How to Progress in Your Career as a Technology Leader

Ian Eslick is Chief Technology Officer, Enterprise Architecture and Engineering at U.S. Bank. He started there in 2019 after spending years leading a team of 180 people at Amazon. He and I spoke about leader development at U.S. Bank, and he had so many fantastic observations about what can enable it, what hinders it, and what we can do as a community to bring teachable skills to bear.

He gave advice you would give technology leaders who feel like they’ve hit a ceiling and aren’t able to progress their career, to either make a bigger contribution to the organization or to achieve their own personal goals.

Of particular interest to me was the emphasis at U.S. Bank on succession planning — after all, one can’t move to a different role (laterally or up), without having someone to replace you. He shared advice that he’s given his team on how they could replace him.

Ian provided a laundry list of skills and competencies senior technology leaders need to have and things they need to care about. It was fantastic insight and perspective about what it takes to be successful as a senior technology leader.


Ian Eslick

Chief Technology Officer, Enterprise Architecture and Engineering, U.S. Bank


Gene Kim

Author, Researcher & Founder, IT Revolution



Ian Esle. He is the Chief Technology Officer or enterprise architecture and engineering at US Bank. Uh, he started there in 2019 after spending years leading a team of 180 people at Amazon. So I met him in 2021 through Levi Gainer. And for a variety of reasons, he made a huge impression on me. Um, and only one of those re only one of those reasons being, uh, his rapid advancement, uh, within US Bank. So I had mentioned yesterday that, uh, and this morning that one of the key focuses of the programming for the next year is to explore technology, leadership careers. What best enables it, what hinders it, and what can we do as a community to, uh, bring, you know, teachable skills to bear. So I'm so delighted that Ian is here, uh, uh, to teach us, um, about his experiences and, uh, what we can do to, uh, you know, advance personal, uh, career goals, personal goals, et cetera. So, Ian, so glad that you're here. <laugh>. Can you, uh, introduce yourself and tell us about your current role at US Bank?


Yeah, thanks Jean. Appreciate it. Um, and, uh, you did a great intro, but, um, in a CTO role here at the bank, I'm responsible for our technology transformation, cloud engineering. Uh, when I was asked to take over enterprise architecture, I said, I strongly believe you can't be an architect without having an operating role. So, uh, my operating roles continue to grow in my time here. Uh, recently took over our data team and data strategy. So a lot of the infrastructure that drives modernization at the bank, uh, is in my org these days.


Uh, amazing. Um, well that observation, and I think many as awful conclude this, you can't be an architect without actually having some line responsibility <laugh>. So, uh, I asked, uh, Dr. Andre Martin yesterday about, uh, technical talent and career leadership at Amazon or Google versus more quote, traditional companies, you know, in the other industry verticals like at Nike, target, Mars, or say US Bank. Um, and I suspect that there are things that, uh, Amazon and Google value more, uh, around technology than traditional firms. And, uh, you know, I asked them, you know, on a scale of one to 10, to what degree do you think technology leaders can thrive in the non-tech giants? One is not at all, everyone should go work there. Then it's like, no, you can be just as successful. And he said 10 with a star or an asterisk, you know, that being, it may take more work 'cause you have to find that right champion. So I'd love to ask you the same question for someone who, uh, was at Amazon and now one of the top technology leaders at US Bank. You know, how would you answer that question on a scale of one to 10?


Yeah, I thought that's, that's actually well done. The, the 10 and the asterisk. So in a tech company, your management chain already knows what, you know, they know what's important. They know, uh, the value of the things that you talk about. And the reason for the star is that when you deal with the senior leadership at a different institution, they don't have any of that background. So now the bar for you to educate, advocate right, is different. You have to speak their language in order to bridge from the world, you know, to the world that they know. So while it's harder, the, the converse is you're in a target rich environment. There are so many things an engineering leader can bring to bear in a legacy organization that if you can, uh, bridge that gap, you actually can be tremendously effective and can be a lot of fun because you become someone that everyone turns to and says, well, how would we solve this? And you can, you know, kind of walk them through the opportunity.


Yeah. Um, so for someone, you know, uh, a technology leader who feels like, uh, you know, they've hit a ceiling, you know, in terms of, you know, they're not able to progress their own career, uh, either to make a bigger contribution to the organization or to achieve their own personal goals, you know, what are some, uh, lessons, uh, or advice you would give them?


Yeah, it's, it's something that comes up. I've hired a lot of folks from the outside who are technical by background and come from tech companies. I've got at least two direct reports who were senior leaders in Amazon and, um, you know, others from banks and others from large, you know, traditional institutions. So it's a real mix. And I've got some principal engineers that report to me directly that I pulled in from other institutions, both, both tech companies and non-tech companies. And so every single one of them, and including myself, have have growth opportunities. And one of the most interesting barriers that, uh, I've, I've been working through as a manager is, you know, my own background is in startups, which meant I did everything marketing, sales, engineering, leadership, fundraising. And so I forget the value of 10 years in a sales and marketing role. Um, you know, when I, when I talked earlier about engaging with senior leadership, I've realized it's all marketing.


It's, I'm, how do I translate the value of what I have to bring or what my team has to bring to something that makes sense to the audience, right? And it's something you're always doing in sales. 'cause you're the people you're selling to never understand your product as well as you do. And so you're always translating. So the, one of the biggest things we're working on and actually kicking off a whole series of workshops next year, is just taking specific problems where we're communicating to the board or we're communicating to senior leadership saying, how would you do this? And then I, I iterate with the team to work through, well, how would we actually frame this up? What, what do you think they care about so that you understand the audience? And so putting yourself in the mind of the audience is actually one of the biggest things that I'm recognizing all of my leaders struggle with.


Um, and so there's various things from workshopping to kind of bringing back what happened after I took their deck and, and cleaned it up. And I myself went through this learning curve, not so much to learn how to do sales, but to learn how to sell to this audience. You know, what matters to the CEO, to the board, to the other senior leaders. And having to recognize that they don't, they're not interested in what I know. They just want to know enough to know the trust me to do what I said I was gonna do and what the implications are for them. And so I, as an engineer, love to understand, well, the why when I was at, uh, sitting in the room with Andy Jassy at Amazon, Andy and Charlie would go super deep into issues that we were bringing to them. And I'm used to that. And here no one's interested, uh, because they don't have the background to understand it. But what they are interested in is just give me enough of a model that I understand what the impact is, that I understand the trade-offs and the costs, and then predict the future in a way that actually is right enough that I'll, I'll learn to trust you. And then you, you get actually more and more opportunities then to advocate and drive and do things because you become a trusted party.


Yeah. Fantastic. Fantastic. I maybe just, just two responses. Uh, you know, just to resonate and to riff. One is, uh, uh, in the presentation before was, uh, a role play bet, uh, of a, you know, head of technology, uh, talking about, uh, their increase in efficiency to the board <laugh> and the CFO says, perfect. Uh, well, the p and l owner says, I, I don't understand what this has to do with me. The CFO says, perfect, we can now cut staff by 5%. You know, uh, congratulations. Uh, the second one is that we both, uh, talked about how, um, you know, uh, sales training is all about, you know, understanding what matters to the person you're talking to. And it has nothing to do with, uh, uh, uh, customer acquisition. It really has to do with like, Hey, how can I be valuable to you? Does that resonate with you?


Absolutely. I'm four years into the job and I, I describe my job, uh, jokingly as half accounting, and I'm still getting my, my CPA and half psychology <laugh>, uh, or sales. And on the accounting side, it's interesting because it's, it's hard to measure things like productivity, right? In fact, we often, uh, we often talk about the Dora metrics, and so we think about things like, you know, uh, how frequently are we shipping code? What's our time, what's our cycle time through a business idea to production? And you know, it's interesting 'cause when I got here, we were just starting to exit the waterfall era. So two year projects, it was rare to see a project less than 18 months, and now we're starting to turn things around in a few months. So that's been a big cultural shift for the bank because every single one of the processes we engage with is a waterfall process.


So yes, we've gone to agile development, but finance is waterfall, risk is waterfall. You know, the, the, the audit committee comes and says, why the hell aren't you? Can't you predict exactly what's gonna happen 18 months from now? And so you have to like, figure out how to translate what we do in development to every process that we encounter, because it just creates all, all these really interesting frictions. But on the, on the value argument, it's, it's generally trying to figure out what people care about, what we can measure, and, and trying to weave that back into a story so we can deliver the value that I might be able to see, but in some cases, I still struggle to articulate the value.


So you had mentioned one kind of key skill that, uh, you would recommend, uh, and, and actually have recommended to your own teams. I one around communication, you know, uh, quote sales training and so forth, just to give a name. Uh, you mentioned some other skill, uh, which was around finance, you know, uh, around capitalization, so forth. Can you say more about that?


Yeah, it's interesting. I've, I've got a, a couple of leaders in my organization who it's like, well, it's not my job to understand finance, but at, but at the bank value as always, and I saw, I heard this when I was coming in on the end of the last call, right? Value gets translated to dollars. So I'm gonna put these many dollars in in order to get these many dollars out. And that's actually how the company used to think about every project. So they're running three, 400 capital programs anywhere from 4 million to 400 million, right? And so if you think about the world of our managing committee, they're like, well, I've got 200 projects. I'm gonna get 30 minutes a quarter with your project, your project's $200 million investment in some technical thing. And you know, so explain to me in 30 minutes what the value is, how you're doing, you know, what's going on, what the issues are, and then I'm gonna go on to the next a hundred projects over the next quarter before I talk to you again.


And when you put yourself in, in those shoes, you know, there's really only three or four things that are gonna take away from that 30 minutes. So what are the most important things to communicate? And what, what I see is that when it gets into the details, you have to work with the finance team to get to that presentation. And the finance team is gonna care about, well, if I'm spending money on something that's not characterized as capital, then that is gonna mess up, right? My tech credits, which is gonna cause me to miss my budget. And keeping your budget healthy and clean is a fundamental value and an expectation of senior leadership. So it's, it's a long-winded way of saying that you gotta watch the, the, the sort of nickels and dimes and demonstrate that you understand the trade-offs that you make and how you operate, you know, have a big effect on how the company is able to meet its quarterly objectives financially.


And what's interesting is, in a tech company, we don't have to do that. Now, one of the things that's particularly interesting about banking is it's a value company. So it's all about cash flow, and we're judged on how efficiently we, uh, leverage our cash flow. So if you pop up a little bit, even if it's to drive growth, the company gets hurt, which means it's harder to grow through acquisition. So you understanding those business dynamics took me a year or two to start to say, why does the company get so upset about X and then working backwards. So I spent a lot of time trying to educate my team on these things that I've learned, uh, and sort of walking through, you know, here's why the company does what seems crazy to you. But when I was at Amazon, Jeff would be like, yeah, I'm just not gonna have earnings this quarter 'cause I'm growing market share. And the market's like, great, here, let's push your stock up <laugh>. But if you did, but if you did that at a bank, right, our stock would collapse.


So it drives a lot of behavior through the organization. And, and so there's always, um, the last thing I'll just say this is, that's something I found really important. 'cause when you come in, it seems crazy when you come from a technical organization the way and a growth oriented organization. But as I've unpacked it, there was a principle at, at Amazon, so, uh, the principal engineering community had a series of sayings, and the first one is respect what came before. And what it means is you wanna, everything that you see was done by smart people trying to solve a problem, right? It's to, to achieve an end under constraints that you're not aware of. And so, even if it seems nuts, there were good reasons for why it was there. So a lot of my pitches, you know, hey, we've optimized to manage risk, but there's a way to achieve our risk outcomes while also accelerating our velocity. I believe we can both win, but it means we gotta think differently about how we solve the problem. So understanding where the organization's coming from and what it values is essential to being able to solve the problem. Otherwise, you're shouting at the wind because you're not aware of the constraints of the problem you're solving, and that's not good engineering.


Uh, this is so fantastic. And so suppose I were, uh, in your organization and I feel like, uh, um, you know, I, I want to make a bigger contribution. I wanna take on a larger responsibility, and yet that avenue isn't open to me. In fact, I might even think like, uh, you know, the organiz doesn't, station doesn't want me to grow. Uh, that will be your response and, uh, and some advice that, uh, you would give me.


Yeah, I do, I do this a lot. So a lot of it is, is one is to understand why do you want to grow? Like really getting into, and, and Jean, I do have openings by the way. No, <laugh> <laugh>. Um,


But, but you know, it's, it's, if you think about where you want to go, it's like, do you wanna have more impact? Do you wanna solve more problems? What kind of things do you wanna work on? So I've got some people who are in the technology side is like, I'd love to move to the business side. It's like, all right, let's find opportunities where you can deliver so you can lateral and then grow in the meantime, let's look at those skills that we get you up to the next level. So, you know, I think it kind of comes back to some of the things I've said before. The first thing that I, that I look for is, what are opportunities to get visibility to the parties that ultimately have a say in whether you progress? So in our particular environment, um, you're not gonna make a lot of progress up the rank, especially at my level and above.


Um, if you don't have strong support from the risk organization, because your ability to manage an organization and not create risk for the company is essential. So do I trust you in front of the regulators? Do I trust you to get everything right when there is a mistake? Was it because you, you weren't doing it right? And so the little things matter a lot more here. So I said, number one, you gotta keep your nose clean. So finance and risk, you gotta get that. And if you don't get that right, then it's gonna take you a year or two to earn back the trust and you know, that's gonna take you longer to progress. The second one then is communication. So do you know how to communicate to the next people up so they feel like they get value in their time from you and that small amounts of time have high bits of value and you, you were able to reliably predict the outcomes or the barriers to those outcomes so that you predicted ahead of time the problems you were gonna have. Those are probably the, the two things, right? You have to make sure that all the different parts of the company are comfortable with you and that the people you're gonna serve in your new role are, you know, getting what they need.


And you said something, uh, remarkable notable about, uh, succession planning, and I thought it was interesting to, because it was such a, um, uh, contrast to the notion like, uh, no, there's, uh, there's no appetite for leaders <laugh> and new leaders and, uh, to take on more responsibilities. Quite the, uh, opposite. Could you say more about that?


Yeah, the, the US bank does a really good job of thinking about just responsible management. So, you know, if I always have to think about what's the risk to the company, if I end up having to take six involuntary months off or, uh, you know, infinitely number <laugh> of involuntary months off and under those conditions, then, you know, if I'm the only person that can do things, then I actually haven't done my job of ensuring the company's continuity planning. So every year we do an exercise of looking at all right, you know, do you have a temporary backfill, a permanent backfill? What would you, how would you recommend the organization deals with the change? The other part of it is that we're always looking at opportunities. When a big problem comes up in an area, it's like, well, what leaders can we move into that area?


So part of building those relationships I talked about earlier is about getting yourself ready for when the opportunity comes. And, uh, so, so in succession planning, I always make sure I have two people who could conceivably do my job. And then part of the coaching is I let them know explicitly you're in my succession plan, doesn't mean that you're going to get my job at any particular point in time. 'cause I may not leave it. But in the meantime, <laugh>, you know, how do we get you ready in case I do? Right? So in my case, the, the, the only job up from where I am is the head of all technology for the bank, and that's on the managing committee. It's a, it's a fairly high visibility, regulatory function and a lot of, uh, out talking to the street. So there's a lot of growth that I would have to do to be in my boss's succession plan and, and to prepare for that.


So partially what he's doing for me, just to give a another example of being on the other end of it is, alright, can you talk to the board? Can you talk to the CEO? Can you make your case? And so my my coaching, uh, from the, the, my boss's previous boss was, uh, number one, you spend way too much time explaining things. People don't want the explanation. So how do you get it down to three bullets, right? And that's struggle for me. So I, I know as I've been practicing, it's actually really effective if you can get it down to a pithy Twitter, like, you know, essence of the issue. Um, that creates a mental model that people can engage with. And so over the last couple of months, I've had more opportunities to do that, and it's effective, which means, uh, people are getting comfortable, okay, I'm comfortable putting you up in front of the board for a bigger issue and, and so on. And so you slowly earn trust as you earn trust and deliver right against the things that you said. Then those opportunities start to open up.


Oh, <laugh>. That's great. Uh, Ian, um, I, I get so much out of every interaction that we've had, and I so much appreciate you taking the time today to share your, uh, lessons learned wisdom with, uh, this community. And I, I so much look forward to the continuation of this, uh, looking into 2024. Uh, thanks. Thank you so much, Ian.


Yeah, thanks Gene. I really love this series in part, you know, I was talking to Paul at, at the conference a couple weeks back, and one of the things that I think would be really powerful out of this series is starting to distill down the, you know, as a manager, building my succession plan and growing those leaders to break through the glass ceiling in organizations like this. You know, kind of what are some of the, uh, both practical experiences you can put someone through, but also just some of the, the training. How do you give people the mental models so when they encounter these situations, they've got an idea about what to try and how to act, you know, and how to, how to experiment and, and, you know, fail, uh, without, uh, you know, with Grace, <laugh>,


<laugh>, uh, ideally, uh, before the production environments in planning and practice, yeah,


Not production. You have to, you have to find, uh, small mistakes, small mistakes that you can make and learn from.


<laugh>. Very good. Ian, thank you so much. I'm looking forward to our next interaction. Uh, let's make it sooner rather than later. <laugh>,


Look forward to it. Gene, thank you. And thanks everyone else. Thank you Ian