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The CRO Spotlight Podcast examines the CRO role from both sides — the companies that hire them and the leaders who take the seat. Host Warren Zenna, founder of CRO Collective and author of “What Chief Revenue Officers Actually Do,” brings diagnostic frameworks and pattern recognition from working both sides of the equation to every conversation.
Rob Wilk Podcast Transcript
Warren Zenna: Hey, everybody, welcome to this episode of the CRO Spotlight Podcast. This is Warren Zenna. I'm the founder of the CRO Collective and exciting weeks we've had with some great events. I want a big shout-out to the partners over at Fullcast who've been helping us manage these events and they're terrific people, great technologies. And we have another couple of events coming up. In fact, we have Boston on October 27th, and then Austin, Texas, on October 28th, which is my birthday. And if you happen to be a CRO in either the Boston or Boston Metro or in the Austin or Austin Metro, definitely go to the website, thecrocollective.com, to the Events section and you'll see all the links to register for those events. They're great, and I suggest you come. Also, we are kicking off the next iteration of the CRO Accelerator course next week. We have a great bunch of CROs and aspiring CROs being in this course. Again, like I mentioned, this course is incredible. I mean, I know I'm being a bit biased here, but you know, I built this thing about six years ago and it's evolved and we're at a point now where this is the operating system for a chief revenue officer, whether you have the job or whether you're looking to be in the job. This is just such a great program and if you're interested in it, you can just also go to thecrocollective.com. There's a courses section. You can apply to it and we'll get back to you. Anyway, today we have a great guest. I had a meeting with an amazing executive, Rob Wilk, who is the chief revenue officer of Yahoo. Amazing, right? So Yahoo is such an iconic brand and this guy, Rob, you know, he really has had an amazing career. You know, he was with Foursquare and Snap and it's really quite cool and he came from the same background as me. But anyway, you know, sometimes I have guests where we're just immediately like-minded in so many ways. This is a really insightful conversation. He's a really super person. You can tell he's just an exceptional leader and I really recommend you listen to this 'cause this conversation was great in so many ways. So thanks for tuning in. Again, you know, make sure you give us some ratings, share the podcast with people. We're getting an incredible amount of traction here. We get so many people to listen to this podcast. I get probably four or five LinkedIn notes a week saying, "Hey, I love this episode," and stuff. So I really appreciate it. Everyone that listens is really helpful, so thank you for doing so and thanks for the support and enjoy the show. So really great for being here. Thanks so much. So you've got a really awesome career and you worked at some of the brands that were really close to me when I was growing up. You know, I think of Foursquare, my God, I was, like, addicted to that thing. And you know, I had the Snap Glasses when they first came out. Remember those things? So you know, I'd love to get a little bit of your journey because the thread here, as you know, is we're gonna talk about this chief revenue officer role, and you have some really important mandates under your belt you've had. It'd be great to get some perspective on how we align on that. I don't know how much you've studied what we're up to here, but you know, it's an interesting role, you know? And people who've had the role like you for such a long time, it's really great to get that perspective on it. So if you don't mind, just a little bit, just a quick background on how you ended up here kind of thing.
Rob Wilk: Yeah, I mean, you know, it's a very long story. I'll try to keep...
Warren Zenna: Great. It's okay. We got time. It's all good. Yep.
Rob Wilk: So the short version is, I actually started on the buy side. So it's not even updated. It's 1995, you know, it goes back a while. But...
Warren Zenna: Same. Yep.
Rob Wilk: side of a very well-known Madison Avenue ad agency called Young & Rubicam.
Warren Zenna: I remember very well.
Rob Wilk: Became Y&R, now it... with VMLY&R, now it's something else. And just by accident, like I was a teacher. I wanted to do something different. I called my roommate from college who worked at Y&R and said, "Can you get me an interview?" And he did, and I was an assistant media buyer. I knew absolutely nothing about advertising or media. I love to tell people it was a suit and tie place in 1995.
Warren Zenna: That? Remember?
Rob Wilk: And I wore the same suit every day because I only had one.
Warren Zenna: Amazing.
Rob Wilk: That's how it was. I just changed my shirt. I did that for a few years and I started to learn the business, but part of my job was to meet with sales reps. This is pre-internet, so the sales reps I met with were mostly magazine and newspaper. And they were terrible. I thought they were terrible. I'm not exaggerating. So every time we'd leave, I'd say to my boss at the time, I'm like, "Why are these folks so bad at this? Like, it's just amazing to me." Fast forward a few years, she finally said, "Rob, I hope you don't mind me saying this, but I think you're on the wrong side of the table. Like, I know that you're a good buyer. We love having you. I think you'd be better off in sales." Which is like the best thing that anyone's ever told me because I, through a friend of a friend, got an interview at Ziff Davis Publishing. That's, you know, PC Magazine and all the big magazines.
Warren Zenna: Worked with those guys very closely, all those dudes.
Rob Wilk: Yeah. So there's a gentleman, I love to call him out. His name is Todd Anderman. He was my first like sales leader, first mentor. In those days, an associate publisher was essentially a CRO, right? 'Cause the publisher had a lot more editorial, you know, things that they needed to do. The AP was really like the early days of what you and I now call CRO. Taught me everything there is to know about selling. Just a great human being. I'm still friends. I just had lunch with him last week. And I traveled with him on a few different jobs. But then, you know, the internet, he and I went to do an internet startup in '99. Then I really fell in love with search and that's really where the trajectory really changed. I was selling what people will know as, like, display advertising, but there was a company called GoTo.com.
Warren Zenna: I remember GoTo.
Rob Wilk: That then became Overture.
Warren Zenna: That's right.
Rob Wilk: Hand to God, I cold called the woman who was leading the sales team and said: "You don't know me, but you're gonna love having me on your team." Got an interview, got the job. There were six of us selling this thing called search advertising in 2002. I fell in love, and the reason I fell in love is the model. The media was always negotiating. This was the first time where the media was not negotiated, it was an auction. So I didn't have to, you know, argue with you about, "I think it's worth X," but you think it's worth Y. When a seller and a buyer take price negotiation out of the equation, guess what happens? You actually have a great conversation about what the buyer is trying to do and how the seller can help. I absolutely fell in love. Overture was acquired by a very large internet company called Yahoo. That happened in 2004. So I had other, more senior roles, started to, you know, grow my team and, you know, become a manager and all that. But really the step function change was when I left Foursquare to join Microsoft, and I was there for eight years and eventually led their ads business, which is, you know, $20 billion a year. It's not small. Two and a half years ago, I rejoined Yahoo because I have a relationship with Jim Lanzone, who's the CEO of Yahoo. We can get into all that and being owned by an equity firm, Apollo, all that good stuff. But Microsoft and Yahoo have a longstanding search partnership. So when Apollo acquired Yahoo and put Jim in as the CEO, Jim called me and said: "Hey, I wanna talk to you about our partnership." There's billions of dollars involved in this partnership.
Warren Zenna: For sure.
Rob Wilk: And it wasn't going well. And this is why I love Jim Lanzone. He was like: "I hear it's not going well. Is that true?" And I was like: "Yeah, it's true." And he said: "Do you wanna fix it?" And I was like: "More than you could imagine." And we did. So through that relationship, years later, next thing I know, he's calling me and he's like: "Hey, I think I have an opportunity for you that we should talk about." So that's the shortest version of...
Warren Zenna: That's great. That's great. So I'd be curious to know. It's really, really awesome. I want to dig into this a bit. What was broken about that partnership, and what did you fix, and how did you fix it?
Rob Wilk: Yeah. So first of all, the partnership is going on 15 years now. So you can imagine the different changes between the two companies. If you think about Microsoft 15 years ago, it is not the Microsoft of today.
Warren Zenna: At all, no.
Rob Wilk: And you can say the same thing about Yahoo in a lot of different ways, right? So honestly, a big part of the friction was there were people on both sides that had worked together for years and didn't particularly like each other. So there was a lot of personal friction, people that had just been on the same deal for too long and needed to like to do something differently. How we engaged with each other, we completely reinvented that. And even so I like to think big things, and I'll give you a really small one that actually made a difference. Every time Microsoft would present to Yahoo, all of the materials that Microsoft presented were in the Microsoft look and feel, Microsoft logos everywhere, Microsoft templates. And I just said, "They are a partner. Why don't you put both logos on every slide? Why don't you have a different look and feel that feels a little bit more like you're reaching out to Yahoo versus Microsoft trying to stomp on you?" And that's really small...
Warren Zenna: No, it's not, but it makes it... I could totally get your point. It sort of communicates something that doesn't foster partnership. And...
Rob Wilk: It's, you know, Microsoft is, you know, obviously it's huge. You know, this is pre-trillion dollar valuation, by the way, but they were still, like, huge, and I think they always viewed Yahoo as less than, and they made it very clear that they viewed it that way. So how do you think people react to that? They don't like it. It's like, it's not complicated.
Warren Zenna: Yep.
Rob Wilk: So I say this all the time, like I wouldn't look you in the eye and say that we fixed everything. I think we made some significant improvements and the teams are much more collaborative now. They share more openly. There was always this notion of like, "Okay, tell Yahoo these three things, but don't tell them those." And Yahoo had the same version of like, "Okay, don't tell Microsoft these things. Tell them those things." And listen, we're still partners today and things are significantly better. That's the way I'll leave it.
Warren Zenna: I got it. That's great. I like it. So, you know, what you just explained is, you know, it's not like nuts and bolts and data and connectors and back-end stuff, it's people stuff. It's like how people relate to each other and how they work together and how they foster an understanding to build a business. And the CRO role is pretty much mostly that, you know? And I think that a lot of people that get these big CRO roles don't realize how much of it is politicking and people coalition building, and you have so many stakeholders and, you know, you think you're going in to build revenue, and in fact, what you're trying to do is just get everybody working together around one goal. And, you know, if that skill set is not in your back pocket, you're probably not gonna be good at this job. And we tell this to people all the time, like, "I know you ran a sales organization and you built a good pipeline, but you know, this is not the same thing at all." So I'm curious to know what your thoughts are on that and how people make that jump, 'cause we see a lot of times they don't, and I wanna get a lot into this 'cause this is how we kind of help fix that problem. I'd be curious to know your thoughts are on that.
Rob Wilk: I mean, I am not sure I could have articulated it better than you just did. I mean, it felt like you were inside my brain when you just said that. Here's my observation, and then we'll talk about it, okay?
Warren Zenna: Sure.
Rob Wilk: You ever see those salespeople like, you know, individual contributors, crushes targets all the time, never in the office, always out with their clients, and everybody sort of tiptoes around these types of folks because they're just killers, right? And they'll have attitudes that say things like, "Yeah, I don't care how, just get it done. And if you can't, I'm gonna go complain to someone else until they get it done." And what I have noticed is those folks who want to take the next step like a frontline manager or a manager of managers, they fail 90% of the time. And the reason is because I think you have to be sincerely interested in the machinery to run it at a large scale. If you have the attitude of like, I don't care how something goes from A to B as long as it does, that's a great recipe for a frontline seller. It will not work as you move up the chain. So obviously, you know, this is your whole, this is what you do. I talk to a lot of people early in my career, mid-career, and some of the feedback that I get is that people are surprised at my level of interest in things like ad operations, as an example. I don't wanna do that job, but I certainly wanna understand it. And the leader of my own ad ops org, I talk to her probably more than any of my other directors. And I think there's like a misconception out there that salespeople don't, or sales leaders don't care about those things. And I would argue salespeople don't care, sales leaders have to.
Warren Zenna: Yep. Yeah, they do. I mean, the good ones do. I mean, the ones that succeed, I would say what you're describing and, you know, it doesn't surprise me how you ended up where you're at is how I would articulate a similar thing would be that you sort of have to be more of a systems thinker than a functional thinker, you know? And some people aren't systems thinkers, you know. They don't look at... So I was in the restaurant business before I got into advertising, you know, and I loved it because a restaurant is a little system, you know. So if a customer walks in the door, you know, there's all sorts of systems that impact that experience, then they work together and coordinate it, and the people that run restaurants really well understand the system. And they really get like how, you know, there's this back of the house that's producing the product, and there's a way in which that product, when it reaches the table, is part of the experience, and the back of the house has to understand the front of the house to do that. And if they don't, honestly, it's like it literally doesn't work. And similarly, you know, the front of the house has to understand how the back of the house works. And, you know, the people that run restaurants really well are system builders. They just understand, like, components of how a whole thing works. And a CRO is the same thing. You're running a big, huge restaurant organization ultimately, you know, and you have like the delivery of the food items you buy, and you have the garbage guy that picks up the garbage, and you have someone that cleans the floor, and you have the guy that brings in the linens, and you have someone that cleans everything. And you don't realize how complicated it all is and how when it all works together, you know, a customer walks in and goes, "That was amazing. It was amazing." And it's like, yeah, no, but it's not just a simple matter of you just walking in and sitting down and eating. It's like you have no idea how much goes into you having that experience, you know. I had this really good argument with one guy who ran a restaurant. It's a funny story. So I was a real systems thinker type, you know, and I was looking at everything, and I was running the bar at the time. And he gave me the opportunity to manage the place. I was like, "Fine." Started looking at all the ordering, and I saw, like, you know, the coffee that he was buying was this garbage. It was like this real low-end coffee, came in like these crappy bags, and he bought it in these big, huge things, and it was just bad. You know, I drank the coffee. So I ordered this really good coffee, you know, and he came to me screaming like, "What are you doing? You just destroyed our coffee margin." I said... I could think about it. I said, "What's the last thing people have before they leave the restaurant? They have a cup of coffee." You want them to leave like that, you should top it off with the best thing, not the worst thing. Like, why would you plop a crap of shit on top of a great experience because you want to save a dollar? It makes no sense. And he couldn't understand this, you know? And I realized, you know, this guy's place went out of business in about a year. But, you know, you have to think that way. And the CROs we work with, like you just said, they talk to the rev ops person, and they don't really understand that particular part of the business, but they understand that person and what that person deals with on a day-to-day basis, and how that person interacts with the other people, and you can fix those things 'cause you're thinking that way. And to your point, great sales leaders are already thinking about those things. That's why they tend to be promoted to CROs. So I'm just curious, like, was that consistent with the way you felt you were more singularly capable of running a system? Do you think you're more of a system thinking person, or were you just a great sales leader and you knew how to, like, gather the troops? How does that resonate for you, what I just said?
Rob Wilk: Maybe half and half. Just let me just pause. I love the restaurant story, by the way. And a woman that led ops at Microsoft who was really good at her job, like you have to be good at operations at Microsoft or they will chew you up and spit you out. And she had a saying that I use all the time, and it is like, "Great operations are invisible." So that's exactly what you just...
Warren Zenna: Yeah, it does. You don't see it happening, but it's like magic almost in a...
Rob Wilk: Yeah, it's just, it all works and therefore you don't notice it. It's like flicking the light switch every day you get home. It just turns on. You don't think about electricity all day. You just expect it.
Warren Zenna: You don't think about the plumbing till the toilet's clogged. All of a sudden you think about plumbing, you know.
Rob Wilk: So I like this notion of like great ops is invisible to the org, but again, not invisible to me. I like to know how everything works because I'm looking for ways to make it better and more efficient, and most importantly, as friction-free as possible for somebody to buy from us. We can go back to this if you want to, but we were notoriously difficult to buy from. And people did it because we were the head honcho for the, you know, late '90s to 2010.
Warren Zenna: Yep.
Rob Wilk: And guess what happened? Other companies with scale came in and made it ungodly easy to buy from, and Yahoo saw that, you know, decline. So again, that's just a big part of it for me. I was thinking about you yesterday. I'm like, "Oh, I have this podcast and I love talking about this stuff in case it's not obvious to..."
Warren Zenna: Yeah, me too. Me.
Rob Wilk: So I'm thinking in my head like, you know, what are some of the things I wanna talk about? And one thing kept coming to my mind, which is this: I wanted to be... I didn't know CRO, but I wanted to lead a team forever. And the reason why is not what you think. It is because I have been blessed with some of the best leaders ever. Like I'm super lucky, but I have also had terrible ones, and I think I learned more from the terrible ones than maybe I even did from the good ones. And I had multiple scenarios where I was a junior seller watching somebody else do something, say something, and I would constantly find myself going, "I would never do that," or, "I would never say that. And if I ever get the chance someday to be standing where they're standing, I will do it differently." I had literal dreams and fantasies of these moments. And one of my favorite examples is, this is a 20-year-old example, but I was working at a company that was not doing well. You didn't have to be a genius to know things were not going well. Head of sales or CRO, whatever you wanna call it, gets up there. "I got some great news. We're killing it on this. We're killing it on that. I'm so excited. Everything is amazing. Get out there and crush it." And then everyone leaves. All the sellers get together instantly and say, "What'd you think of that?" Right? This is again like when everyone can just get on a Zoom call, right? And every single one of us was like, "What was that?" That was a complete fabrication. And I believe that there are people who think you can't tell the troops what's going on because they'll freak out and they'll leave and there'll be a mutiny. My response is always, they are adult humans. Yeah, they're junior sellers, but some of them are married and they have parents and they live... Like, if you don't tell them the reality, A, they see right through it, and B, you've lost them. So when you ask me like, you know, why did I get here? It was never an aspiration for the title. It was an aspiration to be in a position where I could do what I thought was better, more humanly, if that's the word.
Warren Zenna: It does, it makes sense. Sure.
Rob Wilk: But not this like corporate rah-rah that you think you're fooling them, and the only person you're fooling is yourself because everyone sees right through it.
Warren Zenna: Hundred percent. Everyone already knows what's going on.
Rob Wilk: Yeah.
Warren Zenna: Right? So you go out, you make these pronouncements to everybody to put on some leadership, you know, persona, and if it's not handled properly, which, you know, you're speaking to the key thing, which is the EQ part of the job, which is the key thing, frankly. When we see the CROs succeed the most, they have, obviously they have business acumen and financial acumen and all that stuff. What they really have is they have incredible EQ. You know, and they understand all these things, and they operate this way. Because what we've kind of concluded, it's really funny, the whole evolution of this whole thing we did for the last seven years is, it's a revenue leadership position and there's all these obvious things attached to it which you know, which is growing the business and getting more customers and building revenue and getting more of it done, all the other things like that. But as we chipped away and chipped away, I want to talk about the other side of it, which is the company itself, but on the CRO leadership side, what really, I said in the beginning of this thing, what it really is, is these are people whose job it is to actually, their currency, the currency of a CRO is one thing, it's trust. And if you can't build that and keep it, you're probably not gonna do well because ultimately the trust scales up to the board or the CEO, and when they lose trust in you, you have to work really hard to get it back, and if you never do, they're already looking for your replacement. And we see this all the time. And it comes from, honestly, it doesn't come from missing your number. It doesn't. Actually, the reason why they fire you for missing your number is 'cause they don't trust that you can do something about it. It's not that you didn't hit your number, it's that they don't think you're gonna be able to do anything about it. If you're really competent and you do well and you miss your number, they understand we're gonna miss our numbers sometimes. But we trust this person. He's really smart and competent, and he's a great leader, and his plan is good, and we're gonna give him a little latitude because we trust him. And if you don't understand that, you're gonna lose... This is why we see CROs lose their job in about 18 months, because they lose trust. Actually, in about six months, the trust is gone most of the time. And what's happening is the organization is sort of in this, we don't trust this person, and the CRO is like, "I can feel they don't trust me." But like you said, they don't discuss it. There's no framework to work it out. They just sort of work in parallel universes until, and there's enough anxiety that they just go, "Just get rid of this person already." And, you know, it's like this sort of, like you said, this sort of ignorance that takes place, and I think the EQ part is having a framework and an SLA that allows for you in leadership to have conversations like this exactly when things happen so that trust can be reestablished. And if you don't have those things in place, I don't care what a good operator you are. Without that trust, you're done. It's finished. 'Cause there's too much at stake. They want you to 10X the business, and if they don't think you can, they're gonna get rid of you. There's no way, you know? So we just see how often the problem is, and this is an interesting thing I want to get into with you, 'cause it was a great story, by the way, is the sales leaders come from a much more metrics-driven environment. Like, if they can keep closing deals, they're gonna get patted on the back because they're the functional component of their business, the section that they run is to drive more logo acquisition. If they can keep doing that, the company will tolerate quite a bit from you because you're delivering enough manufactured goods to the organization to continue to chew on. And then, you know, they'll blame Sharon on CS, but you're doing your part in the orchestration, right? You're a great horn player. The violin section sucks. Just keep playing good horns, we'll just replace the violin section, right? But when you're a CRO, you conduct the whole thing. The horn player's your fault, right? So it's not the same. So when we see people come into this job as great sales leaders, and they don't put down the French horn and learn how to play the violin, they can't horn their way through that job. They have to learn how to actually orchestrate, and if you can't make that jump, you're not gonna succeed in the job. So I'm just curious, like, how do you make that leap? What's the way that... Do you know how to do that? Or is it, like, something you learn? Like, what are some mistakes you saw you made where you saw, oh my God, and now I'm not gonna do that again, that sort of stuff.
Rob Wilk: Yeah. I mean, so I have a... I have a derivative of your trust principle.
Warren Zenna: Yeah?
Rob Wilk: It is this. So Yahoo is owned by Apollo, a private equity firm. Obviously I had to meet some of those folks before I joined.
Warren Zenna: Of course. Sure.
Rob Wilk: and first board meeting, they were like, "Rob, you're on the hot seat. What's the plan?" Right? And they came after me pretty hard, and we got to the point where we were just ping-ponging back and forth. Now it turned out Apollo's view of that was like, "He's our guy. That went great." My perception at the moment was like, "Oh God, I don't know how this is going." It just felt like one after the other. And it was, they wanna have confidence.
Warren Zenna: Yep, that's right. They're testing your... they're testing your resolve to see if you can handle being in the hot seat, and obviously they liked what they saw. You walked out feeling you got the shit kicked out of you, but they were like, "That was great."
Rob Wilk: Oh, they were fine.
Warren Zenna: That's awesome. Yeah.
Rob Wilk: What I think breaks that, so that my derivative of that notion of trust is people that don't do what they say they're going to do. So we're always gonna negotiate on, you know, Jim Lanzone and our CEO, he's always gonna want me to bring in more revenue. I could bring in a trillion dollars. He's like: "Where's a trillion in what?" Right? And our PE firm is gonna say the same thing, and that is what they should be doing. So I focus very much on like, I understand that there are expectations, but let me tell you what I think we're gonna do. And those numbers may not be the same, but I am very consistent about this is what I think we can do, and sometimes I'm stretching it 'cause I see a lot of goodness in my pipeline. Or another, we had one quarter where I was like: "Hey, I wanna let you know right away we have a problem and here it is." So my version of trust is, is Rob going to do what he says or is Rob going to make sure that his team does what he says they're gonna do? And if they're not, is he open about it and upfront about it? I don't hide my warts, and I'm very clear about my wins. When I... I shouldn't say my, our wins, the team's wins. And over time that is where that becomes the bedrock of trust. I have seen other folks try to negotiate their way to a better meeting but a worse outcome long term because they decided they're gonna go in really optimistic because they know it'll please the CEO or the board or whoever, and in that meeting they're psyched. A month later when they start looking at actual revenue trends, they're toast. So I try really hard to do that, and if I say we're going to do X, I am either going to achieve X or I am going to give you updates on how we are trending towards X, and if we are not going to hit X, why? So your point around like the navigation of it, I tell people all the time, the CRO is not the VP of sales.
Warren Zenna: No.
Rob Wilk: I would argue that I'm not very good at pitching in a client meeting anymore. My VP of sales, she will crush that. She is so good at that, and she directs and all the frontline sellers in a pitch off, I would lose. But that's not the job anymore.
Warren Zenna: No, it's not, it's not the job anymore. And the thing is we see people who are, like that woman, I don't know what, it doesn't matter who she is, but just use her as a cipher for this particular comment. She's good at this, right? She's a killer. She knows it. She knows she can walk in a room and she can just razzle dazzle everybody. And then she gets a CRO position, and she's nervous as hell because all of a sudden the pressure's on and she's being asked to do a lot of things that she wasn't doing before. And so what ends up happening is she starts dipping herself into deals 'cause she knows she can kill it there, 'cause that's where she's strong, right? And after a while they're going, "What is she doing? She's supposed to be out of this already. Like, move on. Like, get somebody else to do this for you." But, you know, we see the CROs who are really good at that thing keep doing the thing they're good at because they think that's the formula that got them the job, but they need to adapt things now... Like, you gave it up to the point where you're not even good at it anymore. I completely know what you're talking about, believe me, I do. There are a lot of things I was really, really awesome at like 10 years ago that I could probably still do, but there are people that could do it better than me and I don't want to do it anymore.
Rob Wilk: It's like a sport. Like, they practice every day. You know, I'm a retired guy at this point. Like...
Warren Zenna: Exactly. But this is a big failure, and I... This is an interesting notion. So what we're seeing now. You and I have been talking from the perspective of almost an assumed perspective that the CRO is born out of a sales leadership position. And traditionally it has been that way, and for obvious reasons, right? What we're seeing now in the last three or four years is less of that. We're seeing a lot more rev ops people get this job, other operators get this job for the reasons I'm saying is that, you know, and I'll say rev ops specifically because they, as you know 'cause you work with them, rev ops people are by nature, they're very system-driven people. They think about the whole picture. They have to. That's their job, is to connect dots and build intelligence across the streams, right? And they tend to think about a journey to the customer 'cause that's how their metrics work, right? You know, these people aren't encumbered with a functional focus when they get at the job 'cause they're looking at things from a systems perspective from day one, right? And they're not tempted to go run to deals 'cause they never did that in the first place. So we see a lot of salespeople fall back on that a lot. Or what ends up happening is they're managed that way, and that's because the scope of the role is not clear. And this is where I actually implemented this entire thing in the first place, why I started this, is that CROs get hired to run against two clocks. It's funny to have this clock behind me. So there's two clocks. The one clock is the quarter clock, right? Which is the one you're being hammered about every day. How are we doing this quarter? Are we gonna hit the quarter? You know, and quarters are a series of months, which are a series of weeks, which are a series of days, and you can get myopically caught up in that to the point where a quarter is all of a sudden right upon you, you didn't even think about it. But at the same time they're saying, "And retool our business. Make it work stronger, make it more efficient, get better people, you know, expand it." And doing those two things at the same time is really difficult because the amount of time required to retool a business is longer than the window you have to close the numbers that they're looking at you about every day. So we talk a lot to CROs about how they manage that when the job scope is unclear because the organization has sort of a dual purpose, which is we want this person to kill it this month, but we also want this person to build us a new business at the same time. So how do you suggest a CRO manage that, those obvious issues that face them with that job?
Rob Wilk: I mean, once again, it's starting to be unnerving how much you are inside my brain. It's starting to make me weirded out, in a good way. Well, there's two things. I think I'm particularly blessed because in our organization, we have quarterly targets, but they are more a function of the comp plan and more a function of a check-in to see how we're trending. But our numbers are really geared towards a full year. Okay? So I am lucky that Yahoo thinks that way, and I'm certainly lucky that Apollo...
Warren Zenna: So you're in an environment where there's less of that quarterism 'cause of the environment you're in right...
Rob Wilk: No. I mean, yeah, I mean, I guess less yes, but not zero. Like, there's certainly lots of conversations and check-ins...
Warren Zenna: But you're saying it's not as much of a pull as maybe you would see in other places?
Rob Wilk: No. Especially, you know, we are lucky to be privately held. I can imagine, and I have worked at publicly traded companies, you gotta beat the quarter. That's it. And they don't have that balance. We are blessed to have that balance as a private equity-owned company. So, but again, we have a quarterly rhythm with Apollo. I have a quarterly rhythm with Jim, our CEO. And there are questions like, "What happened in March?" Like that... I'm not saying that doesn't...
Warren Zenna: Of course. Yeah.
Rob Wilk: But the ultimate like, you know, do I win or do I not win is the year. And another area where I think people can get tripped up is I use the term "Do I win?" a lot. I play out scenarios for the board and for Jim. "Hey, if this happens and this happens, do I win?" I ask him that all the time. I need to know that information, and it is because I grew up as a salesperson, so if the quota is a million dollars and I do a million and one, I don't have to ask my boss if I win.
Warren Zenna: Right.
Rob Wilk: That's why I like the job. I am fascinated by people who don't have metrics. How do they negotiate a raise or how do they decide that they had a good year? It feels like it's just totally up to the person you work for and hope that they're in a good mood that day.
Warren Zenna: Sort of is, in a way.
Rob Wilk: Yeah, I don't like that. So I like the notion of metrics, but we do... I guess what I'm saying is I'm lucky that I have the right environment where quarterlies are important, but years are the goal. Years are how you win. 'Cause they also understand that there is, you know, hills and...
Warren Zenna: Of course, this is gonna happen, but the year matters. I mean, 'cause I... that's great and you know, congratulations on that 'cause the majority of people don't have that benefit. You know, even though that might be true, the organizations and our clients, the majority of them are myopically focused on quarters, you know, to the point where, you know, CROs are being asked to do monumentally transformative things for the organization, and then from day one they're like, "Okay, by the way, we're really down for this quarter, so let's get on that right away."
Rob Wilk: And that has happened to me. Like, let me be very clear, that has happened to me, and I think it sucks. And the CRO's job is to be articulate about what the downstream impacts will be if you only care about closing the gap in Q3 and you're not thinking about calendar Q4. And I've had those conversations too. "Hey, you want us to go run out with a bunch of discounts? Let me show you how that plays out over the next 12 months. 10 of our clients will be spending half of what they're spending now. So let's not panic here." But I would've never... I would've never said when I was 20 or 30, "Hey, you know what I wanna do when I'm in my mid-50s? I wanna negotiate internally with all my stakeholders. That's what I wanna do." I would've never said that. In fact, 30-year-old Rob would've been like, "That's... I'm... That sounds like my worst nightmare."
Warren Zenna: Hmm. What changed, do you think?
Rob Wilk: My complete acceptance of if you want to have influence, this is what it takes. I wanted, you know, to talk about systems thinking again. You and I have all the same concepts in our head, we just call them different things.
Warren Zenna: Yeah, sure. Of course.
Rob Wilk: You call it systems thinking. I think of myself as an environmentalist. What is the environment that needs to be created so that people can win, can enjoy their jobs, and clients love us? Like what is that environment? And then I give them that, you know, we present that environment and say, "Go succeed." Like that is the way I look at it. So yeah, I have to do a bunch of things that are not particularly pleasant, but I try to think about what you said if you got here, you would do it this way and that sellers would have a certain type of experience. This is part of that.
Warren Zenna: Mm-hmm.
Rob Wilk: There's no job out there, even if you're running your own business, you have your own company. If I asked you, "Give me five things that suck about your job," you could name them off the tip of your tongue. There's no such thing as a magical perfect job where everything is great.
Warren Zenna: There's none.
Rob Wilk: My embracing of the notion of, you know, my Microsoft team was thousands of people. You know, Yahoo's is hundreds of people, but still, like this is a sizable group of people out there that I have some level of, you know, responsibility for their success and responsibility for their work-life quality and success for their happiness. And I take that very, very, very, very, very seriously.
Warren Zenna: Yeah, well you care obviously. You're a caretaker, and I get it, and it's important to you, and it matters to you for the reasons you've already articulated and that's great. I mean, again, that's an EQ, that's an emo- See, there's, we have a number of different types of profiles for people that take jobs like this. Some people, and they're all good reasons, by the way. There's no wrong one, but they just have different success formulas. One is we see a lot of CROs that want this job because they recognize that there's a big financial opportunity there for them. They just make more money, right? If they become a CRO, they'll get some equity and, you know, they're the ones that could bring the company to a next level. They know they can get an earn-out or they can get an exit, and they like that possibility, and they end up making a lot of money, and that motivates them. Some people, honestly, they just want more power. You know? They want to, they're sick and tired of being a piece of a system. They wanna run it, you know? They have a, I wouldn't say it's a negative authority thing, they just wanna be in charge, and it's because they have an ego, and they're competent, and they think that they could probably just run things better, and they'd like to. And then there's people who love people, and they want to provide an environment where people can do great things and succeed, and they know that all the ships get lifted that way. Those are more EQ-driven leaders. We tend to see those are the ones who tend to become, you know, the kind of people that you talk about, right? The one that you look back on your career and there's, like, two or three bosses you had that you just fell in love with. Those are the people like that. They just walk around, they sort of, like, just care about everybody, you know? They take the time, they sit you down, you know? And maybe they'll make a little less money doing so, but the payoff for them is because they've made a difference, and that's what they really wanna do, and they end up doing really well as a result. And I think this job is... I wanna talk to you about this. An interesting part of this conversation is, you know, the human part of the job. Like, you and I are the same age. We grew up in the '90s, and we got these jobs through the time when it was a real, we grew up in a people business, you and I, right? I mean, it was a, man, the '90s and it was, like, in the early 2000s, like, a people business, hands down, you know, working in agencies with all these rooms to people, and it was just people, people, people. And your people skills had to be really good. And now we're behind computers and we're running, you know, Claude and ChatGPT and stuff, and I feel it. It's just different, you know? And I'm curious, like, so what is, for you personally, around the advent of all this stuff? And then I'm really curious what your thoughts are on how AI is impacting the programmatic advertising space, because I know it is. I mean, just so you know too, I have a marketing agency as well, and we do search, so I'm very still in this, right? And we're seeing it. It's insane, right? But I'm just curious now, running a company the size of Yahoo, how are, what's your thought on both the kind of moving away from people first, almost tech first, and how is it also impacting the way people are buying and selling media, and what are some thoughts you're seeing on this right now? I'm really interested in that.
Rob Wilk: Yeah. And as someone who saw success in it when it was people first because I got to wield my most powerful weapon, which is my ability to connect with people.
Warren Zenna: Same thing. That's where I grew up and thrived.
Rob Wilk: Yeah. I went through like a death and then acceptance, like all of the steps, you know, COVID and then, you know, remote work. And I've sort of come full circle now. So I had to mourn the death of what I knew and grew up with, but I have a little bit of renewed energy around this for a few reasons. Number one is, I don't care that we're on video. If you were sitting across from me, and I get the sense that if I was sitting across from you, this is exactly how I act.
Warren Zenna: Same.
Rob Wilk: So there is no, there's no video Rob.
Warren Zenna: That's an authenticity thing. You know? Some people are just the same all the time. Some...
Rob Wilk: Fine, but I try very hard... I didn't mean to interrupt you, I'm sorry.
Warren Zenna: That is great. No, fine. All...
Rob Wilk: I try very hard to make sure that there's no dulling of enthusiasm just 'cause we're on video.
Warren Zenna: Right.
Rob Wilk: And by the way, something as silly as like, I put a collared shirt on today 'cause I'm doing this with you, even though it's not even gonna be on video. There's like, it's like a... Okay. But it's like a uniform in my mind. Like, get the...
Warren Zenna: No, in your brain, your context changes when you change your... You know, I completely agree with you, by the way. When you put on the right thing, you sort of perk up a little bit. You know, if I was still wearing my pajamas, I would have a much different attitude about this thing right now, you know? Yeah.
Rob Wilk: At that end, look, there is a reality. This notion that you and I can sit here on video thousands of miles away from each other, perfectly clear, hear you, see you, everything is like perfect, it's not going away. So I brought back the notion of an in-person sales conference this year, and that... You wanna talk about making a sale? You know how hard that was to sell into a remote or hybrid-friendly company like Yahoo? So just so you know, we have folks all over the country working remotely. They have offices too that they can go to, but there's no mandate or anything like that. I'm in the office today. I like to come to the office, but you know, I'm in the minority. But there will never be... You will never, ever convince me that getting the team together in person, however infrequently, isn't of the utmost importance and value. And how do I know that? 'Cause after we fought and fought and fought and finally agreed, we had everybody meet at this beautiful resort in New Mexico, hundreds of people that only knew each other digitally.
Warren Zenna: Yeah.
Rob Wilk: You should have seen just the first hour. All I did was myself and our leadership team, you know what we did? We got there early and we stood by the front door. And as the cars started to pull up and, you know, people were bussed in and some people came in this way and that way, all we did at the front door was greet everyone as they walked in. And you've never seen hugs and smiles and laughs and, "Oh my God, you're so tall. I didn't even know." And I'm not, I'm saying to other people, I'm tiny. And we hadn't even done a stitch of content yet, and I already was like, "This is worth it. This is it." So we can get into the ad tech side of it and what, you know, AI and automation brings, 'cause there's lots of good stuff, but I'm always gonna be on the side of, I fell in love with what we do because of the human business, so I just wanna have a balance. I don't wanna go all in one way or all in the other way. I don't wanna be a Luddite and say there's no tech. I wanna use the tech, but I want our sellers, you know, to always have as many human relationships as they can face to face. And we have to keep up with the tech, so we've launched a ton of different agentic tools that enable, you know, an agentic buyer to talk to an agentic seller. We're doing that today. I would put us in the category of like, we're ready. I don't think the buy side is fully ready yet. There's still a lot to like about testing. But you know, over the next 18 months, I think it will accelerate and, not or, and I still want my team out with clients looking at the whites in their eyes face to face. You can do both.
Warren Zenna: You certainly could. You certainly could, no doubt. I'm also fascinated by the tooling of the thing. I mean, you and I are both familiar with the spaghetti junction of all the systems that go into ad tech and the guts of it. How much of that's changing? I mean, I don't know. I haven't done it in such a long time. I've been kind of out of the space, but how are the systems of record and all the things that get done and the technologies and the layers and the, you know, the attribution layers and the delivery and the DSPs and... How much is that going to be retooled with AI? Is it all gonna become just one big thin layer, or is it still gonna maintain this like multi-disciplinary and multi-technological stack? What do you think?
Rob Wilk: You're gonna see a massive simplification of all stacks. Yeah.
Warren Zenna: It seems a little flattened to me. I mean, it just seems like it, right?
Rob Wilk: It has to. And AI.
Warren Zenna: Has to.
Rob Wilk: AI is the accelerant. Like I see it 'cause, you know, Yahoo owns a DSP. We see it on our own DSP, but then you look at all the other, you know, big players out there, they're all making announcements and they're all taking that stack. Amazon just announced literally yesterday, like, "Give us your budget and we're gonna run it across all different places and you have no control over it, but you'll get the outcomes you want." Versus like, "Give me a budget for search, give me a budget for social, give me a budget for CTV, split it up into this, this, and display, and then we'll optimize it that way," and it's gotta pass through, you know, all these different jumps. Like you will see flattening of it. And I also think, go back to how we started this conversation. My mantra here, whether it's on our DSP sales team, we also have a sales team that sells inventory on Yahoo. You wanna buy Yahoo Sports? We have a team for that, you know?
Warren Zenna: Yep. Mm-hmm.
Rob Wilk: My mantra is like, friction free. Friction free. Because what's happening in, at least in our industry, but I'm assuming it's beyond advertising is as things get more automated, even pre-AI, a lot of the buy side was being asked to do more with less, more with less, more with less.
Warren Zenna: Always.
Rob Wilk: Right? So when they're in that scenario, and I was on the buy side, I saw this. Sometimes your decision isn't, especially as an agency, isn't, "I'm gonna do decision A because it is best for my client's business." And they go, "I'm gonna make decision A because it's just easier for me."
Warren Zenna: It's just easier.
Rob Wilk: And nobody wants to say that out loud. Obviously, a client doesn't wanna hear that. But I saw lots of decisions on the buy side being made because someone already works till 11 o'clock, and if they do that, now they work till midnight. And they're not interested, like Maslow's hierarchy like...
Warren Zenna: I like... I get it. Believe me, I went through this too. I had teams, they would tell me the same thing. They would say, "We just wanna work with these guys 'cause frankly, it's just easier." It's not necessarily better, it's just easier, you know? And I would tell those partners, I'd say, "Look, we're not using your system mainly because it's just too hard to use. Like, if you guys would simplify things, we'd use it all the time. So your product is actually quite good, but honestly, make it work better. Make my team's work easier, you know, stop it already," you know? And I think that AI is gonna do that, 'cause you're just gonna obviously start speaking to stuff and it'll just do things. I think too, the other thing too is I think the precision of the media itself is gonna get better. I think right now it's like all the... a lot of the guesswork will go out because the intelligence layer of knowing like the intent and the audiences and stuff will probably get more precise. But it'll get... I think it'll get smaller, but just more precise. I think that the problem is that we're doing a lot of... We're still doing the, you know, big audience to try and find the small. I think it's gonna flip around. We're gonna be able to signal more people who are buyers easier than we could before, and I think that's gonna make an interesting thing. We're seeing some companies doing some of this stuff right now with AI.
Rob Wilk: Yeah, I think there's extremes on both sides, right? There is this notion of like just mass reach, I don't care who it is, all the way down to, yeah, I got the right people, but there's only six of them and I can't scale it.
Warren Zenna: Hmm?
Rob Wilk: I think our job is to be right in the middle. That says you still have to get people interested in your product and there's still demand for work that needs to be done, and it will manifest in other things. You said you're in search. That's a lot of times where demand manifests through search. But you always see clients that get excited about reaching this really small audience and it was so hard to find and we've got them, and the next call is always, "Now what?"
Warren Zenna: Mm-hmm.
Rob Wilk: So I think you have to meet in the middle. But what AI will do and is already doing is if there's 60 steps to send a brief, plan it, decide who you're gonna buy, execute those buys, optimize those buys, report on those buys, like those 60 steps, you know, should become five.
Warren Zenna: Yeah, for sure.
Rob Wilk: And it will very, very quickly. We've already seen it within how we manage at Yahoo our own campaigns with our clients. You know, there's certain steps that we have fully automated, so there's people that still watch it and there's still rules that it has to follow, but there's a bunch of unsexy but necessary things that like folks on our team have to do to get a campaign live and again, to optimize it, report on it, and we are systematically just hammering down all of these unsexy but necessary parts so that they focus really on what matters, which is make sure the client wins first and Yahoo wins second.
Warren Zenna: Yep. I love it.
Rob Wilk: That's the job.
Warren Zenna: Well, that's good. That's a great way to close this conversation. So a little one more question is like, if you weren't doing this, what would you do?
Rob Wilk: Well, I think I hinted at the beginning. So I was a teacher right out of college.
Warren Zenna: What were you teaching? Like high school?
Rob Wilk: No, I was a special ed teacher for developmentally disabled adults.
Warren Zenna: Amazing.
Rob Wilk: I always say this, like, I'm not sure that there's a huge difference between selling and teaching. Like, they feel the same to me, except teachers get the summers off, which I don't get, but sellers get paid better. That is the dream. I wanna go back to teaching. I have no idea what, where, or how. I'm sort of envious of what you do in the sense of like, you get to work with people and teach them how to be great CROs. Like there's something in this notion of teaching others and like really passing it or playing it forward that I'm looking forward to someday. I don't know when that'll be.
Warren Zenna: But I get you, and that's why I do this because, similarly, you know, I was a CRO and I had a horrible experience. It was really bad. And you know, of course, like every CRO that has a bad experience, so I blamed everybody except myself, and it took me a while to go, you know, that was really actually all my fault. Like, I took the wrong job, I had no idea what I was doing, I made all sorts of stupid decisions, and boy, if I knew better, I would've probably done a lot of things differently. And then what didn't I know? And then how many CROs are having the same experience right now? And how many of them are in fact also at the mercy of a system that they inherit that they have no authority to change, and they don't know what to do about that? So how can we solve that, right? So for me, it's just teaching two entities to work together better. How do we get the organization and the CRO to understand, like, what the mission is and how to organize a system that works that it happens? That's pretty much what I'm trying to do. That's the whole goal.
Rob Wilk: I think it's important, amazing work. Good for you.
Warren Zenna: Well, thank you. Thank you so much for doing this. It was great, and we'll see you soon.
Rob Wilk: All right. Talk soon.