Interview #5: Kevin Weatherman

Advertising is a major part of society today, albeit less prevalent in the traditional retail world compared to other walks of life. I have been trying to get smarter about how the advertising world works, and I figured I was not the only one. 

With that in mind, I had the pleasure of chatting with Kevin Weatherman, from Upscale, about what he is building and the future of retail media. I am super excited to share this conversation. Thank you so much, Kevin, for taking the time!

This is the fifth conversation in an ongoing series with movers and shakers in the retail industry. Is there anyone you want to hear from? Please be sure to drop their names 👇

The following conversation has been lightly edited for context and clarity.

Noah Sobel-Pressman: Kevin, thank you so much for joining me today. For those who aren't aware, could you tell us more about Upscale and your background? 


Kevin Weatherman: Going way back, I graduated from Berkeley in 2004 and was looking for a job in the Bay Area. I ended up working at a limo company. One day, someone called from transportation at a company called Google. This was right around the time of their IPO. The person said we want to take 16 trips from the Bay Area to Mountain View every day to take our employees to work every day. I ended up signing a contract with Google to take all their employees to work every day. I got a very big bonus, and it was super exciting. [I wanted to learn more about Google, so] I asked my friend in banking, “what does Google sell?”. He says, online apps. 

After that, I started looking for startups in San Francisco, and I started at a company called Adbright. That was where I started my career in ads in 2007 in the Bay Area. Then I was the first person at PubMatic, which is a publicly traded ad tech company. From PubMatic, I joined a company called MoPub, since I saw all of my ad customers moving from desktop to mobile, and jumped in on the mobile bandwagon before everyone else. This was the end of 2010, early 2011. We built a business that went to a billion in revenue in 36 months. That was pretty amazing to watch mobile become the platform that it is. MoPub eventually got acquired by Twitter, and then from Twitter got acquired by AppLovin, and today it's the supply side of AppLovin's demand and supply business. From there, I stayed in SaaS and Data. 


I was at a company OneSignal, and decided to start my own company. I founded a Weight Watchers for men and learned how to do all the media buying for mobile app installs. Since then, I have worked on a few other companies. Most recently, one of those companies, Facet, got acquired, and as part of the acquisition, one of the companies that didn't acquire, but tried to buy it, was a company called Moloco. I ended up joining Moloco with my co-founder at Upscale to focus on initially on figuring out the supply side of television, and then we started focusing on the supply and the demand side of television. While working there, we started to realize that there was a huge opportunity to help figure out performance on television. 

Dovetailing into Upscale, Upscale is designed like Attentiv is, like Klayvio is, as a single solution for performance television. I go to Klayvio, I think about email for eCommerce brands. I go to Attentiv, I think about SMS for eCommerce brands. I think about Upscale as CTV streaming for eCommerce brands. 


The first thing that we focused on was how to drive performance. The big unlock that we kept hearing from interviewing customers was creative. That's when we brought in our cofounder, Mike Chang, who came from QuickFrame, who was a part of the MNTN acquisition. We would talk to advertisers, and they would love to run TV, but I don't have $100,000 to spend on the TV creative. [With Upscale,] we have now gotten that cost down to $500 in creative. Any brand that wants to work with us can just pay us $500 on creative, and we can make television commercials for them. We have really scaled up our ability to make television ads from an existing set of assets. We have an entire pipeline of products that we use to ingest those assets and turn them into high-quality television content. 


The second part of the business that we learned from being at Moloco was how to drive performance. We found that a lot of these brands [were focusing on], Meta, Google, and TikTok. Television is just such a low priority on all of the lists that brands think about. Brands wanted simple and easy. In response, we built “always on” creative, where we are constantly creating new creatives for the brands to drive better performance. We do the media buying for the brands that we work with, starting at as little as $500 a day for 2 weeks. For about $5,000, you can get started streaming with us. We also do the measurement, so with our Shopify integration, we can link the impression that is shown on a TV back to the individual Shopify order ID. For the brands that we work with today, we do performance television, where we handle the creative, the media buying, and the measurement. 


NSP: In addition to your advertising background, you have spent time in eCommerce.Could you share more about how you got into eCommerce?

KW: I backed into eCommerce through a mix of adtech and investing. When I was at Twitter, I was on the team that acquired Brian Long’s company, TapCommerce. After that, I ended up investing in Brian’s next company, Franklin Mobile, which became Attentive. That opened the door for me to spend more time around eCommerce and the Shopify ecosystem. I started investing in companies like AccelPay, Crstl, and GHST, and got to know a lot of founders building the infrastructure and tools behind modern commerce brands.

NSP: Could you share a little bit more about why brands should be investing in performance television and streaming ads as opposed to some of the other channels that you mentioned? 

KW: Coming from mobile, what we found was that any brand was willing to invest significant capital into a channel if they knew it could drive net new users. In a world where most brands are locked up with Meta, there are not many other new channels to drive net new consumers. You can do television, you can do podcast ads. There's just not a huge laundry list of channels that a brand can really invest in in order to open up that net new reach. Our thesis was that, as consumers, we are now at the point where the majority of [television] consumption is happening streaming. What we have seen in our career is that when a new channel opens, the first wave of advertisers is all brand. We are seeing that today with OpenAI, where people can go on with the platform and just do CPM-based media vibe. 

Where a platform really scales is if an advertiser gives you $1 and you can give me $4, $5, $6, $7, $8, $9, $10 back. That's when I basically have an unlimited budget that I can give to you. We saw this firsthand at companies like Moloco, where advertisers would give us $100,000 a week, and we would drive them a $1M in purchases. The ability for us to turn television into a channel that can scale like that, then allows us to help these brands grow, especially for net new users, users who might not be sitting on their phone on Instagram all day, every day. 


This is the channel that allows them to test that. Brands are able to test it if a channel works for you, for between $5,000 and $15,000. For most of the brands that we're talking to that are over $10M in GMV, the ability to test a new channel like this in a turnkey way is really exciting. The majority of the brands, about 80%, are seeing positive return on ad spend. It might not be the same as Meta, but it is positive enough, and it is a net new customer base. Because of the Shopify integration, we can see how many of the users that we order that we've driven are net new consumers, who've never interacted with your brand before, versus being able to bring back existing customers. 

The combination of what is possible today with the programmatic channels, within streaming, is, inspired by what we saw in mobile, as you've got more sophisticated, being able to segment the consumers, being able to put the right ad based on where they are in the journey. These are all table stakes in any sort of performance platform. We felt that whether it was the existing set of solutions out there, or even if you were a very large advertiser and you wanted to do all of this yourself with millions of dollars of television spend, there weren't any tools that made this easy. 
What we consider coming from the mobile world, like performance best practices, just weren't being adopted in television before we got started. 

NSP: Most of the audience of this newsletter are retail and CPG operators who might not be doing much on the eCommerce side or streaming TV. If they are doing TV, it is more focused generally on the brand, rather than driving to commerce. One of the things I've been thinking a lot about is the connection between content and advertising, with commerce. I would love to hear your thoughts on that statement. What are people missing by just focusing on traditional branding for TV and streaming advertising as opposed to trying to drive commerce more granularly? 

KW: For CPG brands, the assets that are going to perform well on television are probably similar assets that will perform well if you work with other eCommerce platforms’ retail media networks. Many of the advertisers that we work with, if they have a creative that's performing well, it also becomes an asset that they use on their Amazon stores, etc. 

When it comes to retail, streaming does have a place for retail. 
We work with several CPG brands that are using the fact that you can target individual zip codes to be able to focus on driving retail within an individual store. The way to think about that is, if I'm working with 1,600 stores for Target, there are probably 500 stores that I really care about driving sales in. You can look at your same store sales by zip code or by store and be able to say, here are the markets of stores that I care about and stores that I don't. You can run a material test to be able to say here's 200 stores where I really want to drive up sales. I can run a campaign in a set of zip codes with a reasonable amount of spend to really build up my brand within those zip codes. These are easy things for you to be able to include in all of that. I think in the same way if you're a CPG brand and you're running ads on Meta to build up your brand, you'd want to be able to do the same for retail. 


The other thing that I would say is that we're seeing, from the more sophisticated brands that we're working with, develop creative for that specific retail channel. If you're available in a very specific channel, like one of the brands we work with, which is only available in New York bodegas, develop creative for that specific retail channel. We work with a bunch of New York influencers to have them walk into the stores, and create content to turn into creative. These creatives are [also] going to work well for Meta. They are also going to work well for television. Since they are geo-targeted, it is really easy to spend a couple of hundred dollars per day to support the launch.

The world where a brand had to be nationwide to do TV is gone. These brands had to shoot these million-dollar television commercials with huge licensing budgets. When you look at who is performing well in terms of like zip codes and DMAs with your Meta campaign as a CPG brand, you're going to find that a similar audience is probably sitting on their couch watching streaming, and there is an opportunity to hit them with a high-quality creative, and then what we see with the brands is that television halo effect. Both the brand recall of putting a 30-second television commercial in front of that consumer, but also the next time they are, whether it's in a retail location, or they are in the purchasing mindset, that television commercial, we've seen it for quite a few of our customers, has a pretty significant impact on their overall conversion rates. 

NSP: When you talked about your career, one of the interesting things was that you've been at the forefront of multiple platform shifts with mobile ads, CTV, and the AI world. I think one of the interesting parallels here is what we're seeing in the retail media space. As you mentioned, it's very much exploding. Walmart, I think, last quarter reported something around the lines of like a third of their operating profit is coming from retail media. Also, Target is partnering with ChatGPT to get it integrated into their media network. And there's so much more there that is going to be possible. Where do you see the retail media world headed, and what do you feel like is misunderstood about how that is happening right now? 

KW: Much of my information around retail media comes from working at Moloco, they have a retail media business where they work on the supply side with a lot of these retailers to help them build their retail media platform. I would say [there are] two things that I think are exciting about the retail media, and then at the same time, a challenge is that you can get in front of very, very targeted consumers. If I am already on Target or Walmart’s website, it's not like I'm thinking about buying something. I am in buying mode. In some cases, maybe I did just buy something, and I'm kind of like in lookie-loo mode for something else. On the pro side, being able to reach a consumer when they're in that buy-now mode, is super exciting about retail media networks in general. 

Obviously, there's a slew of different types of media retail media networks, from everything from in-store television ads running physically in those locations, all the way to the obvious stuff that we've seen for a long time, which is like sponsored listings inside of Amazon. It gives brands that really know their consumer, the opportunity to get in front of them. That said, it's like any other paid channel where you have to decide whether this person is already typing in my brand name and I'm just paying to have the first listing be mine versus someone else's. I think that there is always that guess and check that you want to have if you're going through this process. That is probably the downside of retail media, that these purchases and transactions were probably already going to happen. 

I think as an up-and-coming startup brand, you do have the opportunity to, when someone types in something, be able to get in front of them when they're in that buy now mode. I think what I'm excited about is on the creative side, the ability for brands to now tell a more compelling story and be able to, in a 30-second television commercial or their best-performing Meta ad. To be able to, on these retail media platforms, potentially have a much better creative that drives performance. I think we're all bored with these simple text-based retail media ads or the text-based creatives with a static image. I think we're definitely at the point where the creative needs to be matching the revenue that is coming through these platforms. That's where I think when we look at the future of upscale, we do see brands using us for CTV, YouTube, and retail media creatives. 

NSP: One of the themes I've been seeing frequently is efficient spend across all different types of media ecosystems. People are really focusing on lowering the customer acquisition costs, and to your point, making sure that when they're spending money on an ad, that's actually an incremental sale. From what you're seeing across all the different brands you work with, how have people been able to scale their marketing spend efficiently? Are there any trends you're seeing from those brands that are able to separate themselves as being able to really get that efficient spend? 

KW: The biggest trend just in the last two years that I've seen is the adoption of incrementality. Whether that is incrementality in the sense of, I'm gonna turn something on or turn it off [to test if it works]. I've seen a lot of brands run the 14-day branded search, pause, and unpause. To your point, you need to measure it. You have the last click measurement from a Triple Whale or a Northbeam. You have in-platform measurement where the YouTubes and the Googles and the Metas of the world are telling you, they drove $5 in sales for every $1 you spent. How much do you believe that? The final last boss that we see is incrementality. Whether it's House or Work Magic, a lot of the brands that we work with have a vendor for this, where they can do geo-based incrementality, and it's super easy to do. 


In the day of Claude Code, you, as a brand, can also work with Claude to structure some of your own incrementality tests, whether that is geo-based, user-based, or time-based. In the same way that a brand is focusing on, how do I increase conversion rate optimization, how do I optimize for LLMs, you have to be in a testing framework. I think that a lot of the brands that we see have some form of incrementality that they're doing in order to figure that out. 

Then, when you get to the level, you are spending tens of millions on advertising is the media mix modeling. It's obviously not precise. [However,] at the end of the day, what you want to be as a brand is just to have a good sense of whether this channel is performing for me in an absolute way or not? Do I feel comfortable if I put a dollar in? Am I getting the brand awareness, or am I getting the direct performance that I would expect to see from that dollar and spend? 

There is the relative question of whether I put one more dollar into Meta or if I should just test a new channel. I would say, from what I'm seeing on LinkedIn and Twitter, and talking to the brands, a lot of brands are now focusing on this metric around net new consumers. It is one thing to be showing the same ads, the same consumers that you're talking to all the time. [Consumers who are] already on your SMS or email list. [You want to avoid] saturating that. The other aspect, as brands scale in revenue, is that I see more and more is that they think about how to reach new consumers who have never heard of my brand before and get them excited about what we're selling. 


NSP: I know we're almost up on time, and thank you so much for sharing everything today, Kevin. The last question I always like to end things with is, is retail dead or alive? 
And why do you think that? 

KW: Retail is very much alive. I think that the entire world is moving towards more in-person experiences. I was in Target this weekend. We love going to Target to look at products, and there is a different variety of stuff that's there versus Trader Joe's versus other places. The benefit of living in New York is the density of retail that is available. In looking at the acquisition market, like Shein acquiring Everlane, the brands that were first to market saying word D2C have only proven that the best way to scale a brand is to meet the consumer where they are. 
There might be 20% of consumers who only buy on Amazon. Okay, that's a fifth of the population. There are another 20% or 30% of consumers who will buy from your website directly. Where's the other half of the population going to find and access your brand? 

I look at Sean Frank over at Ridge, and he's a huge believer that he needs to meet the customer where they consume products. He's in Best Buy, and I have seen Ridge products in other places. I think at the end of the day, trying to find a way to meet the consumer where they are is the future of retail. 
It'll be a combination of what I'm happy to buy from a Shopify store, or if I can get access to the brand via retail, that's probably my preferred way to buy anything apparel-wise. I think at the end of the day, retail is very, very much alive. The most sophisticated brands are turning retail into an opportunity. Whether it is doing pop-ups, or I look at a brand like Bandit, who does these drops around marathons, these are special events, and they're using retail as a way to be special.

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