ESI Interviews

Ep 6: Pushing the Envelope Without Breaking Things with Box Global CIO Ravi Malick

Guest Michael Keithley
Ravi Malick
April 27, 2022
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Ep 6: Pushing the Envelope Without Breaking Things with Box Global CIO Ravi Malick
ESI Interviews
April 27, 2022

Ep 6: Pushing the Envelope Without Breaking Things with Box Global CIO Ravi Malick

On the sixth episode of Enterprise Software Innovators, Ravi Malick, Global CIO joins the show to share his view on how large enterprises can best partner with startups to lead new technological initiatives, the importance of operational, back office innovations for CIOs, and the best way to build successful leadership teams.

On the sixth episode of Enterprise Software Innovators, hosts Evan Reiser (Abnormal Security) and Saam Motamedi (Greylock Partners) talk with Ravi Malick, Global CIO at Box. Ravi’s career has taken him from investment banking and consulting to the energy industry, where he spent nearly 4 years as the SVP and CIO of Vistra Energy before landing at Box. Evan and Saam speak with Ravi about the most defining moments of his career, the operational differences of startups vs. Fortune 500 companies and how they can work together, the best ways larger companies can leverage startup-driven technology, and the roles of CIOs within executive teams. 

Quick hits from Ravi:

On finding the balance of innovating while maintaining a solid foundation: “Your ability to change is determined by the business’s ability to absorb it and how much can you push the envelope a little bit without breaking things”

On recognizing the correlation of company size and operational speed: “I went from being in a speed boat to a tanker”

On prioritizing the importance of experimentation within organizations: "You have to constantly experiment. If every day you’re worrying about the current project, and the current issues, you're going to miss the opportunity...I always felt that if you use technology effectively, [the company could] jump four or five steps ahead."

Recent book recommendation: Flash Boys: A Wall Street Revolt by Michael Lewis

Episode Transcript

Evan: Hi there and welcome to Enterprise Software Innovators, a show where top tech executives share how they innovate at scale. Each episode covers unique insights and stories that will help you succeed as a technology leader. I’m Evan Reiser, the CEO and Founder of Abnormal Security.

Saam: And I’m Saam Motamedi, a general partner at Greylock Partners.

Evan: Today on the show, we’re bringing you a conversation with Ravi Malick, who recently became the Global CIO at Box. We spoke with Ravi before he started his new role, when he was coming off close to four years as the SVP and Chief Information Officer at Vistra Energy. 

Vistra is a Fortune 500 company and one of the largest electricity generators in the US. With over 5,000 employees, they provide electricity and natural gas to over 4 million customers.

Please enjoy our conversation with Ravi Malick.

Evan: So in 2010 you joined TXU Energy, a company that eventually became part of Vistra Energy. This was after you had worn a ton of different hats in finance, consulting, tech, and, if I’m not mistaken, a startup, too. Can you tell us what it was like getting started at TXU?

Ravi:  You know, as I used to say, I joined TXU energy with like, a three, four year plan, and it ended up being over 10. And it was quite frankly, one of the most rewarding phases of my career. I learned a lot, learned a new industry, a really interesting and complex industry.

We were in a Fortune 500 company, but there was a lot of startup feel to it. You know, we were building things and doing new things and testing new things. And emerging from bankruptcy, we did acquisitions, major acquisition to double the size of the company and take it from a Texas company to a national company.

And we followed that with two more retail acquisitions. And through that, we were trying to, you know, move everything to the cloud. So it was like, it was pretty fast paced. And there really wasn't much of a dull moment ever.

Evan: Wow, that's an amazing story. You know, personally, I’ve been really impressed by the speed of innovation at Vistra. I guess as a quick follow up, you know, was there some individual person, or what really helped you define your style of leadership as CIO?

Ravi: Yeah, I think there were a number of people that influenced me during my career. I tried to take the best aspects from the leaders that I respected in addition to reading things. I'm a huge Patrick Lencioni fan. One, because the books are really easy to read.

And two, they make sense. They're very practical in nature. You take what you can and apply it. I've always tried to be a believer in people and that people like to be empowered and like to get credit and you know feel supported and feel safe in what they do.

You know, they like to understand why they're doing things and I think the folks that have influenced me in a lot of those ways and shaped my leadership style are the folks that have enabled me and empowered me and trusted me, a lot of times in situations where I might not have really known what I was doing, but they knew that I would figure it out and I’d dive in and, you know, roll up my sleeves. I think what I learned, one of the most significant things that I've learned in leadership is it's important to make decisions. Lack of decision is almost worse than a bad decision because you can always course correct. 

That's probably one of the things that - that may have distinguished me is that I'm comfortable looking at risk, assessing risk, and then kind of very quickly making a decision. The CIO that brought me in - I was probably a little bit naive to big company politics, and so he was someone who really attuned me to thinking more broadly and thinking about the stakeholders and, how do you communicate?

How do you work with people and through people that, you know, you don’t have authority over, in order to get things done. And moving quickly and getting that communication out very quickly. You know, it's effectively selling.

I mean, he was basically like, you've been in sales, you've run sales teams, you gotta sell. As a CIO, you're constantly selling, you're selling your ideas. You're trying to close on your ideas and get the yes. He really helped cement that understanding, not necessarily, you know, playing the politics games, but really just understanding like, okay, who are the people that are going to be the decision makers, who do you need to know to get on board? Who might be the passive aggressor in situations and, making sure you're always covering your flank.

Evan: So one more follow up on that. You talked about decision making and collaboration in larger organizations. Were there any particular moments where the light bulb went off for you? And ultimately what led you to those beliefs?

Ravi : I think it's when I realized, I went from being in a speed boat to now I'm in a tanker. So my planning horizon had to be extended pretty significantly, right. Smaller company, hey, we can make a decision. We can pivot, we can move in two weeks, maybe a month, 45 days probably would have been considered long to ah, you got to think in six month terms. When your annual - your financial planning cycle is done in five to seven year chunks, it kind of gives you a feel for, okay, you know, I got to think a little bit longer from a planning perspective. Cause you know, instead of moving you know, or getting a couple hundred, 300, 400 people to move, you're trying to get 8,000, you know, 10,000 people to move.

But in situations with some of the smaller areas and more niche areas where we had leveraged startups. Those are things that we might do in months. You know, there's a balance of you've got to think the long term, but you've got to recognize the opportunities where you can very quickly drive value in the short term.

I’m trying to remember the exact moment where it clicked for me. There was a change, there was something I was trying to do early on. And it was in SAP that I'd spent some time with the call center agents. I was like, oh, you know. It's so simple!

If we make these three changes it's no problem. And I was like, okay, when can we do this? Can we get this done for this month's release? And people were like uh no [laughs], that's gonna take about six months. I was like, what? And then it was like six months and then you've got to roll it out.

You’ve got to get with the call centers and you've got to get with marketing. And, you know, I was like, okay. I think I've just realized the magnitude of the vessel that I'm on.

Saam: It’s really interesting talking about how the velocity changes as you go through these different organization sizes. I wanna double click on that and also what you were talking about at the end, in terms of working with startups, Ravi. I think one thing that has always stood out to me about you is, on the one hand, you were leading IT and technology at one of the largest Fortune 500 companies in an important vertical in energy that's regulated and mission critical and has all of the gravity associated with that.

And on the other hand, you frequently have partnered with technology startups very, very early on in their lifetimes. Talk to us about your framework for how you decide when and why to partner with startups and early stage companies, as opposed to more established sort of legacy players.

Ravi: What it comes down to, I think, is being able to leverage technology at an early stage, and quite frankly, have a lot of input into how the product is developed, and have the ability to shape it for your use. That kind of feedback into the product life cycle from a customer, particularly a Fortune 500 customer, that's using it and pounding on it every day, I think is invaluable to a startup.

This is good. This isn't good. Here's what we're thinking. Here's what we need. And having that direct line, it's hard to do that with a large software company. And, you know, the other aspect of it, quite frankly, is I'm kinda cheap. [Laughs] There's value in being a first mover.

Getting things on the cheap. And just looking at it as you would look at any asset, if the asset is undervalued, from a market perspective, and I can pay less knowing that there's tremendous upside. Why not do it? I'm perfectly comfortable doing that.

And we had several examples where that was the case, where we were early movers, early adopters. And, the value that we got was pretty outsized compared to what we were paying for.

Evan: So Ravi, when we’ve chatted in the past, you've used this kind of financial risk versus reward model to talk about the assessment about how you make these kinds of investments. Can you talk more about the trade offs between capitalizing on some of the upside opportunities versus mitigating the risk of working with maybe less mature, and in some cases, you know, less stable companies?

Ravi: Yeah, I think, the risks with early stage companies and certainly, in the energy business and probably a lot of other well-established, traditional businesses is, I think a lot of the risk is misconception. You know, it's misconceived what the risk is.

And you hear things like what if they go under, right? What they go belly up or what if they get acquired or, and those kinds of things. Which, if you think about it, realistically, that risk exists really with any business. It's probably a little bit more in some early stages, but the diligence that we do or that we would do in those situations is we would really look at okay, who's funding it?

You know, are they early stage? Anything that was really earlier, pre-series A, would have been tough. What's the history of the founders? We looked at, or certainly I looked at it similarly to how a VC would look at it. I'm going to invest in the software and invest in it for the company with the expectation that there's going to be some level of returns, some value associated with that.

Saam: So, I want to follow up and ask about the other side of risk reward, which is driving an organization's culture. What did you bring in and drive from a culture change perspective at Vistra that’s enabled this type of risk-taking and acceleration? And for those of us listening, what are a few things you'd recommend that people do from a culture perspective that would enable this type of risk taking? 

Ravi: That's a tough one. I don't know how much influence I actually had on the culture. [Laughs] That industry has a very well-established and very well entrenched kind of approach and culture. At the end of the day, what I would say is, look, the technology is going to work, right? You can get technology to do whatever. If you have concerns about two things being integrated, we can figure that out. You can solve for those things. And even if it's - if that solution isn't necessarily very clear presently, give it a few months, right? And that's how fast things are moving. What I would hope is that I left the understanding that you have to constantly experiment. If every day you’re worrying about the current project, and the current issues, you're going to miss the opportunity. And I always felt that you could use technology to skip four or five steps, right? Not one or two. If you use technology effectively, I could jump four or five steps ahead.

And yeah, there might be a little bit of risk upfront and there might be a little bit harder work, but the end result - my expectation was we're going to be that much further ahead. It didn't always work out that way. But I think for the most part, where we made some big bets, they definitely paid off.

Evan: So Ravi, you talked about building a culture of experimentation, right, in technology. Let’s talk about the energy industry for a second. The Vistra brand is relatively new, but the company has roots that are over a hundred years old. I think most people wouldn’t assume that the energy industry is a place where you really want to be experimenting a lot, given the mission criticality. Could you talk for a second about, you know, what is unique about the CIO role within the energy industry?

Ravi: Oh boy, what is unique? Well, lots of regulation. [Laughs] I think certainly what was unique at Vistra is you have a incredibly physical side on the generation side and incredibly safety oriented. Lives can be lost in that part of the business. And so you have to think about change in a very meticulous way.

You have to be mindful of what that change could potentially impact. The industry isn't - particularly in the fossil fuel generation - isn't really at the point where, you know, you have full automation at the plant, you're truly replacing humans a hundred percent.

So, you know, the impact of technology to the extent where it could have a life impact isn't quite as great. It's probably gonna get there at some point or is starting to. But certainly, implementing change at the plant level, the experimentation was something that there - there was far less wiggle room.

Flip that to, you know, our retail side and the customer side, where the market is, every day you're competing for customers, right? It was essential to experiment there. Essential to make sure that you're listening to your customer base, roll out change fast, and do things that, you know, were going to have a value for the customer base. So what we tried to do was take things that we learned there, and experiment in a way that we would be able to take some of those concepts and use them in the, on the generation side.

What was really interesting is that there are a lot of capabilities that were shared and similar across the businesses. And that was one of the things that we learned being on the technology side, you could see you're developing something over on the generation side that is pretty much the same as the retail side.

Like why are we not leveraging that? And so, you know, we made a concerted effort to recognize what are the similarities, right, and how are you using data? You know, the other, the unique aspect of being a CIO in that industry, is that, you know, there is a fair amount of regulation and depending on what your fuel mixture is for your fleet - 

If you've got nuclear, I mean, nuclear’s like - put that in a whole different category on its own. Coal, natural gas, these plants all operate very differently, right? A coal plant, conceptually how you generate power is basically the same, but the moving pieces and moving parts can be very different. Right, and then you’ve got battery and solar starting to move into the mix, completely different animal. It's almost like you've got multiple personalities that you're dealing with as a CIO. The guys at the plant, what they care about is safety, nuclear is all about safety, right? Clean room, you know, procedures, process, making sure that everything is done very meticulously.

And then you got retail, which is much more technology dependent, much more technology invested, really pushing on the digital side of things.

You got to find that balance in the different speeds and how fast you push things, cause I think in any scenario, your ability to change is going to be determined by the business's ability to absorb it.

And how much can you push the envelope a little bit without breaking things? A lot of times it felt like, you know, I'd have one conversation and we're in the 21st century and then I have another conversation and like, I feel like I went back 20 years. Like we're just trying to get basics in place.

Evan: So Ravi, let’s talk about how you apply that, right, when you’re trying to build a leadership team inside the organization. You know, the job sounds very challenging because half the team is about going slow and being safe. And the other half of the business is about going quickly and innovating to make sure you’re adapting and evolving to really outpace the competition. So when you think about building a team, and building the decision making systems, and building the culture, how do you get the best of both worlds?

Ravi: It was probably less about thinking about how I get the best of both worlds versus, how do I get the best people, the best leaders? Like what are the leadership qualities that I'm looking for? What is going to make somebody successful in our environment?

How do they work with people? How do they think strategically? How do they execute? I think with any leadership team, you know, you're obviously trying to build a cohesive team that works well together and recognizing the strengths and skill sets. And I think first and foremost, recognizing your own strengths and limitations.

And maybe not necessarily trying to turn your weaknesses into strengths and spend a lot of time there, but really trying to hire and fill your leadership team based on your own weaknesses. For me personally, that was operations and kind of that day-to-day grind, and the details of that stuff, it's just, it's not something that, you know, I wake up and go, that's what I'm super interested in. I get up thinking, like, I'm thinking 18, 24 months out, right, what's the next thing, what do I need to be thinking about? In terms of the business, where's the business going and how's technology gonna match that? Where can we leverage it to accelerate progress and competitive advantage?

So I always know, I have got to have somebody that is meticulous in the details on execution. That knows how I'm going to track this every day. And I'm going to monitor it every day, and I know what I need to look for and I'm going to report back. And can have the discipline and methodical nature to make sure that you're executing and delivering with consistency. 

I think one thing I - I've learned over the years is that. You have got to have your ops nailed down, right? You can't build on a shaky operational foundation.

And I think, again there's balance, right? So sometimes you're growing and you've got to have the ops catch up. Sometimes you get a little beyond and then the growth is catching up. But I think one thing that I discovered being in IT and talking to colleagues and CIOs in general is that often, you don't hear a lot about the operational side, right?

All you hear about is the innovation and we built this and we did that. But you don't hear about, I took my infrastructure outsourcing from 20 million to $0. And from, you know, 300 people to zero. Well, how'd you do that? Well, I innovated to do that. So I think operational innovation can be just as important as the business innovation, right, or the revenue or growth innovation. You know, I spend a lot of time hammering on that. Like we've got to get the blocking and tackling nailed down because I don't want to worry about it. And that was pretty, you know, it's kind of a personal thing. Like I don't want to have to think about things, I don't want to have to get involved in daily issues and be the fireman because that's not particularly what I'm interested in. It's not my strength. So I know having to focus in that area, because of how I'm constructed is how I need to build my leadership team. You know, similarly, if I had a whole bunch of people that all they did is think strategically, like we'd be screwed, you’d have outages every day. Finding that balance and knowing the personalities that you have. And making sure the voices are heard, right?

And giving people the opportunity to feel safe to raise your hand and express their concerns about an issue or express a new idea. Similarly, if you have too many ops folks, you don't get to innovate. Striking that balance in diversity of opinion and thought on the leadership team, I think is incredibly important and really spending the time to guide and coach. I think it's one of the most important tenants of leadership regardless of the role. But, you know, I think CIOs - because there's sort of this view of being the IT guy, being techie, right, you're techie, you're techie, you’re techie. There sometimes I think tends to be an over-pivot or over-weighting on the tech knowledge and experience versus the leadership knowledge and experience, right? That I can coach. I can groom my successor. I can bring people up. A lot of times the mistakes you see at software companies. You see it in IT shops is that the folks that are super smart in technology get promoted to management. And sometimes that works, sometimes it doesn't, but a lot of times, you have folks that are - they may not even necessarily want to manage.

They just, they enjoy being a technologist and developing and writing code. And you've got to look for that right blend, too. And ask people what they want, what do they want to do? You know, it's the balance of understanding the characteristics of people and putting the right mix together.

Evan: Thanks, Ravi, that’s really insightful. So in the last few minutes, we’re actually going to go into a lightning round of questions.

Saam: I'll kick off the first question, which is if there's a listener out there who just started a new role as a CIO, what would your advice to him or her be about what to get done in the first four quarters and how to put a win on the board right away.

Ravi: First and foremost is learn the numbers, learn the financials, understand the balance sheet, where you have risk and where you don't have risk. I think the next thing is start meeting with your colleagues. Go meet with the colleagues and figure out what are their top priorities.

You know, ask them for their list of five, focus on the list of two and start looking for common themes. Do multiple people have the same - same items on their list. And then start knocking them off. Set the agenda, communicate that. Hey look, I've gone and interviewed the executive team and I've gone even one level further.

And here are the common themes that I've discovered. Here's what I think should be our first two things that we go tackle. And keep it simple. The research on prioritization, and one to two things and the success rate for accomplishing one to two things I think is like 90 percent. When you start getting to three to five, it drops massively, I think to like 60. Beyond five, and success can be defined differently, but accomplishing it really, truly accomplishing it. It drops dramatically. So find those one or two things, communicate that and say, look, these are the two things that we're going after. 

Evan: Ravi, what do you think is the biggest mistake a CIO can make, or what is a common mistake that people fall into, especially for people who are new to the role?

Ravi: Assuming that everybody's on board with your ideas, that it just, that it makes sense, right? That we should do this. I think not listening. Probably the biggest mistake, not taking the time to go out and talk to your colleagues, talk to your user base and get that feedback and look at it and understand, okay, what is the data telling me?

You hear it all the time that IT knows - thinks they know the business better than the business and IT just wants to put in new things. I think the more you can avoid those stereotypes and distance yourself from them, the better.

Saam: My next question is a more personal one, what's a book you've read recently that's had a big impact on you, Ravi?

Ravi: There's a book called Flash Boys. Great book. It just reinforced the thoughts on plumbing, right? You know, the importance of thinking about your business in terms of speed and performance.

Evan: That’s a great example. Maybe as a final one, how do you think executive teams should evaluate the performance of a CIO?

Ravi: It comes down to business value. It's going to vary by what the top priorities or top initiatives are, right? So I think your performance evaluation on a year where you're doing a major ERP implementation might be different than a year where you're more optimizing.

User satisfaction comes to mind, but I think that's one of many measures. I do think tying it back to business value, okay, what did we do from a technology perspective that really made a difference and either helped us maintain competitive advantage, or helped launch a new product.

Or solved a major issue. You know, a lot of times CIOs tend to get measured purely on cost, cost management. And I do think that is something that you do need to look at. But I think evaluating on ability to appropriately set expectations, deliver consistently, articulate when things are not going well.

And evaluate them on the things that they say no on. [Laughs] I think it can be very difficult. And what I mean by that is, what are the things where the CIO says, not now, let's talk about it, maybe we'll put it on the roadmap, right? How well do they navigate through those difficult challenges because things are always coming at you.

How well do you prioritize the things that you can do from a technology perspective with the strategic goals of the company?

Saam Motamedi: Ravi, I’d like to really thank you for joining us. Evan and I have both really looked forward to having you on the podcast. You have such a unique vantage point, given the different journeys you've been on, and I'm just so excited our listeners will get to hear from you. 

Ravi: Thank you guys. It's been fun. I've enjoyed it.

Evan: Thanks, Ravi.

Saam: That was Ravi Malick, Global CIO at Box, and the former Chief Information Officer at Vistra Energy. Thanks for listening to the Enterprise Software Innovators podcast. I’m Saam Motamedi, a general partner at Greylock Partners.

Evan: And I’m Evan Reiser, the Founder and CEO of Abnormal Security. Be sure to subscribe, so you never miss an episode! You can find more great lessons from tech leaders and enterprise software experts at

Saam: Enterprise Software Innovators is produced by Luke Reiser, Josh Meer, and Emily Shaw. Our engineers are Mathew Passy and Marisa Ewing. See you next time!