't really care about that. I think acquisition folks want to understand what are the feature and benefits that your solution or your approach is going to give to my agency and how does that work in serving the people. And I think when we anchor around that, it's just a different it's the other side of the coin in terms of how I address it internally.
21:26But it's all about making it personal, Peter, making it personal and making it about mission in a discernible narrative that folks can understand in terms of how a mission will be impacted. And I think a lot of times when we just focus on a technology side of things, you lose that. Yeah, well articulated.
21:50Peter High: Thank you, Derek. You sponsored not so long ago a defense hackathon with the National Defense Industrial Association. I wonder what did that produce and what learnings did you draw from that experience? Yeah. So our hackathon as a service was a, you know, something that, again, an innovation that two engineers, we built that portal over a weekend. And we came up with this concept because, you know, especially on the defense side of things, there's this concept of valley of death where you're doing a lot of different R &D, you're doing technical evaluations. A lot of those things are happening, but that capability never gets to the warfighter.
22:30And we wanted to create conditions where industry, the government and academia can work together solving real problems, real use cases that are coming out of the force or coming out of the government, getting folks together, solving those things, and then creating a pathway to be able to get those things on contract in the hands of people that need it. There's been a lot of experimentation, you know, across the Air Force and the Army and on the intel agencies. But a lot of times those things down the vine because there wasn't a construct to be able to move from ideation to production. So the hackathon as a service and what we're doing with NDIA is making sure that we can use partnerships to make sure we have the right use cases, the right data and the right relationships with federal customers, customers across the force to be able to take things and get it into production.
23:27because we don't have the time. If you think about the geopolitical environment, the rise of China, then we have the Iranian conflict and those things that are happening. We need to be able to move with speed. It can't take six months for us to get capability in the hands of commanders that are out in the field. So this hackathon as a service is a construct we created to get everyone in the same room. Let's solve some hard problems that are relevant to mission commanders that are out in the field and then figure out a pathway with acquisitions in a room, with programs or record folks who are managing those things.
24:05How could we do this with some speed? And I will tell you that the NDIA hackathon is not the first one we've done. We've done modern day Marine hackathon. There's so many hackathons that we now do. And I'm seeing evidence that real use cases that were born in those hackathons are now getting into production in the special operations arena and other places. So this is working, but we need to scale it up because the partnerships are what are critically important. And one thing that is very different from in the United States than if you think about some of our peer competitors, the Chinese, the North Koreans, et cetera, their incentive structures are very different there.
24:46When Kim Jong-un or when Xi Jinping says, hey, military academia, this is what you're going to go do, that's final. That's what they go do. Here, it's capitalism. Everyone has different incentive structures and folks are trying to maximize profits and we're beholden to shareholders, et cetera. So the incentives are a bit different. So we have to create a structure where people can appeal to their incentives, but also we can get capability to the folks that need it. And that's a challenge that I think we're going to continue to face because we still live in the greatest country in the world. But I think that that challenge is something that we're constantly we have some friction because what may be important to Maximus may not be important to a competitor.
25:38And we need to work together to deliver on behalf of the government. So I think leaders like myself have to have some very candid and hard conversations with our partners and other companies to make sure they are focused on what's really important to the nation and not just being self-absorbed in terms of maximizing shareholder value.
25:59Peter High: Fascinating. And I love the whole notion of partnering with the eventual users of what you're building in terms of the problems or opportunities that they are seeing. It harkens back to your earlier point to begin with value. And this idea of unusual partnerships, I want to return to something you described when you mentioned you're not my grandfather's CIO, as you put it. Talk a bit about your partnerships with Silicon Valley. I'd be interested to understand how you built out that ecosystem and how you thought about the leveraging venture-backed startups in an environment like yours to your own advantage.
26:37Yes. So it's a great question. So let me get to the left of the question first. I think we all recognize if you if you look at some of the executive orders that are coming out and how acquisition across the government is changing. It has evolved like a lot of contracts for the past decade or so were time and material or they were cost plus fixed fee, meaning you would charge the government. it. They would pay you for all the costs that you essentially have for a contract, and then they'll give you a fixed fee on top of the contract. So in a contract like that, you can have a contract for five years that's cost plus fixed fee, where you're on the hook for delivering and implementing a system.
27:22Regardless if the system is pretty crappy, Peter, you're still going to get paid for it because the contract says it's cost plus. Then you still make the fee. And when you hand over the keys, the system is already OBE because the technology landscape has shifted under our feet. What has now changed is we're going more and more toward outcome based contracts for a fixed price where the government will say, hey, yeah, we want you to deliver X system. But what you're going to get is one million dollars to deliver that system, not 10. It's not cost plus. So if you can't manage your capability, you can't manage your engineering processes.
27:59That's on you and you assume that risk. For Maximus, we we grew up as a company where 60 percent of our contracts are just under 60. Our outcome based contracts. So we're very comfortable taking on that risk. Like, I'm very comfortable with saying to government, hey, based on your requirements, we intend to deliver you a system in this amount of time and just pay us perfect unit for what we're going to do. Like, we're very comfortable there. I think a lot of our peers have not been so comfortable in that type of environment. So for us, we we'd like the fact that we have to bet on ourselves to provide better capabilities to the government.
28:46And I think we all should take a responsibility in that vice. You know, you have a time of material contract where you produce something and then you hand over the keys to the government and it doesn't do what the requirements are actually listing out. So, you know, that that is something that is being forced. If you think about, you know, again, back to the executive orders, the government wants to buy commercial. Think about Palantir and some of the other, you know, an end role in these startups that are really getting into the government and providing value. We didn't want to be on the outside of that.
29:25So the construct, the ecosystem that we create, and we have a partnership with Goldman Sachs that has a$5 billion public sector fund where a lot of different startups, like I think maybe 100 startup companies, we have partnerships with five of those portfolio companies already. The reason we partner with those companies is because we understand the regulatory environment. Think about CMMC and all of the DFARS and contractual flow downs that you have to make sure that from a data security perspective, contractual delivery, a lot of these startups don't understand those nuances. So what we've done is say, hey, we will help you gain access to the public sector environment, gain access to customers.
30:04We will help you get, you know, CMMC certified or your FedRAMP high certification, or you can bring your capability within our environment. And then we partner and go to market together to bring new capabilities to the government. So that allows us to bring Silicon Valley capabilities with speed to the government in a way that is trusted. And then the government can look at us as being responsible for making sure that capabilities are not or capabilities fit within the context of the regulatory environment and the security requirements and the compliance requirements that are out there. So that our CTO shop has worked for a couple of years to make sure that we are partnering with the right companies and bringing capabilities to market.
30:46And this is happening. This motion is live and exists today. So we are bringing Silicon Valley capabilities into our contracts today in a way that's safe. And I think that's one of the things that makes Maximus unique is because we're not trying to compete with commercial companies, the Palantir's and crew. We want to partner with you to make sure that we can bring the best of breed to the government because the government, they don't want widgets or a particular technology because I don't think that solves problems. They want solutions. So we come at it from a solution perspective. And our partnerships with Silicon Valley and our partnership with Goldman Sachs allows us to bring new capabilities at speed to the government.
31:28So that's something that we really have leaned into. And I'll tell you, Peter, it's really starting to stick. and the government, when we tell the story of how we can bring Silicon Valley capabilities to bear, we'll take the risk. That is beginning to resonate.
31:47Peter High: Fascinating. Derek, you went from running your own export business in your 20s to being a Fortune 500 CIO by the time you were 40, now two times over running technology for major organizations. Talk a bit about your background as an entrepreneur and how you leverage that experience now as an operator and a leader at scale. What do you borrow from that experience in your 20s now as a leader at Maximus? Yeah, I think a couple of things. One, it harkens back to the conversation we had earlier about failure. I'm comfortable with failure. Like, I'm OK with it. The average person will fail or get rejected.
32:30research has shown over 10 ,000 times across their lives. And the folks who embrace failure, take those mistakes, put it in a toolbox and run toward the failure as away from it. I think the byproduct of that is evolution and success, whatever the way you frame that. So there's a lot of things. I mean, you talked about the export business that I had with one of my close friends in college. Yeah, that's true. But I didn't mention the 10 other things that we tried to do, a printing business and other things that failed miserably, right? Selling things online before, you know, Amazon was as huge as it is.
33:11We failed so many times, but the export business, you know, selling things to Africa, like hydraulic systems and lubricants, That was something that was hard to get at that time. But, you know, the reason we stumbled upon that is because we failed in so many other things. And I think that's just that mindset of not being afraid to fail and being OK with it has has has served me well, because there are so many mistakes that I put in my toolbox that were a reference for me because I knew not to make that mistake again. And even in a corporate environment, I always would, if there was a hard problem, I would volunteer for it all day, every day because I like I like to do that.
33:54I like to solve problems. And I think that had served me well to help me move up in organizations, because if something was hard, I'd volunteer for me because I wasn't afraid of failing at it. I'm okay with that. And a lot of other, especially on the technical side, even just in a corporate environment, they don't want to fail. They don't want to have that target that they failed at a major project, etc. But no, I like that. I still fail today and I'm okay with it. And luckily, I have a phenomenal boss and Bruce Caswell and a leadership team that has created the space and capacity to be able to fail without being, you know, looked down upon when you do so.
34:39And I think that's something inherent in me that allows me to look at problems in a different way and also not be afraid to fall down a couple of times as long as I get back up. So a long drawn out answer, but I think the risk posture that I have personally for myself and the contracts that I have with myself relative to how how I want to serve the nation, the warfighters, veterans, etc. It's a mandate that I have for myself to make sure I'm doing the best I can to be able to serve a purpose that's larger than me. And that has served me well.
35:25Peter High: So much of your answer, I'm sure, applies to another question I wanted to ask you, which is what your military service has brought to your leadership capabilities now. I think I'm hearing the pursuing hard things, the service to your country, serving others. I assume that's the case. Are there other things you reflect on about those, I'm sure, very trying experiences, informative experiences in the military that you call upon now as a reservoir of experience and knowledge in your current post? Yeah, I think the military, there's so many misperceptions about the military. I think that the conventional wisdom, essentially, folks that are not in uniform get a bit wrong.
36:09And the thing that military, a lot of folks that wear the uniform share is the most important part are the folks that are to the left and right of you. I've had multiple deployments to Iraq and Afghanistan. The mission is incredibly important, but the most important mission are the people, making sure everyone gets back to be safe, making sure everyone has the best intelligence to protect them from harm as missions are being executed. So the people component is more important than weapons and mission and all those types of things. So I bring that same mentality to the corporate environment, too, where this machinery does not work without people.
36:50And it's my job to create environments where people feel safe or people feel confident in taking risks and then forcing all of us to have a collective goal that is meaningful. by just, hey, let's do this particular technology thing. Or it's very important that we, at least in a corporate environment, make the work more important than a paycheck. And I know everyone has to take care of family and responsibilities and bills and such, but I think it's incumbent upon leaders to make sure that there is a shared commitment to a mission that is important and meaningful. And I think the military had forced me to look at problem sets in that way.
37:43And I think that has helped me be successful in terms of doing some of the largest programs on the intelligence side of things, but also on the corporate delivery side of things, because I make sure the mission is up front and everything else is essentially just an input to make sure that we get to that mission or we get to that outcome.
38:11Peter High: So fascinating. Speaking of fascinating, among the remarkable aspects of your career, you're an author of multiple books, including one with 50 Cent. I got to hear that story. How on earth you got to know Curtis Jackson and ended up writing a book with him? Oh, my goodness, Peter. I didn't know that you were going to bring that one up. So look, let me bring that back to a failure story. Listen, I went to Virginia Tech undergrad. And my initial major was architecture. So that first semester, I learned very quickly that I wasn't equipped to build buildings. I'm like, yeah, this is just not for me.
38:51We had labs that were like five hours long. And that process, my brain didn't work in that way. Right. So then I changed to industrial design, which is essentially, you know, designing ergonomic chairs or a new vacuum cleaner or a new keyboard that you can twist your hands in a certain way that makes it easier to type. I recognized very quickly that that wasn't for me either. So there was a time where I switched to communications, a minor in communications when I went over to the business and IT side. And my focus was cinematography, film. And I had this idea that I was going to be sort of a major director that that failed, too.
39:33So I had a bunch of screenplays that I had written. That were just on the shelf. So when I graduated from Virginia Tech, I went to the army right after that. So, you know, in Iraq, you have a bunch of downtime. So I began to convert the screenplays into novels, short novellas, probably, you know, 200 or 300 pages or so. So at that same time, 50 Cent had a book line called G-Unit Books in partnership with MTV, where they had sort of these novellas that they were putting out. So that wasn't my initial target, but I had emailed, I think, 76 literary agents and said, hey, you know, I'm Derek. This is who I am.
40:22I'm an army guy. I'm trying to get into, you know, writing and authorship. So most people didn't even respond. But a person that did respond was a guy named Mark Gerald, who is 50 cents literary agent. He responded and I'll paraphrase. He essentially said, you know, I only represent folks that are that are famous or, you know, have sold a couple hundred thousand copies of different books and things. I don't really represent new authors. So I responded and basically said, hey, that's great. And I'll say the details, but I said something to the effect of, you know, I'm in Iraq right now fighting for the freedoms that you enjoy.
41:05The least you can do is read the manuscript. And he did. A week later, he emailed me and said, hey, can I send you something over there? and he did I got a lot of sent me a contract so they gave me a book deal why I was literally in Iraq I got so many boxes of stuff signed from 50 cent like lots of cds and clothes and things like that so and then one of the folks that worked for his record label became a very good friend of mine so when I got back I got to go to New York and sit sit in his office I'm sure he probably doesn't know that sitting in his chair take a bunch of pictures because he was actually and I still have those pictures but it was a very um unique experience and and I appreciate it so I still uh talk to Mark Jarrow who's still his literary agent um you know to this day and what I learned from 50 Cent is reinvention is something that you always have to do like he had a music career and acting and so many different businesses.
42:08And I think we have to, just like we talked about reimagining technology and reimagining process to make sure that you can apply technology. I think we need to do that to ourselves. And that's one of the things that I learned from him. So in the second book, I didn't want to, you know, do a novella about crime or things like that. I wanted to do something that could help folks maintain discipline, maintain contracts with themselves and have some tools to be able to become the type of person that gets to objectives that are important to them. So the second book is about that as opposed to, but it was a cool experience.
42:47But yeah, I'm a tech IT guy, not a music movie type of guy. So great experience, but yeah, that was a long time ago, Peter.
42:59Peter High: Extraordinary though. Thank you. I really appreciate you sharing that. I mean, again, it just speaks to the remarkable richness of your career and the the various things that you draw upon as a leader, these experiences, I mean, it's really a thread pulled through, through so much of what we've discussed. And I really appreciate you allowing me to pull it a little bit. Derek, before I let you go, I want to ask you as an author, especially, who do you read? Who do you listen to? Who, who, who are influential to you? I wonder for other leaders like you, who would you recommend? What's what's part of your intellectual diet that you might share with others?
43:31Yeah, I'm a big podcast guy. From a reading perspective, I'll say I read 100 books a year, but I kind of cheat. There's an app called Blinkist. Have you ever heard of the app? I have, yeah. Okay. So essentially, it allows you to get a great book. You can break it down into a 15-minute chunk or you can listen to it, etc. So I use it a lot, but I do still read full books. I read a lot about habits. So James Clear is someone that I read. I like Ryan Holiday because I like to understand the reasons for behavior. I like to understand the incentive structures that people have so I could get better at influencing folks to get to mission outcomes.
44:21From a podcast perspective, I listen to a lot of the folks that give me motivation, like David Goggins of the world.
44:34There's a lot of folks that a lot of things I listen to that aren't so positive, but I like negative reinforcement. So Jocko Willink, I listen to him all the time. And I like to hear when folks are saying, hey, you know, you're not really disciplined. If you're sitting down, you're sort of a piece of crap. You better get up and get after it. I need to hear that to make sure that I get up and go to the gym. And I have this habit where, you know, at the beginning of each morning, I do look myself in the mirror and ask myself, you know, did you give it your best yesterday? And if the answer is no, then I know I need to work double time on that day.
45:14So a lot of things that I read are trying to make sure that I can become the best me, my best self. So. It makes me better equipped to be able to serve others. So I think service is really the through line. I read a lot of Seneca. And that's something that Ryan Holiday puts out there. Marcus Aurelius, I read some of the things. I read a lot of history, lots of military history. I read that all the time. Obviously, I'm an army guy. And really, I want to read things that just help me become a better me. Because I think when you're your best self, you have more capacity to serve others. And the through line in my career is how can I be a vehicle of service to others, as opposed to just being selfless in everything that I do.
46:10Peter High: Wow, phenomenal answer. And appreciate what you've given here this morning in this conversation, Derek. It's been a great pleasure to get to know you and your story a little bit better. And I'm grateful for the time we've had. Yeah, I appreciate it. Very rich dialogue. I appreciate you, Peter. Thank you. Thanks for listening to Technovation. If you enjoyed this conversation, subscribe and leave a rating. It helps more leaders find our podcast. Thank you. And I look forward to seeing you next time. Thank you.
AI transformation should start with business value, not technology.
In this episode of Technovation, Peter High speaks with Derrick Pledger, Chief Digital and Information Officer of Maximus, about how he is reimagining work for an AI-driven enterprise. Derrick explains why Maximus defines ROI before launching AI pilots, how the company evaluates whether legacy processes can survive in an agentic world, and why every employee receives AI training.
He also discusses building a failure-friendly innovation culture, bringing Silicon Valley capabilities into government environments, and using technology to improve citizen and mission outcomes.
For CIOs navigating pressure to turn AI investment into measurable results, Derrick offers a clear mandate: start with the value you intend to create.
This episode is presented by ElevenLabs — Bringing technology to life. Learn more at elevenlabs.io
This episode is also presented by Retool — Build internal software better, with AI. Learn more at retool.com