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Scalable

17 Sep 2026 · 48m · 27 chapters

Episode artwork

Inside Two OG Internet Brand Comebacks: Yahoo and Expedia Bet Big on Creators

In short

The episode of Scalable covers how legacy internet brands are regaining relevance with creators and social-first marketing. Yahoo’s CMO Josh Line explains Yahoo’s “every pixel is new” product rebuild and a creator-led marketing push to reintroduce Yahoo to younger audiences, including an AI answer engine beta called Yahoo Scout.

Key claims

creators provide trust and help Yahoo show up in culture; campaigns are measured by brand funnel, brand equity, and business metrics. Examples: Cardi B for Yahoo Mail’s AI Planner feature (FOMC “fear of missing something important”); Yahoo Weather with Kyle Cook (“weatherboy”) and a “party forecast” inside the app; TikTok-style “tech accessories” like a fake grass keyboard and a “scroll stopper” ring.

Expedia’s CCO Lori Metros details a year-long iShow Speed partnership: a 15-hour live travel marathon across five countries, then “shoppable storytelling” via a microsite to drive bookings.

Key claims

calculated risk in unscripted live works; authenticity drives search surges (e.g., Cape Verde). Examples: phase 2 microsite booking flow; plans to integrate booking into live via partners; broader creator/ambassador programs including B2B and employee ambassadors.

Guests

Josh Line (Yahoo CMO) and Lori Metros (Expedia CCO).

Written by AI. May contain mistakes.

Chapters

0:46

The State of Legacy Brands

Discussion on the relevance of legacy brands like Yahoo and Expedia in today's creator economy.

“Yahoo is more than 30 years old at this point.”
1:47

Yahoo's Comeback Strategy

Exploration of Yahoo's efforts to regain cultural relevance, including a partnership with Cardi B.

“to think that there are now people who don't know Yahoo.”
3:06

Expedia's Innovative Partnerships

Expedia's collaboration with iShow Speed to boost its brand through live streaming.

“We want to kick off with your partnership with iShow Speed.”
4:33

The Risks and Rewards of Live Streaming

Lori Metros discusses the challenges and benefits of partnering with creators in live streaming.

“The whole purpose was to sort of break into that cultural relevance.”
7:02

Engagement and Audience Building

Discussion on how live streaming and creative partnerships can drive audience engagement and relevance.

“And that's what makes his content so interesting.”
8:29

Evolving Travel Marketing Strategies

Details on Expedia's strategies for converting engagement into bookings through creative storytelling.

“And I think for so many people, especially Americans that were new to the World Cup, he brought them in.”
10:41

Future Partnerships and Brand Strategy

Insights into Expedia's approach to future partnerships and the importance of ongoing engagement with creators.

“like we're working with other partners that are very familiar in this space because Xfinity as a brand, that's not our like strong suit.”
14:00

Searching for Travel Inspiration

Learn how travel inspirations are sourced from various media and creators.

“second, but even when you watched the World Cup and Cape Verde was such a big thing, the searches went up so significantly to Cape Verde.”
15:00

Strategic Partnerships in Travel

Explore the importance of strategic partnerships over one-off collaborations.

“And sometimes that performs even better than just working with a big name celebrity.”
16:00

Influencer Trips: Trends and Backlash

Discuss the recent backlash against influencer trips and their relevance in travel marketing.

“like Revolve and Tarte and Shein were getting just a couple of years ago.”
Show all 27 chapters
17:00

B2B Influencer Marketing Strategies

Understand how B2B influencer strategies differ and their growing importance.

“come to us because they want to go travel somewhere.”
18:00

Empowering Employee Ambassadors

Learn about leveraging employees as brand ambassadors in travel marketing.

“But like we're working with corporate Natalie.”
19:00

B2B vs B2C Marketing in Travel

Explore the differences in marketing approaches for B2B and B2C in the travel sector.

“but then now they're partnering with TikTok on their sort of employee creator program.”
20:00

Navigating AI in Travel Marketing

Discover the role of AI as an accelerant rather than a threat in travel marketing.

“So that's something that we've been testing out a lot as well, too.”
21:00

Building Consumer Trust in Travel

Understand the importance of trust in the travel booking process and its impact on marketing.

“But corporate Natalie is so interesting because she has a whole agency on B2B.”
22:00

Creating Personalized Travel Experiences

Learn how personalization is integrated into travel marketing strategies.

“How do you think about AI more broadly from the marketing perspective?”
23:00

Storytelling: The Heart of Marketing

Explore the significance of storytelling in marketing and how it enhances brand communication.

“but we have put together as a company, a very small type group that is focused on search and how it comes up.”
24:20

Lessons from CBS Applied to Expedia

Gain insights into how experiences in entertainment shape marketing strategies at Expedia.

“There are tools and stuff that you can do to make things go faster, if it's vetting processes and all of that.”
28:00

Wrap Up of Previous Discussion

Recap and transition to new guest

“So I always encourage big thinking as well.”
28:22

Yahoo's Legacy and Current Transformation

Discussion on Yahoo's history and recent product rejuvenation efforts

“And for a lot of people in the 90s and the early 2000s, Yahoo literally was the internet.”
29:16

Marketing Strategy with Creators

Exploring Yahoo's marketing strategy focused on creators

“And for Yahoo in particular, the last couple of years have been super focused on reimagining all of our core products.”
30:59

Budgeting for Increased Marketing Efforts

Discussion on how Yahoo is ramping up its marketing budget

“And so creators are very much a core part of our strategy.”
33:48

Engaging Creators and Brand Representation

Insights on Yahoo's collaborations with various creators

“Like what are the characteristics that a person needs to have in order to be characterized as a Yahoo?”
36:19

Wiping Social Media: A Fresh Start

Josh explains the decision to reset Yahoo's social media presence

“Sometimes, you know, our goals are a little bit more limited.”
38:00

Innovative Marketing Campaigns and Humor

Discussion on Yahoo's creative marketing campaigns and their impacts

“but then it's also all the new people who had not heard from us and seeing us show up with a point of view and with a brand voice that is the thing that I think is the essence of Yahoo.”
40:19

IRL Events and Brand Engagement

The significance of in-person events in Yahoo's marketing strategy

“And that's actually one of the things that's always like sort of a unique challenge.”
42:00

Yahoo's Strategy for Cannes and Creator Partnerships

Learn how Yahoo revitalized its brand presence at Cannes by engaging creators and the audience.

“Again, that's like a core part of our strategy as well is getting back out there in real life.”
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Transcript

Automatic transcript. May contain errors.

0:00Hi, everyone. This is Scalable, a weekly show about the business of the creator economy.

0:04Jasmine Enberg: I'm Kaya Yurieff. And I'm Jasmine Enberg. Every Thursday, we take you beyond the headlines to tell you what's happening, what it means, and why it matters. Who is a better person than Aisha Speed that has like 140 million followers? His main vertical is travel, and he has never partnered with a travel partner. And so we thought, this is just a match made in heaven. I don't think you're the only brand who feels that way about live streaming because it is so unpredictable. Anything can happen live. I mean, there was some behind the scenes stuff that we were like, oh my gosh. The thing about creators is they're a great way for us to get back out there, to be reintroduced to an entirely new audience.

0:46Jasmine Enberg: Yahoo is more than 30 years old at this point. A lot of times we get out there and people would say, Yahoo, where have you been? We're going to get to that.

0:58Hi, Jasmine. Hi, Kaya. And hi, everyone. Welcome to Scalable, our weekly show about the business of the creator economy. Jasmine, you've been in New York this week.

1:08Jasmine Enberg: I have. I'm still here. As you can tell, I'm sitting in my hotel room. But it has also felt like literally everyone else in the creator economy has been in the city this week as well. I mean, there's the first ever IAB creator friends. There's also the podcast movement industry event, as well as the first Sounds Profitable Business Summit. And I was actually there on Monday interviewing Maggie Sellers-Ream of the Hot Smart Rich podcast. And we'll share more from that conversation in an upcoming episode. Today, we're going to share our recent interviews with two legacy internet companies, Yahoo and Expedia.

1:40We spoke with executives from both companies all about how they are modernizing their brands through creators and social media.

1:45Jasmine Enberg: Okay, I have to say it is crazy to think that there are now people who don't know Yahoo. I mean, in the 90s, it was basically the internet. And obviously, the company has had its ups and downs since then in 2000. During the height of the dot-com bubble, Yahoo reached a valuation of$125 billion. And then by the time it was acquired by Verizon in 2017, its value had cratered to just$5 billion. So we recently sat down with Yahoo's CMO, Josh Line, to discuss what it takes to bring the OG internet company back to cultural relevance. He discusses the company's recent campaign with Cardi B and how they managed to turn universal inbox anxiety into a viral moment.

2:26Speaking of dot com survivors, Expedia is another one. It was spun out of Microsoft in 1999 and popped during its IPO. It's still a popular option today when people want to compare prices and book travel, but it's facing heightened competition and a new threat with the rise of AI. Expedia just wrapped the second phase of its partnership with top live streamer iShow Speed, who despite being known for his high energy travel live streams, had never teamed up with a travel brand before. Expedia's chief communications officer, Lori Metros, joins us to break down how the risk of diving into live streaming is paying off in a big way and how they're now tapping into creators in other areas as well.

3:02We're so excited to have you, Lori. Thanks for coming on. We want to kick off with your partnership with iShow Speed. So you just launched the second phase of a year-long partnership in June. So tell us a little bit about it. You know, why this partnership? Why him? And why now? It's something that's totally new to Expedia. Like we've been working in the creator space for some time, but we haven't done it at the level that we were with iShowSpeed. And the way that we sort of approached it was like, we really wanted to do more of like a strategic partnership than just working with a big macro talent.

3:38And so one of the audiences that we were looking to capture was Gen Z. And who is a better person than iShowSpeak that has like 140 million followers? But even more importantly, his main vertical is travel. And he has never partnered with a travel partner. And so we thought, gosh, this is just a match made in heaven. Why wouldn't we do this? And so like you said, we have a three-part partnership with him. The first was a live stream, which was 15 hours. I don't know how much of it you caught, but I was like, oh my gosh, how can I watch 15 hours of this? He is so entertaining. It was like, I think I probably watched about 12 of the 15 hours live.

4:26It was crazy. So interesting. But it was awesome. And he went to five countries in the Caribbean. The whole purpose was to sort of break into that cultural relevance. And we saw a major surge in search for the countries that he went to visit. It was unbelievable. And so for us, it's like identifying authentic partnerships, I think, is like the biggest thing. And when we wanted to capture that audience and work with somebody that loves travel, we couldn't think of a better partner. How did you decide on the places? He did. So when we first approached this, we've been working on this for quite some time before it started.

5:07And Expedia has never, first of all, done a strategic partnership at this level. But also live is a whole nother element, which is like a very scary space to play in. We just felt like it was just the perfect, perfect partnership.

5:23Jasmine Enberg: I don't think you're the only brand who feels that way about live streaming. Like we hear that time and time again because it is so unpredictable. Anything can happen live. And one of the things that your team told us was that it was a risk to do this partnership, the phase one that's live and unscripted, because you can't edit iShow Speed. So what made you decide that the risk was worth it in the end? I think for us, the way that we approach anything is we do a lot of vetting on the front end. And so for us, we did that. We have that discipline and we go into it. We do all the vetting and we knew that this was going to be a risk, but it was like we were weighing the risk and reward.

6:05And so we kind of were very clear. He knows he's working with the big brand. And so we were very clear that we didn't want to take away from his storytelling process, nor was he interested in that. Once we got to the point where we're like, okay, we're comfortable with doing this. We know that things can happen, but as a brand, we're comfortable with doing it. We let him go and we let him do his thing. And I think that's why it was so magical and it worked out so beautifully.

6:31Jasmine Enberg: Were there any tricky moments or anything that you wish you could have edited out in the end? Or was it all kind of what you were hoping for and expecting? There was some behind the scenes stuff that we were like, oh my gosh, where planes didn't necessarily go according to plan. And I think it was more stressful on his side because he knows when he sets the clock with his viewers, they're expecting him to go live. But his team is so well trained that they know how to sort of combat all of that stuff. I think the scariest part of he watched it at the end, he was like, oh, my God, I'm going to a fifth country.

7:07And then he passed out. I don't want the live. And we're like, oh, my God. But he did it and he made it through. And it doesn't like 15 hours of live. This guy goes at it. He is on. He does not turn off for one second. And that's what makes his content so interesting.

7:27Jasmine Enberg: So he passed out. And then did you have to call like an ambulance, a medical team? Did he just wake up? Like, how did that result? He just like went down for a couple seconds. You can see it live on the stream. I have to go watch that. Literally at the end, he hit his fourth country. He made a decision. I'm going for five countries because he constantly wants to break world records. And all of a sudden, as he's walking out, you see him sort of like stumbling a little bit. But he caught it and he went on and he just kind of, I think stuff happens to him because he puts himself out there so much.

8:02That's what makes him so interesting.

8:04Jasmine Enberg: I got to see him at the first World Cup game here in LA because he was there too filming and he was still going strong. I mean, at the very end of the game, we happened to exit at the same time, which was really fun. So I saw him kind of jumping over all the banisters and the barricades and all that. And it was just it was nonstop. He filmed the whole time. And that was only like three or four hours. So like 15. I can't even I can't even imagine. Listen, I love the World Cup and I watched all the World Cup. But he was such a good ad. And I think for so many people, especially Americans that were new to the World Cup, he brought them in.

8:38He brought them in and made it so interesting in a different way. So, yeah, the energy is crazy. Is Expedia all in on live streaming now or are you still going to be cautious moving forward? I think it's less about live streaming as it's about the right partnership that we want to do. Because I got to tell you, after we did this, so many creators have come to us and so many platforms have come to us and said, you guys have cracked the code. Do you want to do it with others? And it's hard to do anything as great as I show speed. So for us, it's about, Is it the right person? Is it the right platform?

9:15Walk us through kind of the second phase. So we had this marathon live stream with him. Tell us a little bit about phase two and kind of how shoppable storytelling worked in with that and what that is, because that's not a term I think people are necessarily familiar with. Every time we approach something, we need to figure out sort of like, what do we want to accomplish? And the first part with the live stream was totally reach and relevancy. That was our goal with it, which I think really helped us. And then the second part was, okay, now people want to, how do we convert them into the booking process?

9:46So we created a microsite. Everything was in partnership with his team because they know exactly who his audience is and how to bring them in to how the microsite actually looks and the content that was on there. And so basically we created this ad where people could travel like speed and then they can go book it. And it was an amazing commercial of all the fun stuff that he does. But then people could actually book those experiences. And now we've seen even an extended life beyond that where we're working with other creators to capture the travel life speed stuff and make that process bookable too.

10:27And then I think the third part, which we're working on right now, will be a way to integrate both where there'll still be a live streaming component, but we're already training the audience that then you can go if you like it to go ahead and book it. Like directly in the live stream? Basically on a live stream, like we're working with other partners that are very familiar in this space because Xfinity as a brand, that's not our like strong suit. It's like, how do we go into a YouTube thing? So we're working with VaynerMedia on that part and also Mothers. What we've learned with all this live streaming stuff is the clip, and you guys probably know this with your guys' show, the clipping is such a big part of it.

11:04And so there are ways to take it and extend its life and get that scale and reach through the clippings and people can book it. So it's not like you're booking it when you're doing it. It's afterwards. Yeah. I mean, there's so many different elements now too. It's not like, okay, we do the live stream and that's it. There's clipping. There's still traditional advertising. So how did you think about all those things with the second phase of the partnership? We worked with his team so closely and with a lot of our agency partners to figure out like, how do we capture this in a way? Like clipping for us, we've never done.

11:33We've never really had long YouTube series that you can go ahead and clipping. So that space is so exciting to me, actually, as somebody that also sort of manages not only our creator space, but the social ecosystem. How do we get more familiar? Because that's how I watch stuff all the time. I feel like I watch an episode because I've seen a clip. So it's just that things are changing so fast and you have to get in front of people. And I think it's such a cool, unique opportunity for us.

12:01Jasmine Enberg: So now that booking is the goal, I mean, you said that in phase one, it was about reach and awareness, and you obviously had some great results in terms of search. Is there anything you can share in terms of the results? Has it led to an increase in bookings for you? I think for us, when we walk into a partnership with somebody at his level, that's the gravy. It's not the end goal. Even when we do a second phase, which is about booking it, it's not ever the end goal to working with somebody like that. So for us, it's like just even how many more viewers we have is such a big part of it. And getting people into our actual booking process is part of it.

12:40It's like breaking down the funnel. There's no funnel anymore. And so you have to be able to integrate everything into one. You've obviously done other creator partnerships and you hinted at some others. So what can you kind of share about upcoming partnerships and also how you decide who to partner with? Obviously, you have iShowSpeed, who's a major name, but are you also working with kind of smaller, more niche creators? How are you thinking about who to partner with? It's such a layered approach. The other cool thing we did this year, and I don't know if you guys saw, but we partnered with Ken from Barbie.

13:10and he was an influencer for us as well. And we actually looked at that partnership as like an influencer partnership. So you could travel like Ken. It was the first time he had left Malibu and he's going to experience the world. He went all over the world and we did a huge Super Bowl commercial with him too, which was a way to break into culture. I mean, I'm going to have to send it to you. It was huge. huge and you know for us it's about like doing stuff that's unexpected which I think is kind of what we did with Ken it's like it's one thing to partner with Barbie it's another thing to go experience when Ken leaves Malibu for the first time and how is he experiencing the world which is kind of how speed looks at stuff too when he goes on different places I'm gonna backtrack for second, but even when you watched the World Cup and Cape Verde was such a big thing, the searches went up so significantly to Cape Verde.

14:12So I think people are looking for this inspiration in so many different places. If it's through the media, if it's through social, if it's through creators, they're just looking at different inspiration and trying to find things that are different. But to answer your question, we're sort of looking across the board. I think when we go into these bigger partnerships. We're not interested in like one-off partnerships, doing an ad and leaving it there. It's really about how do we do something strategic with them? How do we partner with somebody that may be more engaged in media where we can get the awareness?

14:48So we're looking for people that are very integrated into the travel vertical, that have a passion for travel. We have an ambassador program, which is global. And for us, that's some of our top performing content that we have. And sometimes that performs even better than just working with a big name celebrity. You have to build trust with your audience. And we feel like the best way to do that is through creators. And then you need that local relevancy. Like you want people that live there and experience it to show up on our channels. And then we have our scale, which is more of our micro. And we do that as more of the commerce aspect of it.

15:26Like how do we bring people into that shoppable through scale. So it's a very multi-layered approach that we look at our creators and we're investing so much more in it because we've seen so much upside both on social with our paid, the conversion with creators, we see that performance is so much better and in our product too. Okay, we have a little bit of a spicy question for you because influencer trips are back in the spotlight now.

15:54Jasmine Enberg: There was one that OpenAI hosted in upstate New York. It got a lot of backlash from people online, and it reminded us of the backlash that brands like Revolve and Tarte and Shein were getting just a couple of years ago. At the same time, though, you know, it does feel like a travel brand is the right fit for an influencer trip. Obviously, you're traveling around the world with iShowSpeed. What is your take on influencer trips? Do you think brand-hosted trips are in, are here to stay? Oh my gosh, so spicy. Thank you for that. You know, we don't do influencer trips for the sake of influencer trips.

16:32I think Virgin like put like a thousand creators on a Virgin cruise ship. And I think that worked really well for the brand. The way that we look at it is very differently. Like I mentioned to you, we have an ambassador program. The way that we do that is that's an education. We want people, we know they love travel. Now we want them to be educated into what our brands stand for, what our brand propositions are, what our products are, all of that. But that's not an influencer trip. For us, it would be more about a lot of people come to us because they want to go travel somewhere. Or even talent come to us and say, we're going here.

17:07Can we go through Expedia? I've seen the backlash. I think, you know, I mean, it's everybody's brand. We don't have to do it, as you said, because we're not a product. We're wanting people to experience the world. And so it's a little bit different for us. So zooming out, a lot of these partnerships have been kind of focused on B2C and reaching consumers, but you also have a B2B business, which is growing much more quickly than B2C. So how do you kind of work with creators on the B2B side or how do you envision that? Oh my gosh, I love, love that question because that is such a focus area for us right now too.

17:40We actually are working with a lot of B2B influencers. We're working with like LinkedIn, for example. We have three brands. We have Expedia, which is sort of our marquee brand, the one-stop shop, everything in one place. We have Hotels.com, which is exclusively hotels and they cater to a lot of businesses. And then we also have the Vrbo brand. But like we're working with corporate Natalie. We have a full campaign on hotels.com where we're working with like real people. And so for us, it's like our B2B powers a lot of travel brands. And so that's an education thing. But we see so much value in B2B influencers too.

18:22So that's definitely been a shift for us and another focus area that we're looking to tap into. And our employees, that's another thing everybody's talking about. You know, we actually are going to have a whole employee ambassador program as well, because they know our products. Most of the people that are at Expedia love to travel. So why don't we use them as well? So that's what I'm saying. I think for us, it's not a one size fits all. You have to do everything.

18:49Jasmine Enberg: Tell us a little bit more about the employee program. I think we're hearing that from mostly like retail brands and restaurants at this point. I mean, Starbucks came out with, I mean, they've had the Green Apron program for a while, but then now they're partnering with TikTok on their sort of employee creator program. Gap obviously just launched one. How are you thinking about this? And when can we expect to see this program go live? Well, by the way, we haven't announced it. It's something that I've been thinking about a lot because I think there's a lot of value. And I've heard so many, even on our organic social art creator team, our creators.

19:22And so they are so embedded. Even our product team, we have found some people that are really good storytellers. and they know our products better than anything. So as you're talking to B2B and stuff, there's also that education of how our products work. And so we feel like it's a good way to do it. But like, we're still early days and we are most likely going to launch it in the fall. We're working with all the platforms too, because obviously they see huge value in the creator space and working with brands like us. So they're all offering their creative programs to us to be able for us to scale even more.

20:03So that's something that we've been testing out a lot as well, too. You have creators, you have customers, you have employees. All of these different types of creators can bring such a different perspective and point of view. How different is it, especially with travel marketing, when you're working with like a B2B creator? I think corporate Natalie, we had her on the show recently, too. I mean, she's someone that I think bridges worlds as well. But when you think about B2B marketing for travel versus B2C, what are the biggest differences, especially with the creator strategy?

20:30Jasmine Enberg: Like, are there certain things that you have to highlight for B2B travel versus B2C travel that you might not think about? Yeah, I think for us, it's more of an awareness play in B2B because one of the things that we do in our B2B space is we power travel for so many different partners. We made a big announcement with Uber a couple months ago. We're basically powering the travel behind Uber Travel. And so a lot of the times that's other brands, but we're the people behind it. So I think from a B2B perspective, for us, it's about more of the awareness of what we do and what we can deliver and what our marketplace looks like than going out there to talk about different brands and stuff like that.

21:14But corporate Natalie is so interesting because she has a whole agency on B2B. And so she works with us on Hotels.com. And we're about to do a big campaign with her agency and do something really fresh and different talking about Hotels.com. So we're trying to let our creators and we decide feel like our good fit for our brand kind of do their thing versus trying to be too prescriptive. And that was the same with Speed. It's like, I think if we gave him so many roles, it wouldn't have been so great. Corporate Natalie, it's like, here's the brief. It's a tight brief. go and make it happen, you know, and let them sort of put their magic to it too.

21:53Jasmine Enberg: So speaking of platforms and partnerships a little bit, I mean, Expedia was also one of the first brands to put ads in ChatGPT pretty recently. How do you think about AI more broadly from the marketing perspective? How big of a threat is it to what you're doing? And also just more broadly, how big of a threat is it to Expedia overall when you do have more people who are researching travel on ChatGPT, for example? We looked at AI as an accelerant for our business. It's not going to replace a lot of what we do, but it's definitely going to help us build and scale a little bit. And so for us, the philosophy is always be wherever the consumer is.

22:33And so if that's in ChatGPT or some of the other lands, we want to be there because we want our brands to surface up. What we also found is like OpenAI, they announced that they wanted to do travel. There's more than just booking. There's different currencies. There's insurance. It's a very, very complicated business. And so not everybody can do it. So our philosophy has been, we're seeing social and AEO sort of be our fastest growing channel, but we have put together as a company, a very small type group that is focused on search and how it comes up. But we're also focused on it from our product perspective too, which is why would somebody come to Expedia to search?

23:20How are we connecting the discovery and the search back to our product? And so we're looking at ways to also have more proprietary content within our product as well. On that level, we are playing with everybody because we think that it's important and that's how people are doing it. But then they're not booking necessarily there. They're searching, they're discovering. We did a really interesting program with Meta where we understand like, how do we connect search and then bring people into the booking? And so we did this thing called trip matching where if you saw a reel of anybody, it could be me and you click the arrow to Expedia, we'll post a whole itinerary for you and then you can go book it.

24:04So we're always looking at ways to connect from sort of that discovery phase back into the booking phase. We're also looking at it even on the creator space. It's never going to replace our creators because I think travel, you have to have that trust. No one wants to see a fake place. They want to see a real place. There are tools and stuff that you can do to make things go faster, if it's vetting processes and all of that. And so that's where we see the real value. And it's early days. It's early days, but like we're excited about it.

24:35Jasmine Enberg: Plus you have to build that trust. travel is not a cheap purchase. And it's something that people spend a lot of time researching before they ultimately make the booking. And if you think about AI platforms, in particular, I mean, they really haven't built up that trust yet with consumers. And now we're even seeing research that shows that it's kind of hitting its lowest point in terms of trust among people. So, you know, I think that probably played a lot into sort of how we're seeing the strategy that these AI companies develop. I mean, for example, OpenAI backed off of, you know, travel booking and in-app purchases.

25:08Jasmine Enberg: Like obviously people are still researching to your point, but you can't really book an app anymore. Yeah. I think trust is, is the cornerstone of what we do. And I think that you nailed it because travel is such a high consideration. So somebody may save it for later when they're ready to go book something. You may not see an immediate result. So, you know, it's hard to make that direct correlation that this is that's why booking is a component and we need to bring people in. But it's not at the end of the day, you're not going to see those results automatically because of the high consideration and the long tail of booking travel.

25:45And you want the social proof, right? Like AI can kind of summarize some stuff or I find it helpful for summarizing reviews, right? But like, I'm still not gonna just make a purchase willy nilly without some sort of simple proof. And that's why we have to do it even better on our product. And that's what we're investing on on our product. AI is helping us with the personalization. So if you come back to Expedia, you want them to remember who you are and what kind of hotels. So you get served up the stuff that makes sense for you. And so those are all the things that are actually going to help us with AI and make us move quick.

26:22But it's really that personalization. Oh, wait, to wrap up a little bit, You've had such an interesting career. I mean, before Expedia, you spent nearly 18 years at CBS. You went from junior publicist to EVP of comms. As we're seeing media and marketing continue to converge, I mean, what are some of the lessons that you've taken from your time at CBS that you kind of apply to your work now? I love that I came from entertainment because at entertainment, you think big, you have all these big ideas. And I think some of the things we're seeing is come back full circle. So I learned a lot coming to a tech company.

26:54But the big ideas. And I think people, we saw it at Ken Lyons, right? Like people want in real life experiences. And so that with creators and working with talent and coming up with strategic big campaigns that can break through. I always said, it's like, it's not a sprint. It's a marathon. How do you create that sort of sense that people care and make these big strategic campaigns? And And so I love that entertainment. I think it made me a great storyteller. And I think that's the thing to take away is how do you tell a good story? And that's why we look at creators. That's why we look at everything we do, even on a comms level is how can you tell a good story for a brand and also to take risks, quite frankly.

27:40Like I, and I, and I think speed is the perfect example of that. Like I always say to my team, be able and not, don't be afraid to take a risk because that can help you so much with your career. but take a calculated risk, right? Like don't take a risk for the sake of taking a risk. But my whole career, I think I've made my way up the ladder because I haven't been afraid to take chances and sort of go against the grain. So I always encourage big thinking as well. Oh, that is a perfect note to end on.

28:09Jasmine Enberg: Thank you, Lori. Now it's over to our conversation with Yahoo's CMO, Josh Line. Hi, Josh. Welcome to Scalable. We're so excited to have you. Thanks for having me. Nice to be here. So Yahoo is more than 30 years old at this point. And for a lot of people in the 90s and the early 2000s, Yahoo literally was the internet. We were actually talking about this recently. Kaya, wasn't your first email address a Yahoo email? It was. It was kaya papaya10 at yahoo.com because I was 10. I love that. I love that you put the page in it. That was the thing. It was the thing. I wish I still checked. Like, can I still access that?

28:48Is that possible? I'm not sure. I probably could help on that.

28:52Jasmine Enberg: I unfortunately was not a Yahoo girl. I was a Hotmail girl. I was on MSN Messenger a lot at the time. And so I feel like everybody there was on Hotmail, but I was Dance Girl 073, I think. Maybe we chatted at some point on Hotmail. Yahoo's one of the OGs of the internet, right? We've been around 31 years. I've always loved the challenge of taking a great brand and rejuvenating it and bringing it back into culture. And for Yahoo in particular, the last couple of years have been super focused on reimagining all of our core products. We like to say that every pixel is new because every product in our portfolio has either been rebuilt, new features, totally reinvented.

29:33We're sort of on this product journey first and foremost. But of course, the Internet, a lot has changed, right? The next leg of the journey, the next, as our CEO likes to say, the next level of the video game is marketing. And we've got a ton to work with. I think one of the things people sometimes underappreciate about Yahoo is its scale. We are in the AI era. And that's why Yahoo earlier this year launched into beta Yahoo Scout, which is our entry into the space. It's our AI answer engine. And for me, coming in from a marketing perspective, it's really about relevance and getting back out there and inviting a new generation of Yahoos into the family.

30:13Jasmine Enberg: I love that you went there because our first question was literally going to be, there's a lot of moving parts when you're trying to reinvent a brand of this age and really bring it back into culture and conversation. And where do you start, which you told us is, you know, at the product side of things. But now if you're thinking more about the marketing strategy, obviously, you've been doing a ton of work with creators who are very much in the culture, in the conversation. What does your creator strategy at Yahoo look like now? One of the things I love about marketing is just, you know, like every five years, like the playbook just sort of fundamentally changes as platforms and channels evolve.

30:47And creators is obviously, you know, one of the more foundational changes that's happened within marketing. And so the thing about creators is they have trust with their audience. And so they are a great way for us to get back out there, to be reintroduced either to our existing audience or to an entirely new audience, especially a younger audience. And so creators are very much a core part of our strategy. We're using them in everything from brand campaigns to product marketing to community engagement. And, you know, we've sort of doubled down on them, even insofar as almost treating them as a channel, a scaled channel for us in our efforts.

31:24So as you've been kind of now going into the marketing phase and kind of turning up the volume on that, what does that actually entail? Does that mean increasing budget? You know, as you're doubling down, what does that look like in terms of budget, too? Sure. It's definitely an increasing drumbeat. We were dormant a few years ago from a marketing perspective. And so we've been ramping. 2025 was sort of first step. In 2026, I think our cadence has really increased throughout the year. And I think you can totally expect that to continue in sort of all different sort of magnitudes of that, whether that's something really small and lightweight, like so many of the kind of creator partnerships we do on a one-off basis, to something much more significant that feels like a kind of bigger campaign.

32:07This spring we worked with Cardi B in a campaign for Yahoo Mail. The Yahoo Mail was launching a new feature called Planner. Planner is basically calendar, task management. It's an AI-powered feature, so it reads your inbox and can tell you if you've kind of missed something in the body of the email. We coined a term, FOMC, fear of missing something important. Everybody knows that feeling of like, oh no, what did I forget to do? And it was like buried somewhere in the email. Coined a term, and then we thought about who could represent this? Who's like the busiest multi-hyphenate out there? Cardi happened to be about to go on tour while we were shooting this.

32:41And she's doing it all. She's like a busy working mom, kind of a perfect representation of it. And I think in working with her, we try to put everybody that we work through through the simple filter of like, are they a Yahoo? Do they share that sensibility, that brand voice of Yahoo? I want to know Cardi B's Yahoo email.

33:04She was fantastic to work with, by the way. But it was kind of a social first campaign, although we had other channels as well. But, you know, top performing in every dimension, highest viewed, highest engaged. You know, the organic on it was just insane before we even put a dollar against it. It moved the needle on the product side, which I think is the signal we always look for, right? Is the engagement we're seeing online translating into product performance? And we saw, you know, our app store rankings for Yahoo Mail increased significantly. search behavior, utilization of the feature. So, you know, that through line of how we're measuring the impact of the campaigns, but kind of great example of our playbook and how we think about putting the pieces together.

33:48Jasmine Enberg: So Cardi B is a Yahoo. Who else is a Yahoo? Like what are the characteristics that a person needs to have in order to be characterized as a Yahoo? That's a really good question. They gotta be in on the joke and like down to, sometimes we just phrase internally down to clown. Another great example, we are in fantasy football season right now. And we partnered with our G3 for our back to school campaign. Basically, fantasy football. Obviously, most people play kind of pro fantasy football. So it's pro games. But Yahoo Fantasy this year is introducing college. So college play and a college game. And so he's a Heisman Trophy winner.

34:23He's got a great personality. He was a blast to work with. But there's so many others. A small example, we partnered with this guy, Josh Eckert, who was sort of blowing up because he would take these walks outside and he would describe them as crispy fall mornings. He's got a really fun sensibility. And we partnered with him for Yahoo Weather. I think the weather space is a space that's super interesting because creators are really playing this new important role when it comes to weather. And a lot of it's bringing personality to it. Also utility, but certainly personality. And I think we've been tracking that dynamic pretty closely.

34:59And so this summer, when we launched the new Yahoo Weather app, we partnered with Kyle Cook. Reality fans out there, Kyle Cook is a star of Summer House. He also has a line of ready-to-drink adult beverages called Loverboy. So we cast him as our weatherboy. And, you know, hilarity ensued. We shot a ton of content with him, basically being our weatherboy, both in the studio and out on the street, and actually also in the product itself. So we basically had a party forecast. Because like in the summer, one of the things that you're thinking about is if I'm having that barbecue on Saturday, what's the weather going to be like?

35:31We created actually within the product custom sort of party forecast within the product. And then when we launched it, we had an event with a bunch of other creators to kind of get the work out about it. And again, another example of like the pieces lining up and us really seeing not just the engagement across social, which this was our number two performing kind of asset in the history of us doing this. But also product performance, like app downloads up 170%, people coming back twice as often to the app as they were before. So we're really seeing that kind of product utilization piece.

36:06Jasmine Enberg: Is that the end goal of these campaigns? Is it really the product performance? Are you doing this more for awareness? I mean, I think everybody's heard the brand name Yahoo at this point. How do you approach the creator strategy that you have? And is it different depending on the partnership and the person you're working with? It does vary for sure. Sometimes, you know, our goals are a little bit more limited. We're always thinking about the sort of just a simple idea of culture, brand, and product, right? And how we put those pieces together. And so whether it's something very product-centered like that or something lighter, like we partnered with this creator, Scott Mirrorhead.

36:42He's sort of a self-proclaimed remote work guy. And he built a desk out of sand for us that you could send emails from. So it's like fun, lightweight social content gets us out there, gets us in the cultural conversation around summer and work and those kind of universal insights that people have around technology. I'll give you a community engagement example. By the way, we had wiped our social feeds two years ago. We're going to get to that. Yeah, we're going to ask you about that. When we first started, you know, a lot of times we get out there and people would say, Yahoo, where have you been?

37:13A creator did this. It was like sort of a, I would call him like a dad comic on TikTok. And he made this joke about his wife having a Yahoo email address. It was late. I thought it was late. But our client saw it and fired off into the comments a very funny retort, which was, you know, we've been taking care of your wife for longer than you have. With the obvious implication that, you know, our reply has over a million likes and like thousands of positive comments. and I think it was a great example of like, especially in the early days, like getting back out there, not being afraid, owning who you are.

37:49And by the way, the best part is when you go into the comments and this happened with Cardi and it happens every time we get out there, you will hear people say Yahoo for life. I love Yahoo. It's people who are Yahoo users who are standing up for us, but then it's also all the new people who had not heard from us and seeing us show up with a point of view and with a brand voice that is the thing that I think is the essence of Yahoo. It's got this just incredible brand voice. It's unlike anything else in tech. It's like, it's really unique. So, I mean, the name is Yahoo, right? So we got to show up that way.

38:21Jasmine Enberg: What does your legal team have to say about those cheeky comments on social media? Yeah, do they require approval or is that like an ask for forgiveness situation? We have a great working relationship with them. You have to in order to, you know, take some swings. So let's talk a little bit more about that. Because two years ago, you wiped social media feeds, started over. That's quite a dramatic move. So walk us through that decision. And what does the social strategy look like now? The first six months, we called it like pilot season, because it was like, let's just try a bunch of stuff and see what works.

38:52Because, you know, there wasn't really a playbook for like an internet brand showing up on social organically and doing brand work and doing culture work in that way. There just wasn't a good reference. There's lots of other industries where there's like great references for like how you approach these things. One of the things that was really interesting that resonated, you know, we put out a post on April Fool's, which April Fool's is always like a, you know, tricky environment. Kind of the worst. It was like, don't do it unless it's really, really good. And we have this idea, this kind of ongoing series of, we call them tech accessories.

39:28And they're just like fake products that we sell on the TikTok shop. They just give you something sticky to work with. The first year we launched a grass keyboard and we treated it as if it was like this heroic product launch. It was the meme of touch grass. We just made it real. And people absolutely loved it. It just like completely blew up. And I think it resonated because it's like, it's a simple insight about like, the keyboard warriors needing to take a break, right? And get offline. How many people bought them? Like, how did sales go for this? They sell out in like an hour, everything's gone.

40:00What does that mean in terms of like units or revenue figures? It's a good question. I don't remember the units that we sold. It's not like we do a few hundred of these things. It's mostly, you know, for the content and, you know, it creates engagement. It's just getting back out there. Yeah, and you don't have a physical product. Right. We don't have a physical product. And that's actually one of the things that's always like sort of a unique challenge. When you don't have a physical product, it's sort of about like the feeling you create with what you've put out into the world that makes it sticky, that makes it entertaining, that brings you in to deliver the product messaging if that's what you're doing.

40:33This year, we call it the scroll stopper. I mean, everyone's familiar with the rings and all the, you know, sort of optimizing your metrics. But what if the device prevented you from actually scrolling? It looked very absurd on your finger and we rolled it. It was sort of shot like a Nike ad kind of thing. But really the whole joke was like, hey, stop doing scrolling, get off and do something, you know, do something better with your time. So, you know, that's a great example of like these kind of obvious tech cultural insights that we're just trying to tap into. What was up with the Caviar collab?

41:05These ones I understand because they go with tech, but the Caviar one was different. Tell us about that one. Sometimes the connection is a little loose. Caviar has been having a moment. Everyone's tracking it. And the big thing with Caviar is bumping Caviar or you put it on your finger. And that sounded to us like just bumping this up, that email behavior when you're like, you've sent an email, you haven't heard back. And I'm like, just bumping this to the topic room box, which no one likes that version of bumping. So just a fun, lightweight collab.

41:34Jasmine Enberg: So one of the things you said there is that you're getting back out there. And speaking of that, the other thing that you've been doing a lot recently is leaning into IRL events. You were at Cannes Lions recently. You were also at the Music and Tech Festival, FWB Fest, and with creators. I mean, you brought people from Alex Heath to Emily Sundberg. I saw Taylor Lorenz, who we both know, was also at one of your dinners. So why this? Why now? Like, how important is it for you to be showing up IRL at these types of places? It's so important. Again, that's like a core part of our strategy as well is getting back out there in real life.

42:11And, you know, something like CAN this year in particular, the theme of our activation was Yahoo Explorers Society. That harkens back to our mission to be the trusted guide through the digital wellness to help people achieve their goals. But it also very squarely relates with Yahoo Scout. Scout inspired our thematic this year. Think Jacques Cousteau meets the Life Aquatic. Cannes is a creativity festival, so we want to show up in a really creative way. We don't just want to have a corporate activation. We had a purple submarine, and in the morning you could get iced coffee out of it, and in the evening you could get some rosé.

42:42The other thing that we did this year for Cannes that was really exciting is we leaned into creators and LinkedIn in particular. And so we had a series of content call. We partnered with four creators. Emily was one of them. that we called Scouted at Cannes. And it was just like digests from the things that our creators were seeing, our tastemakers were seeing on the ground in Cannes, the thematics, and we rolled that out across LinkedIn. FWB is this amazing festival. It was our first time participating. We hosted a dinner. And so many interesting people at the center of, or it's sort of at the intersection between technology and creativity.

43:20So we hosted a dinner and it was themed, I love the internet. and one of the things we did at the dinner was we asked everyone to share an artifact from their their history with the internet that they loved that they want to bring forward into

43:36Jasmine Enberg: the future of the oh give us a few i need to hear the best ones oh gosh there were so many so many interesting ones people who had had their own blog like would talk about something a post they've made 15 years ago that had some special significance. I'll tell you what mine was. I had worked at Comedy Central. When I first started, we were kind of revamping our overarching digital strategy, reorganizing. And it was kind of in between one era of the internet and the next era of the internet. It was sort of at that moment where the internet was changing to being social first, right? I remember we put out this video clip from the show Reno 911.

44:18one. I don't know if you remember that show. And it got like 150 million views. It went totally viral on Facebook, got 150 million views. And it was this absurd clip, very, very funny. And the thing that stuck with me was that comedy is rocket fuel. And so the internet of the future, like I very much want it to have that personality to be funny and wacky and wild. And I think so often creators, they leverage that insight too, I think.

44:44Jasmine Enberg: The creators that you were showing up with, at Lisa Ken Lyons, like Emily Sundberg, Alex Heath, these are also creators who've built a lot of trust. These are more newsletter writers, they're journalists. How does that kind of play into what your strategy is with them? Their trust, their authorities in their areas, right? That is one of the ways in which we very much are strategically partnering with creators, especially around Yahoo Scout. The deepest consumer need when it comes to AI and answer engines and AI search is trust. Can I trust the answer here? And so that is an important role that, you know, those authorities are bringing to the table for us.

45:23We think about creators through that lens. Like, do they have authority in the space? I would say the other thing can is a B2B moment. So B2B marketing oftentimes, you know, I don't know, we've all experienced B2B marketing. It can be pretty dry, pretty boring, pretty formulaic. And for Yahoo, we're like, you know, we have a DSP ad tech product. We have a Yahoo ads business. And we want to show up with all that brand personality in those spaces, too, because it cuts through. So for the Yahoo DSP, DSP, it's a pretty it's an ad tech product. It's a pretty involved kind of sale to get someone on to a DSP.

46:00We partnered with this creator. He's a British creator named Troy Hawk. And he does these fun man on the street compliments, like real time compliments. And we cast him as our performance aficionado because DSPs are all about performance. Yahoo DSP performs incredibly well for clients. And we brought him to CES. We brought him to Cannes. We shot content with them. We used our own DSP to run a campaign targeting potential buyers of a DSP. So we're a big believer that B2B marketing does not need to be boring and leverage creators in unexpected ways.

46:35Jasmine Enberg: I got to say, this is the first time I've ever heard of a creator partnership for a DSP. I mean, I've been covering the ad industry for a long time, and it's never come up before. So very clever. So as you, you know, work to kind of bring Yahoo back into cultural relevance, what does success look like? Like, where do you see Yahoo one year from now, five years from now? Some of this is vibes based, right? Like to be in the zeitgeist, it's, you know, there's some numbers and things that can back it up. But how are you thinking about all that and measuring your progress? We are measuring it in all the ways you would expect us to be measuring it.

47:07We're measuring it through the brand funnel. We're measuring it through brand equity metrics. We are measuring it through business metrics. And I think our overarching objective is momentum, right? Momentum against all of those metrics. And certainly we've got some momentum at this point. We want to build on that. You know, stepping back from it, you know, I think we're on a path as a company. Thank you so much, Josh. We so appreciate the time. Thank you so much for joining us. See you back here next Thursday.

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From the publisher

Two decades-old internet brands are getting back into culture through creators. In this episode, Kaya Yurieff and Jasmine Enberg sit down with Yahoo’s CMO Josh Line and Expedia’s Chief Communications Officer Laurie Metrose to talk about what it actually takes to be top of mind again.


Metrose walks us through Expedia’s biggest creator bet yet: a year-long partnership with livestreamer iShowSpeed, built around three phases that combine livestreaming and shoppable storytelling. 


Yahoo’s Line discusses the company’s comeback strategies, such as a Cardi B campaign for Yahoo Mail that turned inbox anxiety into a viral moment, Kyle Cook becoming Yahoo Weather’s official “weather boy”, and the reply-guy moment that landed Yahoo millions of likes after the company had wiped its social feeds for a fresh start.



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