Finding business value in unexpected places with Steve Comstock


This week I’m joined by Steve Comstock who is the Chief Information Officer for CBS Interactive. Steve is not your typical CIO and brings a very unique perspective.

Our conversation takes a markedly provocative look at the changing CIO role from technology focus to business partner. We discuss the relationship between Shadow IT and the Rosetta Stone and how humility plays a role in failure. During our discussion, we push boundaries on how the CIO as a technologist is no longer a differentiator and how the CIO evolves to the COO and CEO roles.


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Podcast Episode

Episode Transcript

Tim Crawford:               Hello and welcome to the CIO In The Know podcast, where I take a provocative, but pragmatic look at the intersection between business and technology. I’m your host, Tim Crawford, a CIO and strategic advisor at a Avoa.

Tim Crawford:               This week I’m joined by Steve Comstock who is the Chief Information Officer for CBS Interactive. Steve is not your typical CIO and brings a very unique perspective. Our conversation takes a markedly provocative look at the changing CIO role from technology focus to business partner. We discuss the relationship between shadow IT and the Rosetta Stone, and how humility plays a role in failure. During our discussion, we pushed the boundaries of how the CIO as a technologist is no longer a differentiator and how the CIO evolves to the COO and CEO roles.

Tim Crawford:               Steve, welcome to the program.

Steve Comstock:           Thank you, Tim. It’s a long time listener, first time caller. Super excited I got through.

Tim Crawford:               Great. Glad you made it and let’s just dive right into this. You and I have had a number of conversations around some pretty provocative topics over the years. One of those happens to be with the CIO role. You’re the CIO of CBS Interactive and we often talk about the CIO role and how it’s really different. I want to kind of jump in with what’s your take on how things have changed in the CIO role from years past to today and moving forward.

Steve Comstock:           Yeah, thank you. It’s interesting. I heard this at a conference the other day and I couldn’t agree more is in the past, we were just plumbing and I remember ages ago, a financial planner had called me up and asked me what I did for a living. He goes, “Oh, you’re going to be a VCR repair man in about two years.” And it was kind of insulting, but he wasn’t too far off. We were just, hey, you’re the guy who would go to for a PC, WiFi, you’re the guy who can get me a power cable. Right?

Steve Comstock:           And I think the change is, especially in some organizations, and I can’t say it’s in all, but a lot of the transformation organizations, you actually are part of the overall team. And you play a very, very specific role, and it’s not the guy with the power cords, it is anything from defensive lineman to an offensive lineman, depending on if you’re doing security or if you’re trying to break into a market where your business partners are really going to count on you to do your job and really contribute to what should we do and how should we do this? Take the big idea and go with it, which is really a fun and exciting change and it’s kind of fun to watch who can adapt and who can’t because if you’re sitting there handing out power cables for 15 years and then someone says, “Hey, we want to do streaming the Superbowl on 12 different platforms with potentially 4 million concurrent streams, hey, you got about six months, how are we going to do it?”

Steve Comstock:           And he can’t go down. I was like, “Oh yeah, cool. How are we going to do that? How are we going to test it? What do we need to do? What sort of organizational things do we need to put in place cetera.” Or looking for those opportunities to improve the overall revenue stream, whether it is improving the customer support experience or improving the pipeline for sales or optimizing the logging of the pipeline for sales or metrics around sales or whatever. We normally wouldn’t have been part of those conversations and we’re starting to get included in those as people are realizing we can add a lot more value than just power cables. Right?

Tim Crawford:               Right. Yeah. And when you talk about the streaming, you’re going to need a few more power cables then you probably have in the kit.

Steve Comstock:           Yeah. Yeah, exactly. And a lot of Xanax.

Tim Crawford:               And a lot of Xanax. When you think about how you’re engaging with customers and how you’re building those relationships with the rest of the C-suite, I mean, going from power cables to figuring out a new business angle or a significant change is not a trivial step. I mean, you and I were involved in a recent conversation amongst a group of CIOs talking about customer engagement. How do you start to think about where do you get started, how you build those relationships, so that you’re prepared for those questions that are going to come your way, but then you also have the relationships in place where people think of you more than just a power cable dealer?

Steve Comstock:           Yeah, absolutely. It’s really interesting. And it was quite a transformation for me. When I talked four or five years ago at a keynote about shadow IT and everyone was like, “shadow IT. Oh.” But my point of view on it was shadow IT is really like the Rosetta Stone of technology today. And if you don’t know the Rosetta Stone, there was an emperor ages ago. There was three different languages in his province and no one could understand each other. So they basically put one language on one side, translated it to the language on another side that translated to another side and one of those languages. One of those languages was hieroglyphics. And that’s how we were able to translate hieroglyphics. Right?

Steve Comstock:           So if you take business need, business value and make that hieroglyphics or maybe it’s the tech that hieroglyphics and it’s everybody else is speaking their language, but I was using shadow IT at some level where I’d see it and say, “Hey, help me explain, what are you trying to do, how’s this help your business?” And really just be engaged in the moment with my partners and I think this is a keyword, my partners. Not the business, not the customer, my partner because we’re in this together. Our checks say the same thing and really sitting down to understand how does their business work? If they’re the tight end on the team, how do they run their route and why do they run the route that way?

Steve Comstock:           And if I could help, maybe they could run around a different way or taking the whole football analogy. And by the way, I know little to nothing about football, but I’m going to run with it. If I’m the right guard and I know the tight end’s going to do something, if I can maybe shift my movement and block for that person to help them be more successful, that’s my job. And you build that trust by doing that over and over and over again.

Steve Comstock:           And it really is a very humbling and transparent thing that you have to do where I will walk into an office of someone and I know I screwed up. I know I made a huge [inaudible 00:07:15], a huge error, and I will come to them before they come to me and say, “Hey, you know what? I screwed up and this is probably what’s going to happen. This is the things that I’ve put in place to make sure it doesn’t happen again. This is what we probably should do to move forward to recover, so you still are successful. I’m going to just be very honest with you. This is what happened and let’s keep going and it won’t happen again. And two things. One is, they know that they don’t have to search and figure out what happened because you’re gonna come to them. And two, they know that you’re not going to do it again, that you got them and that you’re looking out for them. You’re looking out for their welfare, their budget, their whatever. You’re in it to win it with them, not the other way around. Right? Or you’re not just hiding in an office somewhere.

Steve Comstock:           So it was totally cultural, again, we’re probably going to get to this, but you know one of my favorite sayings is technology without culture is just technology. And you got to break that barrier where you’re not just looked at as the technologist you’re looked at as a critical partner in the success of whoever, HR, finance, your GM of sales, your GM of entertainment, whoever. They know that if they pick up the phone and they’re having a crap day, they can bark at you and you will help them fix their problem and you are in it with them and side by side, arm and arm. And if got to take an arrow for them so they can be more successful, you take that arrow. That’s the way I’ve always operated and it seems to be the way we have to operate moving forward if you’re going to be in that circle.

Tim Crawford:               It seems that from what you talk about in the stories that you tell, part of this is not just taking that arrogant approach of, hey, we got this, we got this, we got this, but when it’s time adding a little humility into it and being able to fall on your sword and say, “Look, you know what? We’re all in this together. Yes, this is on me this time, but let’s figure out how we can move forward.” And that seems to be a cultural shift that’s very different than the past IT where there was no room for making mistakes, which I find kind of ironic considering we tout that we want to be change agents, but at the same time we want to invoke this level of experimentation,

Steve Comstock:           Right.

Tim Crawford:               Curious to your thoughts on that.

Steve Comstock:           Well, I think you have to be open to that. I mean, failure’s not an option. You do not want to fail, but you’re going to fail. And the character of a person is how they respond to adversity. So that’s just kind of run with that for a minute. The character of a person also is how they respond to failure, right? Do they acknowledge the failure? Do they look at that failure? Do they learn from that failure and know that the reality of that situation is this and the next time this happens, this is how we are going to do it. One thing that was really interesting, Tim, as I was going through this is at first I took a lot of fricking arrows and a lot of my business partners were more than happy to put me under the bus just to kind of deflect, not responsibility, but maybe the ire of whoever was angry.

Steve Comstock:           But what I’ve found is as we matured together, I was no longer standing alone. And that was big, right? Because again, you give that sort of humility of, “Hey, you’re going to fail. We know we’re going to fail, right? And we know where the failure points are. And so we gonna do everything we can to protect it, but we know that there’s a certain place of failure. If there is a failure and we did everything possible, then that means that we didn’t know that was a problem or that was an area of failure. Right? Because if we did, we would have done something about it. Right? And if we can’t, we would have said something like …” One of the things, we’re talking about streaming is one of the things I learned was that we kept trying to predict we were advancing television and broadcast into the Internet with streaming, live streaming, direct to consumer, all this good stuff.

Steve Comstock:           Launching things like Star Trek Discovery and we didn’t really know. Right? And so for longest time was we would do these things, it would be a conflict, well, we’re going to get this many people this much stuff, blah, blah, blah, blah. And so we always just took kind of whatever data points we could and build toward it. The pivot was, we said, “You know what? Let’s find out where we fail and when we fail. And then keep pushing, keep testing, keep pushing, keep testing so that I know if you hit this level, you know it’s going to be sketchy, but we have a plan to move back down and get it running. Because at this level, we broke the Internet and we should be doing anything possible to get it back together. But high five and a little bit too, because if for breaking the Internet that means we’re crushing it from a business value perspective that it’s so popular that we need to do more shows like that.” But anyway, I interrupted you.

Tim Crawford:               No, not at all. You’re the guest. I’m just the host. As part of this, I think success is exciting, but success is also very scary too.

Steve Comstock:           Well, you don’t learn anything from success. I mean that’s kind of a weird thing to say, but if you do it right, every time, and trust me. There’s so many people out there that will never admit to failure. I mean how many conferences have we been to where it’s a virtual happy hour of all our success and look how great we are and we never talk about the failures. The failures are where you learn. The failures are where you mature, you grow, you innovate, you pivot. If you never fail, then you’re not growing. And I read an article the other day, or maybe I should be really transparent. I read the title of the article. I didn’t actually read the article. But the title was, If You’re Not Afraid of Losing Your Job Because a Failure, You’re Not Pushing It as Far as You Should.

Steve Comstock:           Something like that. Right? And it was really provocative to be going as a CIO in our roles today, we should be pushing the edge because if we’re not pushing the edge of it, let me say, adds business value, help you move your business forward. You’re not doing your job. We should be pushing things and the most stable, reliable, secure way to help our business get a competitive advantage in whatever market we’re in. And that could be utilizing technology or utilizing technology to build better workflows or optimizing the employee experience or whatever. We should always be looking to push that. And to your question of failure, when you’re pushing that the chances of failure are high, they’re actually very high. Right. And if you’re not doing that, what’s your role? Well, Here’s another cable. Thanks. Here’s another network cable. Thanks. Because they’re not adding value.

Steve Comstock:           That’s because your business partners, the people who were at the top, they’re looking to see how they can move our business forward. And if you’re not there with them going, “Hey, we’re going to take this chance, this is going to push it. But I know it’s a very calculated move. It’s a very educated move but there’s risk, but we’re going to go for it because if we don’t, someone else is and we’re going to get left behind.”

Tim Crawford:               Right. In a lot of ways, companies don’t really improv by making incremental improvements. They have to take those big bets and those big bets do come with risk. But like you said, it’s how you manage the risk. It’s how you respond to the risk, how you prepare for the risk, that really kind of thing defines how you are set up for success and being able to take on those big bets.

Steve Comstock:           Yeah. You know what? I was just ripping on it. I think it defines who you are as a CIO too, and how you’re going to lead, because you’re going the team the way you look at it or the way you make those bets, right? And your team is going to respond or your partners are going to respond to how you do that leadership. I’m going to venture a guess. It’s also going to define where you work, right? I personally, am probably not the best person for a very old school bank. Right? That doesn’t want to take a lot of bets. Unless we’re doing a huge digital transformation, then I’m the perfect guy for them because we’re going to go make a big, huge change, big ideas, or we’re going to try to really capture a market. Right?

Steve Comstock:           So I think it really defines kind of who you are and what your brand is. If you’re afraid to make a change or if you’re afraid to make a bet or fray to get enthusiastic about something, I don’t know. You’re just not me. That’s who I am. I am willing to take a bet. I’m willing to take a chance. And you know what? That’s what makes the job fun. And back to your original question, I think that’s how it’s pivoted too, is we’re allowed to take those chances where before we weren’t.

Tim Crawford:               Yeah, I think that’s a huge difference between the traditional CIO and the transformational CIO is I have a list of attributes or traits that I’ve developed as part of this model and the traditional CIO tends to be very risk averse, and the transformational CIO is much smarter about how to take on risk, but is less conservative and far more aggressive and being able to shift the business. Which kind of leads me into a shift in our conversation a little bit where I want to bring the conversation into technology and talk about some of the emerging technologies that come into these big bets. Things like AI and cloud and edge and IoT. Where are you finding that these are really kind of advantageous for you? Or are there some that kind of scare you a bit?

Steve Comstock:           Yeah, and then some that are more mythical. You put the Easter Bunny, Santa Claus, and the blockchain, they’re all kind of the same, right? I mean, God granted, there’s going to be a huge mark for blockchain sometime, but I don’t know when. Some of these technologies, I think that used to be emerging and you used the word emerging and then you said cloud, which I find interesting because cloud is kind of table stakes at this point. If you’re not moving into cloud, you are probably already four or five years behind, in my opinion, because it’s really the model of how you can culturally change your organization to be more agile, to move faster, to, to scale quicker, to scale back.

Steve Comstock:           Because one of the things about odd that I thought was really interesting, and I’m a huge cloud advocate, so anybody out there who’s a data center person, you won’t like me, but the thing about data centers, etc., that were always a challenge was, it was a fixed cost. So if, depending on your business model and the business model we have, our revenue is variable based on seasonality, right? Yeah. Football season, you have the Grammy’s, you have the Superbowl every three years, you have premieres, you have new show launches, right? So up, down, up, down, scale, shopping season, right?

Steve Comstock:           So your revenue’s variable, but your data center cost is fixed always. And that’s the challenge is when you have these really big events, you gotta go up and down, et cetera. So the thing about cloud, I think is really interesting is you can go and kind of ride the wave. The other thing I think about cloud that’s really fascinating to me and it’ll tie into AI and ML, is I to have a data science team and that we really wanted to pivot quickly and AI and ml two, three years ago, and if you’re listening to this in 2025, this was a recorded much earlier than this, but it was early, right?

Steve Comstock:           And so technology’s changing. Tensor flow is kind of changing. People want to make the models quickly. We want to do big datasets and procure big datasets. Couldn’t keep up. And my data scientists were looking at me going, “What are you going to do?” So we ended up moving to a big cloud provider who had just spectacular large data processing capabilities with really good AIML. And the amount of innovation that could start popping out of that group was just stellar. And if it was slow, it wasn’t because of technology, it was because they couldn’t keep up with the requirements. But I think really, Tim, if you dive into it though, one of the fallacies, I think the CIO fallacies that we have is we’re always looking at emerging technologies, right? It’s like, what’s that new big emergent technology, et cetera? AI, IoT, blah, blah, blah.

Steve Comstock:           I had this epiphany just recently, like within the last six months, is sometimes you miss the business opportunity or the business value in the most unexpected places. We as humans tend to block it and categorize things, right? We stereotype stuff, right? So you look at something that you go, “That is a cabinet and that’s always going to be a cabinet. The only thing that cabinet’s good for is storing documents.” Well, maybe not. What if you put a tabletop? Now it’s an end table. And then what if you do the blah? It could be … put a planner on top of it. Now it’s a guard. I just noticed this just again within the last six months. I think we miss some of the areas that are really starting to get disruptive that are becoming value ads.

Steve Comstock:           I came across a company in the UCAS space and I probably just by saying UCAS, put most of your audience to sleep, right? Because it’s so boring. It’s just not exciting. You’re getting rid of a phone now it’s like, I’d rather write a presentation than do UCAS, but I came across this company that integrated in their platform, super simple. You can click on it with LinkedIn. And I was like, okay, that’s kind of interesting. But what else? Oh, Google or Office 365 I’m like, “Oh, that’s kinda cool.” So now here’s the hidden value. Right now my phone system that has no value, when my salesperson calls out to you, if it’s connected to the LinkedIn, they could see who your contacts and go, “Hey Tim, you know Steve, Steve and I are friends. We’ve gone along way, blah, blah, blah, blah. Hey, would you take this call?”

Steve Comstock:           Or if they’re already connected with you and they have emails, they can say, “Oh Tim just sent me an email that said WTF, and he’s calling me right now. I better read this email before I answer this phone call because I bet it’s about this” Or I didn’t share a doc or had a meeting. But okay, that’s kinda cool.” Right? But then you add in like a Salesforce integration where it auto logs phone calls because sales people, you love them. Their job is not to be document managers. Their job is to build relationships, have conversations and they’re horrible about logging calls. But if you could auto log a call or notice that, hey, we’ve called Tim 16 times this last week, maybe we should give Tim a break and call on Steve and have a whole that Salesforce integration and be able to take notes right on, stay in that phone system, kind of makes the phone that you would traditionally look at a phone and go, “It’s just phone. Who cares? It’s just a phone, right?”

Steve Comstock:           And then integrate like service now. Now here’s, I’ll tie it together, Tim, watch this. You integrate that in with natural language processing and AI. You and I can have a conversation and what we do when like we’re having a business conversation, right? You’re trying to pay attention. You got a notepad or your computer, you’re typing notes and you’re half listening to what’s going on, but you’re trying to take notes. I had a natural language processing. You and I can have a conversation to go, “Hey Tim, we should make an action item of this and do this” or just kind of rip on it. The system itself will record all that in real-time and give you a summary with all your action items and then you can go back and look at it and go, oh, that’s what we were doing.

Steve Comstock:           And what that does is opens us up as humans to go, “Let’s have a real conversation. Now, I don’t have to multitask. Let me just focus on you.” And then you take that, you add it into things like a support center where you can do sentiment analysis or things going wrong. You open it up with sales going as a marketing message, right? As people are objecting to things in the marketing message that marketing people can look at it and then you can tie all this data back into your business and go, “If I’m a subscription business and I’ve had so many bad sentiments and so many good sentiments, how can I tie it back to a potential subscription loss or a turn rate for the people who are calling in? Maybe it’s a horrible show or maybe the price is too high, or maybe the streaming service doesn’t work so good, come see, right?” Or whatever.

Steve Comstock:           You can tie that back and that’s hidden value that if you just looked at the phone, said, “That’s a phone” you would have never seen that value and you would have never contributed back to revenue and the consumer experience as well as your employees experience.

Tim Crawford:               But I think that’s a piece taking this full circle back to where we started this conversation, it comes full circle back to it’s the changing way that the CIO works. Instead of just being that power cord distributor. You’re now thinking about the customer journey. You’re thinking about the employee journey, you’re thinking about how these come together. You’re thinking about, I’ve got this myriad of different tools and you and I were in a different conversation recently where there was some conversation around macro solutions versus micro solutions and how do you start to bring these together to integrate, to find that value? And I think what you just said was so eloquent and so incredibly important, but I think it also exemplifies this shift in thinking around who the CIO is. It’s less about kind of in the weeds and in the nuts and bolts and speeds and feeds, but thinking about how you changed the employee journey and the experience that they have as well as the customer journey and the experience that the customer has.

Steve Comstock:           Absolutely. And the thing about it Tim, too, is traditionally we always looked at budget as our budget. Like okay, I got budget to go buy for WiFi access points and blah, blah, blah. Right? That’s not it anymore. It’s the company’s budget. How can we help our partners be more efficient and find ways to help them be more successful? And again, you got to build that trust, but you do two or three of those and people come to you and go, “You’re my favorite CIO.” And then I’ll say, “But I am the only CIO here.” And like, go, “Yeah, that’s why you’re my favorite. So it’s kind of like, single child syndrome. But you’re right. I mean, that’s absolutely right. And I think that’s the journey is you start looking at that. And I think so important because that’s the value that we can add. Right?

Tim Crawford:               Yeah.

Steve Comstock:           I said, this a couple of times, we’re so talented as a discipline. I mean who else can look at budget, who else can look at workflow processes, who else can look at technology, who else has the whole view of the company and all the interaction points? And if you’re just doling out cables, you’re missing a very exciting thing. And it’s like you get back to your point, the macro environment of “Oh, how does this all work together? And then all the little micro pieces that feed that macro. It’s a beautiful thing and I think some people are just so focused on just having cables kind of don’t see the beauty that’s in front of them.

Tim Crawford:               Yeah, and I think this is also where history has not served us well to kind of help change that mindset over time. We’ve had this role that has been doling out cables and fixing projectors and connecting people to the Internet and installing applications and we haven’t really stopped and said, “Okay, how do we think about that customer journey, that employee journey? How do we think about our business, how our business makes money, how it spends money?”

Tim Crawford:               As we kind of wrap here on the conversation. Put a bow on this. You’ve talked a lot about what’s exciting you, but if you were to kind of hone in on what excites you most about the CIO role today and where it’s headed, and kind of where technology fits in, if it does in your mind, what would you say?

Steve Comstock:           I think the most exciting thing about it is the CIO role is becoming a business role versus a technology role. Especially as you look at it some of these companies as they mature. Full disclosure, I was at a digital company, we still do digital transformation, but I was in the Valley. But, everyone’s a technologist anymore. And so the differentiation of being a technologist isn’t there. So just the fact that we’re able to start becoming more business partners and business roles, and looking at that component of it is so exciting. It really is super excited because I’m a coder by trade. I can look at code and that’s fun. I can create something new, that’s fun. But really be instrumental in changing someone’s, maybe this is too Highfalutin, but their life and their work experience because we spend so much time at work that you can change how that when they come into work, they feel like they’re getting stuff done, at least from a technology perspective, from a business perspective.

Steve Comstock:           That you’re helping move a business forward and that you can go high five your business partner when you have a great release or when something goes really well or when we crushed numbers or whatever because you were part of that party and we’re part of the game and we’re part of that. We’re part of the family. It’s not just like where that crazy uncle who sits in the corner on the Commodore 64 anymore, right? It’s like we are the crazy uncle who’s right there in the middle of it, partying it saying, “We got to do this, guy. This is going to be awesome. I double dog dare you to jump off that roof because this was going to be cool.”

Steve Comstock:           Right? And that is the fun part because you really becoming business partners. I can’t go as far as we have a P&L or a revenue line and people say, well we should have a revenue line in IT. I really question that because it dilutes from what you should be doing, but at least you can affect other people’s business line and you help them and you just being involved and being brought into some of these things is so much fun. And I think that’s the exciting part is that big transformation.

Steve Comstock:           One last comment, because you see it with a lot of the CEO’s who are transforming themselves into the COO role, right? Which, would have never happened before. That was just not even … We weren’t even considered for something like that. And you see it, you see CIO’s who are moving into the CEO roles, right? Of companies that maybe aren’t tech companies and you’re like, “Wow, how did that happen? That is so cool.” And that, I think is a big thing, and that just supports my thought is we’re becoming business people who have strong discipline and technology, but that’s exciting to me, Tim, to be honest.

Tim Crawford:               That’s great. That’s great. We’re going to have to leave it right there, but Steve, thanks so much for taking the time to join the program and hopefully I can have you back again for a continued conversation and maybe unpack some of these thoughts a little further.

Steve Comstock:           Absolutely. I’m just doing for once, thing, just the virtual mic drop. That was a lot of fun, Tim. Let’s do that again and I think this is a super exciting thing you’re doing here, so keep it up.

Tim Crawford:               Great. Thanks, Steve.

Tim Crawford:   For more information on the CIO In The Know podcast series, visit us online at, or you can find us on iTunes, Google Play, Stitcher, Spotify, and

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