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- [00:00]
Rob Wilk
Oh, hello.
- [00:01]
Jeremy Bloom
I'm Jeremy Bloom, co founder of marketexture. And has anyone told you how chaotic our industry really is? It is absolute chaos. It's never been harder to predict the future of advertising than now. Cookies are going away. AI is knocking on the door. Regulatory oversight is shifting. Consumers are changing the ways we receive content on an hourly basis. So let's cover these topics together. We welcome you to join us at our first Market Live conference where we're bringing together the smartest folks in advertising to talk about the chaotic nature and how to prepare. Join us on March 17th in New York City. Please go to Marketurelive.com and register now.
- [00:43]
AdTechGod
Welcome to the Ad Tech Godpod, your window into the world of advertising technology and the people behind it. I'm your host, AdTechGod. Welcome to the AdTechGodPod. Your God. Go to for conversations with sales leaders shaping the future of our industry. I'm thrilled to have Rob Wilk, Yahoo's Chief Revenue Officer. Rob brings a ton of experience from his time at Snap and Microsoft, where he really made things happen. Fun fact though, he was already a part of the Yahoo family back in 2008, so it's awesome to have him back for a new and improved Yahoo. In my opinion, Yahoo is cool again and it's great to see them back with so much personality and vigor. I'm excited to have you here with me today, Rob, welcome to the ADTech Godpod.
- [01:31]
Rob Wilk
Thank you, sir. And that is a hell of an introduction. I appreciate it.
- [01:35]
AdTechGod
Of course, I appreciate you being here and thanks to the team for getting this scheduled. I love speaking to sales leaders because in my opinion, they bring such a different perspective on the market and what they see. So I'm really looking forward to the second half of the podcast and hearing how you see the market moving into 2025.
- [01:52]
Rob Wilk
Sounds good, Rob.
- [01:54]
AdTechGod
Like, take us back. Like, how did you, how did you reach the point you're at today? You're obviously chief revenue officer of Yahoo. Yahoo's a sizable company, a big player in the market. I'd love to hear about your career and how you reached this point and how you got into a tech in the first place.
- [02:08]
Rob Wilk
Yeah, I will try my best to be brief, but it's a 30 year career, believe it or not. I'll start with my first job in advertising was at a very storied ad agency called Young and rubicam. In the mid-90s, I was a media assistant media buyer on the Dupont Lycra account, which I knew absolutely nothing about. But I really loved that role. I loved that job, but realized in the first two years that with the help of my then boss that I was on the wrong side of the table. I shouldn't be a buyer, I should be a seller. And she was super supportive and helped me find my first sales job which was at a publishing company called Ziff Davis. So Ziff Davis is known for PC magazine and a whole bunch of other tech magazines. I did that for a few years. But I think for this audience, hopefully the most interesting thing is in the late 90s. One of my favorite career highlights is I my first digital sales job was in the late 90s. It was at a company called tunes.comt u n E S like music tunes and whattunes.com. there's actually a Chicago based company. What they did was they did deals with publishers and said, look, you don't know anything about the Internet. And that's, you know, this mysterious thing in the late 90s. Give us all your content, we will build your website and we will sell all the advertising on it and we'll give you a cut. Our big flagship was Rolling Stone. So I was the first salesperson ever@rolling stone.com we also had a hip hop magazine called the Source and a jazz website called Downbeat Jazz. That was like one of the most exciting things I've ever done in my career, selling this new thing called the Internet. And the funny thing was getting a meeting when you say I'm from Rolling Stone.com was very easy. We had the most ironic challenge and I'm sure we'll get into this, but we had an incredible brand name with absolutely no supply whatsoever. So the first few ed deals that we did, we basically sold out the website. It didn't have any traffic. So that was a super, super fun experience.
- [04:06]
AdTechGod
I work for a publisher early, early on in my career and we kind of experienced the same.
- [04:11]
Rob Wilk
I mean we did, we did quarterly deals and then, you know, imagine a month into the quarter, you've got two months left and you have nothing to sell. It was crazy.
- [04:19]
AdTechGod
Yeah, that's rough.
- [04:20]
Rob Wilk
And obviously, you know, there weren't the ad dollars then that there are now, but you also didn't have the supply then that you have now. So I absolutely love that. And actually this probably will go into. One of the things we'll talk about is like, you know, matter what you do, you have to listen to the market. You have to know what's going on. I worked at Rolling Stone for a couple of years, but I kept hearing about this new idea, this new company, and this is really going to take you back. But it was a company called Goto.com that eventually rebranded as a company called Overture.com which was really the first instantiation of any type of biddable or programmatic media. And they were on fire. In fact, I had clients calling me, telling me they were cutting my display budget in because they wanted to go all in on this thing called paid search. Did my research and basically figured out who the head of sales was. And no joke, I cold called her and said, I want to meet you. I think you want to meet with me. I want to see what you're doing. Very long story short, I ended up being employee number six in New York for this company called Goto that had just rebranded to Overture. I think for this audience, I think one of the coolest things that I learned was, you know, prior, when I was selling Rolling Stone, it was always, hey, what's your rate for this? And I would quote them a rate and then they would come back and say, I don't want to pay that rate. And you'd negotiate. It was all a game, right? What I loved about Overture was advertisers can bid whatever they want. And for the folks that really go back, you'll remember this at any moment, you can go to overture.com and you can type in any keyword. Let's say you want to search for who's bidding on the term watch. I'm just making that up. Not only could you see who was bidding, but Overture in those days actually showed you transparently what the prices were that everyone was bidding. You know, this is again, 23, 24 years ago. This was like completely, like revolutionary. That company, Overture ended up being one of the first really big Internet acquisitions that got bought by none other than Yahoo in 2003 for about 1.3 billion. And I just love that model mostly because in that model, everybody wins, right? If you're the advertiser, you pay what you want. If you're the user and you search for a product, you get the results that you're looking for. And in those days, Overture and then Yahoo got basically paid a fee to make the introduction between buyer and seller. And I absolutely just love that model. And, you know, I did that for a while, worked at Yahoo, went to a startup called Foursquare, eventually to Microsoft, where I spent, you know, eight years in that time with Microsoft. You know, a lot of your listeners will know this, but Yahoo and Microsoft have a very long standing, very large, you know, multi Billion dollar search partnership. That's where I got to know Jim Lanzone, who is currently the CEO of Yahoo. Because we worked very closely together when I was at Microsoft. And he's always someone I've admired. He's always someone that I've just liked and got to know. And I'm very blessed that about a year ago we started talking about rejoining Yahoo, and I joined in June of last year.
- [07:23]
AdTechGod
You're not the first person, and I truly believe in this as just me. The relationships you build are so important. Don't burn any bridges. I think some people do. Some people are not very pleasant to work with and they regret it later on because it's really having that relationship with your manager, whether that's the CEO or it's a sales manager or director, that really can help you progress in your career down the line because they'll come back and pick you up. I mean, one day you need a job and you call them and say, you were incredible to work with. Come work with me again. Help me build the team. Help us expand this product. So I love that he. He scooped you up and brought you back in.
- [07:59]
Rob Wilk
He didn't have to convince me very hard, to be honest. I thought it was such an amazing opportunity. But I love the point that you're making because, you know, right now, Yahoo is. Is rebuilding a lot of its tech, a lot of its sales processes, salespeople. And you would be very, hopefully, pleasantly surprised to see how many boomerangs are coming back to Yahoo. Whether they left five years ago, 15 years ago, 20 years ago. There's so much sort of industry love for the company and industry love for the brand that, you know, much to my pleasant surprise, there are so many folks that have rejoined Yahoo in the last year, two years, that are boomerangs.
- [08:38]
AdTechGod
It's funny, I remember Yahoo. It's a name that. That I feel takes me back to the beginning of the Internet and at least very early on. So when I saw you guys had the Yahoo button for sale, the Yodel, I bought one. I'm sure you saw the picture. I was like, right away, I'm like, oh, a $25 or whatever it was, I'm like, I'm buying one. It's incredible because the nostalgia of the brand is there. And now with all the acquisition, the expansion, and what you guys are doing with your partnerships, Yahoo seems to be back. Like, it's. It's back on the market. I'm hearing about it constantly. You have a great team. I know Gabriel over there. If he's listening. Gabriel's a great person, but you have a fantastic team over there that's working really hard.
- [09:18]
Rob Wilk
Obviously, I agree with you and I appreciate the sentiment. Maybe what I'll add is, you know, I, I've said this for so long. I've sort of joked like, I'll probably never do it, but I always fantasize about, like, if I was going to write my own life story of things that I've seen and done not just in my career, but in my life. My favorite joke is, like, my story would have more exclamation points in it than anyone else you'll ever meet. I happen to work for the one brand that has an exclamation point in the actual brand itself. And I know it's such a small thing, but to me, it's actually a huge thing because it allows us to be a little bit different. It allows us to be a little bit more irreverent. You know, we don't have to follow the same path. And I think Yahoo attracts people who are like that.
- [10:03]
AdTechGod
I think the personality and the, the brand image comes through.
- [10:10]
Rob Wilk
I actually love the way we're viewed.
- [10:12]
AdTechGod
I agree. Yeah, I think it's a very good branding and it's a very good personality for the brand. I think it's super important.
- [10:18]
Rob Wilk
And your point, by the way, is not lost of, you know, if you go back to the years, you know, go back pre. Programmatic, all, all of those days, you go back to late 90s, let's say the first 10 years of 2000. I can't say ought. I'm sorry, I just can't do it. It doesn't feel natural. But like, there are people who were working with Yahoo, whether it was, you know, a client, an agency, or even working at Yahoo that, you know, 20 years later now are in very senior roles and they have such love and, you know, respect for the company. And so many of the folks who have worked at Yahoo, at one point or another, I always say this, like, they always talk about ELON and the PayPal mafia and I'm like, who's going to write the book about the Yahoo Mafia? If you look at some of the biggest names in our industry, so many of them have spent time here.
- [11:04]
AdTechGod
Rob, question for you. You've. You've obviously been really, really successful in your career and leading a strong sales team at Yahoo. What do you think has been the biggest highlight for you, though? You seem very happy and enthusiastic about being back at Yahoo, but what do you think is the biggest highlight that you could share with us today.
- [11:21]
Rob Wilk
Well, I think I touched on one which is just the industry reaction from Yahoo or clients, longtime, you know, people that I've worked with when I told them I was going back. The universality of positivity around, I love that move for you is very, you know, candidly, like, very gratifying because I'd worked here before and there was a long period in between, so many people said, oh, you're back at Yahoo. Is it just like it was before? And I was like, no, not at all. There is the same sort of vibe that's hard for me to articulate. I think it has to do with, again, the type of people that choose to spend their time working for Yahoo. You know, I find the people here to be similar to me of, really proud of the brand, have a lot of love for it, feel very deeply personal about it. I just, I'm struck by the fact that. And I, I think, I think Jim, you know, deserves a lot of credit here. He sets the tone from the top, which is like, what we look for are great human beings. First, of course, we want them to have the skills, we want them to have the experience. But he really is effective at finding people that are just great humans. You know, there's so much cross collaboration that has to happen across the company and so many different properties. And our dsp, I can go on and on. So you have to find people that are sort of innately collaborative and enjoy working with lots of other people. And I, I must say, like, that's been so much fun to come back to. I care so much about who I work with, not just what I do.
- [13:02]
AdTechGod
Yeah, you have a, you have a no jerks allowed policy.
- [13:05]
Rob Wilk
He's no joke about it.
- [13:07]
AdTechGod
Yeah, I mean, that's like the best policy you can have. You know, everybody works hard, everybody collaborates. There's. There's none of this politics. Let's just get work done and let's succeed together. It's like the ideal situation for anyone.
- [13:19]
Rob Wilk
I can give you a really good non Yahoo example, which is I joined Microsoft in 2015 and this was right after Satya Nadella had his first year. So he was still like a relatively new CEO. And lots of the folks that I worked with would tell me stories about the pre Satya era, where the brilliant jerk was the king, where they reigned supreme. And Satya, again, you have to give the man credit. For 200,000 employees, you know, it didn't change overnight, but slowly but surely, he changed the culture. He basically said the brilliant Jerk is no longer acceptable. And that's, you know, not an easy thing to do at a company that big. And I saw it firsthand. It was really true.
- [14:01]
AdTechGod
It's incredible how much one individual or one department can impact the overall morale of a group or of a company. It's so important that your employees are happy and motivated and collaborative. You can have one really, really smart person, but that person isn't going to carry the weight of 2, 300 people or even a thousand or 2,000 employees or 10,000 employees. Like, you really need cross collaboration between departments to grow. And if you have someone that's difficult, it makes it difficult for everybody.
- [14:29]
Rob Wilk
I'll be super honest. Many years ago, I used to think once a company gets big enough that one person can't really impact, right? Like, it just becomes so big that it just becomes its own organism. And again, seeing Satya do it change my total perspective on what is or is impossible. That's how like, impactful it was.
- [14:50]
AdTechGod
This is coming off of CES is a couple weeks out before I release it. AI was a really big topic, obviously, lots of partnerships happening and it was like a flood of press releases over the last week or so. What trends in the industry are you really like, bullish on and just positive about overall?
- [15:08]
Rob Wilk
Yeah, I mean, you mentioned AI and I know that, you know, every time I bring it up, I could see the eyes roll of, here's another person talking about AI. What I'm trying to do to get that message to really land is like, I don't spend as much time in the theoretical. I like to spend time in the actuals. So if you look at what our DSP is doing, just as a simple example, with a product, basically a suite of products called Yahoo Blueprint that is all AI driven optimization that is geared towards better outcomes for advertisers. It's very simple. We're super transparent. When it works, we show it to them. We show them the money they saved, we show them how much more they can spend in working media. So I like that example on the DSP side, but AI is now woven throughout every Yahoo product. And again, I'll be super honest here. If you look at Yahoo Sports just as an example, I personally am not a huge Yahoo Fantasy or fantasy player in general, but I know lots of my friends are die hards. My brother has like six different leagues. He's the commissioner of three of them. He always wins like two to three leagues a year. And I like using the example of when you're doing your draft, Yahoo. Has AI that can help you make decisions every single week. You have to pickup players or drop players, and you're always looking for that. Sleeper AI does that for you. You know, those are simple examples of, of AI at work today. I can only imagine if you and I were to do this a year from now, how much will have changed. I think some people are sort of intimidated by the topic because it's so big and it's so broad and it's so wide. I'm just trying to go out and get simple examples for people to understand that you're seeing this in your everyday life. It may not say, hey, here's your AI of the day. It may not be that overt, but it really is taking hold. The last thing I'll say is, I think an area that no one talks about, and I know you'll relate to this, is I'm actually super passionate about AI for the sales team, which is not something that people speak a lot publicly about. But I know if I look at my team and I look at how much time and energy can be saved and then redirected towards focusing on advertisers, outcomes and business, this industry in general will benefit everything from. You know, there's always like, you know, CRM work that every salesperson hates to do. There's automation for all of that. You and I should be able to have a meeting where we're only focused on talking to each other. And in the background, there are agents that are transcribing the conversation, putting that information into somewhere that is, you know, chattable, scannable, queryable, however you want to put it. It should be able to look at an advertiser's campaign and make recommendations. All of those things should free up our time to be able to do the work that we all think is the most impactful, which is driving results. So we're doing a lot of that work. And I think from what I'm being told from, you know, other publishers, like, we're sort of leading the way here. And I'm. I'm, like, pretty bullish on that one.
- [18:19]
AdTechGod
It's funny. One of my questions is, what's something that people in the industry disagree on? And I think there's been a lot of. Again, I. I like to focus on the positive. The negative gets so much airtime is what I've noticed. Like, we're an industry that really likes to complain a lot. It's unbelievable. It's like you sit down, you look at, you look at a website, you look at LinkedIn and if there's one negative piece of news, like, people run with it for weeks on end, but nobody focuses on the positive. And for AI, there's been a little bit of a negative perspective. For some people, they're focusing on how this may be a risk to my role, this may be a risk to my job. Maybe they're going to automate it. And even I think just a few days ago, Meta announced that a lot of mid manager engineers might be replaced by AI. But the reality is, is that AI is a tool. It's a tool just like Microsoft Office or email. Like, these are tools that we should be able to be familiar with. If you don't know how to use AI and you don't know how to write the right commands and get the right output out, or integrate AI with your workflow, or integrate AI with your, your sales pitch and how to utilize it, that's where you're at risk. But if you become familiar with it and you use it the right way, it's really like a cape for Superman. Like, it's incredibly beneficial to my daily work and I'm sure yours as well.
- [19:37]
Rob Wilk
If you don't want to adopt these technologies, you don't have to. But if you're worried about being replaced, you can guarantee you will be. If you don't know how to use these tools, there's just no other way to put it. I told you, I came from Microsoft. Can you imagine people that were doing calculations on a calculator saying, I'm not using Excel. You know, we can talk about the quality of it, whether you like it or not. This, for some weird reason, spreadsheets are polarizing. But anyone who said, I refuse to use this found themselves out of work anyway. That's the truth.
- [20:09]
AdTechGod
What do you think keeps you in the industry?
- [20:12]
Rob Wilk
You just mentioned we're coming off the ces and it's hard not to be struck by. Every year I forget this until I go back to ces and then I'm reminded for a tech conference where so much of the conversation is about things like AI, like automation, you know, the different interesting uses of technology, I think maybe because I'm just so. I feed off of the energy of people. You know, I give a lot of energy. Hopefully I. I receive a lot of energy. I'm struck by the same thing every year, which is the hugs and the laughs and the high fives. Just even walking, meeting to meeting, I'll stop the 30 seconds and see someone I've known for 20 years. You know, I love the people I don't know how else to put it. I think we're one of the most fun, interesting, ever changing, you know, industries. And for whatever reason, marketing, advertising seems to attract people that want to do great work, want to do interesting work, and are unapologetic about the fact that this industry is fun.
- [21:20]
AdTechGod
It just is.
- [21:22]
Rob Wilk
I mean, I'm talking to EdTech God right now. Name another industry where you could have done what you have done and, and, and have a success.
- [21:33]
AdTechGod
I know it's pretty crazy in the.
- [21:34]
Rob Wilk
Insurance business or in the accounting business, but you do it in advertising and you've been embraced and that's just great example.
- [21:42]
AdTechGod
It's been incredible. I think, you know, ending off the year 2024, which was pretty bumpy for many. You know, I saw a lot of posts about saying, I don't go to CS and I hate cs and it's exhausting. I think people write that, but when I see them there, I could tell you a majority of the same people who said, I can't stand this event, we're having fun, having dinner, grabbing drinks, sitting at tables, playing golf. I'm like, how do you hate this? Like, it's exhausting. There's no doubt it's an exhausting trip, especially coming off a nice, you know, sometimes 10 day, two week break and getting right back into it. But it's incredible event to just meet up with people and talk about what's happening the next 12 months.
- [22:21]
Rob Wilk
I am exhausted from that week, but both things can be true. I loved every second, every client meeting, every hello in the hallway, every meal. I don't know who, how has time to play golf. You have to introduce me to those people. But, you know, all the way through to, you know, we had, we had an event Wednesday night with, you know, 50 Cent performing and the place went bananas.
- [22:44]
AdTechGod
It's pretty incredible.
- [22:45]
Rob Wilk
It was so much fun. So the combination of like, yeah, of course you're not doing ces, right if you're not exhausted at the end. I was exhausted on the flight back to New York, but I had ear to ear smile. I love the way we showed up. I loved, you know, interacting with all of our partners and clients and advertisers. You should be exhausted. That's how you know you did it. Right?
- [23:06]
AdTechGod
Exactly. Rob, what do you do to keep yourself happy? Yes, the industry's fun. The people are amazing. A lot of our friends that have, you know, industry friends become personal friends and you start, you know, learning more about their families and their lives. But what keeps you happiness and how do you keep that balance between, you know, high pressure industry that's constantly changing and just, you know, leaving at the end of the day, being able to say, okay, I'm a happy person. I'm going back to my family to live my other life, which is my family life.
- [23:35]
Rob Wilk
Well, that's my first life, let's be clear. I've known my wife since she was 14. I was 16 when we met. She was 14. We've been married 21 years. I have three boys, only 17, 14. They are my reason for everything, period, end of story. And they know that. Honestly, I like the idea of balance, but not unlike the corny way. Let me explain what I mean. I am completely objective about what you and I do for a living. One of my very close friends is an emergency room doctor right near me in New York in a, in a place in Connecticut called Greenwich, Connecticut. And once in a while we'll talk about our days or what's happening and I'll say, oh, this advertiser is, you know, upset about, blah, blah, blah, and he's like, oh, well, I had to deal with a child who was in a bad car accident and lost both of their parents, right? And he has to, you know, deal with that. So I, I have, like, great perspective on. I love what I do. I'm hardcore. I work my butt off, but I'm pragmatic about that. Where I get, like, the real deep stuff is when I can help other people, whether that is my own team. I love to mentor, I love to give back. You know, I sat on the board of a nonprofit for a long time. I'm actually one of the newest board members of Ad Council, which is like one of the things that I've always wanted to do. And I've always admired what the Ad Council does. I hopefully everybody here knows, but basically they focus on causes, but they use donated media to get the word out about important causes that are happening in the world. They just do some incredible, incredible work. And it's just run in such a professional, sort of heartfelt or heart led manner. And I'm finally, you know, a part of that and I can't wait to, you know, to do more. So I like to balance things that we achieve at the company or things that my team achieves or that we achieve together with. I'm always looking for ways to like, pay it forward or to give back to other people. It's so funny. It's a little bit perverse because I get such pleasure out of helping other people and people view it as, like, wow, he's a. He's like an altruistic guy. They don't realize it's, like, innately a selfish endeavor. It makes me feel good to help other people. So I do it. And it sounds ridiculous, but, like, it's the honest truth.
- [25:53]
AdTechGod
No, I don't. I don't think that's ridiculous at all. I mean, I think that behind the scenes, and I was probably a little bit more vocal and open about it, but that's a lot of what I was doing in the beginning. I was posting a lot of people looking for work because I was lucky enough to be working. I was sharing their resumes and their links with people that I knew because my network expanded a thousand fold with this account. And many times they're like, let me know if there's anything I can do. And my response would always be, don't worry about it. Like, go feed your family. Like, that's what matters. I don't necessarily want anything in return. Just go get a job and be happy and live your life. And that's all that matters in the end is. Is that your.
- [26:33]
Rob Wilk
Your.
- [26:34]
AdTechGod
Your family is in a good spot.
- [26:36]
Rob Wilk
I. I don't know how to agree with that any harder. I'll just say amen.
- [26:40]
AdTechGod
So you're obviously loyal to a brand like Yahoo, and I think a lot of people have the same feelings as you do. But is there a particular brand in the market that really stands out that's earned your loyalty? And I'd love to hear why it.
- [26:56]
Rob Wilk
Earned your loyalty besides Yahoo. Honestly, it feels like I'm dodging the question. I learned a lot at Microsoft, and maybe because it's just such a big company at one point, it was the most valuable company not too long ago. I really respect the people at Microsoft, and I think it's mostly because everybody there walks the walk. You know, they have a lot of good intentions. And I have so much respect for the Microsoft Team that I worked with, but also, again, for the CEO. I was really fortunate to get some exposure directly to Satya. And I just watched every word, every movement, every gesture, because I just thought he was incredible. That's the truth.
- [27:42]
AdTechGod
Well, Rob, I wanted to thank you for being here today. Thank you again to Yahoo for sponsoring Sweet Sweets in Las Vegas. We really appreciate you doing that. And also thank you for being my guest today on this podcast.
- [27:54]
Rob Wilk
It was truly, truly my pleasure. And thanks for having us. And if folks out there haven't watched the Sweet, Sweet series, it's so much fun. It's a totally new way, especially if you didn't go to CES to really experience the feet on the street sort of feel. So make sure you watch it.
- [28:10]
AdTechGod
Wait till we do. Hot yachts. Yes, that's happening. Haven't announced it. I guess I'm announcing it now. But Hot Yachts is coming.
- [28:19]
Rob Wilk
Well, we won't have a yacht, but we'll be on the beach and I. I hope you guys will be there. We'll.
- [28:23]
AdTechGod
We'll get a dinghy or something. We'll ride around in it. It'll be fun.
- [28:26]
Rob Wilk
We're going to call it the beach with Reach.
- [28:30]
AdTechGod
Awesome. Rob. Thank you. Thank you so much for being here.
- [28:33]
Rob Wilk
Thank you again. Appreciate it.
- [28:34]
AdTechGod
Thank you. Thanks for tuning in to another episode of the AdTech Godpod, a podcast for the people about the people. Stay connected with me for more insights, trends and interviews in the realm of ad tech. Don't miss out on the latest updates, so follow me on X Instagram and connect with me on LinkedIn. Don't forget ATG Slack community has insights, networking opportunities and jobs. Keep the conversation going and stay at the forefront of adtech innovation.