From Instagram To Deets: Creating A Seamless Video Commerce Experience With Doug Weiss

TLEP 79 | User Experience


Welcome to this episode of our podcast, where we sit down with industry leader Doug Weiss to discuss his extensive experience in both commerce and creators. Doug is a seasoned entrepreneur and former CEO of Deets, the groundbreaking platform that revolutionized the way we discover new restaurants.


In this episode, we dive deep into Doug’s experience in the tech industry, specifically his role in creating the Creator Commerce and Commerce Platform Partnerships teams at Instagram. Doug shares how Facebook and Instagram recognized the need to push for commerce and how he helped lead several initiatives within the company to drive this vision forward.


As head of Creator Commerce, Doug developed a tailored approach to support creators on their ecommerce journey by simplifying the technology and providing education on how to sell. He discusses the challenges that creators face in monetizing their content and how his team worked to address these issues.


During our conversation, Doug Weiss also shared his perspective on why video has not yet taken off in the US and what needs to be done to capitalize on the opportunity. He believes that the US has been slow to adopt video as a primary mode of communication due to a lack of commerce driven content. However, he sees tremendous potential in the use of video for commerce and believes that the industry is finally catching up to the demand. Doug discusses the importance of creating a seamless user experience, providing value to both creators and consumers, and developing new content that will drive engagement and retention. He is optimistic about the future of video in the US and believes that it will play a crucial role in the growth and success of the ecommerce industry.


Whether you’re an aspiring entrepreneur, a seasoned industry professional, or just curious about the future of commerce and creators, this episode is a must-listen. Join us as we learn from one of the most innovative and influential voices in the creator & tech world.


About eStreamly: eStreamly is a Livestream & video shopping SaaS. Your video content is shoppable on your site, a blog, email, SMS, a 3rd party webpage, and now also shoppable on social media too (Instagram, Facebook, Youtube)! It’s your data, your ecommerce. Each video become an extension of your ecommerce with in video checkout. 


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From Instagram To Deets: Creating A Seamless User Experience With Doug Weiss

We have a special guest, Doug Weiss. This is a gentleman that I met at Shoptalk. We were engaging through the show, and I end up having a fun conversation and said, “This person is knowledgeable about the creator economy, live commerce, and video commerce.” I dig in to learn that he was the first Head of the Creator Commerce for Instagram. I’m so delighted about this conversation. This is going to be a fun conversation digging into what went in the Head of Instagram and Facebook at the time when they thought about going live shopping and see the trend in what was going on in China and say, “How do we bring that to the US?” I am so excited about this.

Before we jump in, a quick update on eStreamly. It’s a streaming, livestream, and video commerce platform as you know. We have released a new feature on the analytics side related to user behaviors to give a more understanding of what the user is doing on the video. We are doing that at a very granular level, giving you, as the person using the live, more understanding of what the customer is doing, where are they doing, and what are they watching. I’m pretty excited about this feature.

Let’s dive in. Doug Weiss is an industry leader. He started both the Creator Commerce and the Commerce Platforms Partnership team on Instagram. He is the former CEO of Deets, the only platform that helps you discover restaurants through your own dining preferences. That sounds interesting. When I think about finding a restaurant, I’m always looking at what my restaurant can do and if they know my preference, then they will suggest me good things. I love that idea. Those trusted friends and sophisticated machine learning are everywhere nowadays.

He started his career at McKinsey & Company. He’s focusing largely on digital and marketing projects. He is advising a portfolio of companies, focusing on developing the next generation of commerce experience. Perfect timing for us, because that’s where we are with this show, which is around discovering new customer experience and shopping experience for your customer. I’m excited to have you. How are you doing, Doug?

I’m doing great. I appreciate the opportunity to talk about my own experience and speak about what I consider to be one of the most interesting things happening in technology, which is how we build the next generation of how people shop. As someone who loves shopping my entire life, as people have moved to the mobile device so far, technology has lagged. Being able to talk about what are those new things that can create a delightful experience for both shoppers and brands is something I’m always happy to talk about.

If we look back at your career, you have lived through that from McKinsey. It’s interesting because you started on Facebook originally, and you were more related as a product growth manager, mostly around ads, and you stay there in that for four years. After those four years, you started from a partnership perspective with Instagram and Facebook shop, but you were focusing mostly on the technology.

I had started my career and got lucky that I joined Facebook as the ads business was taking off. It was already a very large company, but how that company was going to monetize was an open question. Through the four years that I was working on the ads side of the house, got to see one of the most impressive marketing platforms ever get to be built.

The thing that became quite obvious is that all of the things that made the platform a good advertising platform also made it a good opportunity for commerce. You had every brand in the world on the platform. Our most recent earnings showed that 1 in 2 people globally, and more than 2/3 of people in the US, are on our platform almost every day. You had this opportunity to make it possible for these brands who are looking for different ways to connect with consumers and not only drive awareness of their products but drive sales. It was an interesting next opportunity to pursue across the company.

TLEP 79 | User Experience
User Experience: One in two people globally, or more than two thirds of the US population, are on Facebook almost everyday. This is an opportunity for brands looking for different ways to connect with consumers.


The first thing that I worked on was building that foundational infrastructure and foundational technology. The reality is nothing can happen unless you have that ability to make transactions happen. My first role was working. Instead of Facebook or Instagram building its own commerce technology stack brands would have to onboard how we work with the existing technology players that power websites around the world like Shopify, BigCommerce, Feedonomics, and Salesforce Commerce Cloud. How do we work with those companies to make it easy that if you are on one of those technology stacks, not only can you sell through your website, but now, increasingly, you could sell through Facebook and Instagram as well?

That’s a vision that I can share because that’s how we are thinking through this. Interestingly, it’s not the similar vision that every platform has. Not to name anyone here, but there are other people that are thinking about doing all in-house. Already, we can see a big fundamental difference from other platforms out there where you want this experience where you say, “Let’s leverage what’s existing, connecting those platforms, and then see how it goes.” This is a topic that I will want to come back to. Before I go there, I wonder how that came around in 2021. You become the first Head of Creator Commerce. First of all, define to us what creator commerce is. How did that come around?

Creator Commerce across both Instagram and Facebook was this idea that in addition to all of the companies that are at their core, companies that sell products, all of your major brands, whether it be Nike or major retailers like Walmart. Increasingly and especially on social platforms, you have all of these other entities that are driving a lot of shopping behavior and commerce. Whether it be celebrities, whether it be influencers, whether it be sports teams, whether it be music festivals, you have all these entities that have these massive communities on our platform. Our team was focused on helping our product team build products for these audiences and then helping drive the adoption of those products that we were building to help drive shopping on the platform.

One of the things that we’re seeing across the industry is the way that people are discovering products and are deciding how to buy products, it’s no longer commercials and magazines, but it’s the Kim Kardashians, the Reese Witherspoons, it’s The Rock. Increasingly, when they have a piece of product in one of their pieces of content on the platform, that is the thing that moves the needle for sales more than anything.

Our team was focused on how do we build products, educate creators, and then get creators to use these products in the most efficient and effective way. In many ways, the team not existing until 2021 should have been built 5 or 6 years prior. This is the thing that makes Instagram and Facebook so interesting as a platform.

We love the content that Nike provides and creates, but it’s much more interesting to see what Serena Williams is doing than Nike Corporate. Harnessing the power of all of these people and entities that have built these very engaged communities on our platform, how do we then take these communities, and not only make them fans of a creator but help that creator sell any variety of products, either of their own brands or brands that they might be partnering with?

We had Joe Gagliese, the CEO of Viral Nation, that came on the show. He was mentioning the power of a creator and how it can drive sales, engage the audience, and his vision about what that could bring. I wonder in that specific context. In the beginning, you were in the ad space, moved to do a lot of things around the technology, and then moved toward the creator.

Can you give us an insight at that specific moment when Facebook and Instagram were like, “We need to embrace this in a stronger way,” and that’s why they created the position? Were they separating, “How do we involve brands and thrive with brands versus the creator?” Did you have different groups? If so, what were the main big difference you see whether mostly from how you engage the creator, like as an individual, or was it around features and things like that that were different?

Honestly, it was both. Let’s start with the product side first because it is the core of how you think of everything. The reality is if you’re Kim Kardashian and you have Kim Kardashian cosmetics, you may be driving hundreds of millions or even billions of dollars of sales. The thing that is always so surprising for people is that these teams are very small, often not traditional brand backgrounds, and looking for products that don’t have necessarily all of the nuances and bells and whistles, but want to get the product to the audience and be able to connect with the audience in this unique shoppable way.

Thriving sales teams are usually ran by small teams who lack traditional brand backgrounds. They just want to get the products to the market and connect with the audience in a unique shoppable way. Click To Tweet

A lot of the things that, for instance, bigger brands might be requesting in terms of multiple ways of showcasing products, multiple views, different types of insights, different skews that can be prioritized, one versus the other, all of that complexity was seen as overhead as we thought about creators and the brands that they were working with. We needed to work to streamline the product and make it easy to use because, instead of tens or hundreds of people that might be against an eCommerce business, most of these creative brands had 1 to 2 people that were running anything. Anything that was complicated got in the way.

The other thing that we focused on was a lot more of the two-way conversation and community-based forms of commerce that creators can tap into better than anyone else. People who are fans of whether it be an athlete or a musician, their engagement, the amount of conversation and community that they feel around this person, is so much stronger than what you usually see with brands.

Things around live shopping and things around the ability to do potentially shout-outs as someone might make a purchase and recognize people who made a purchase from a creator, some of these two-way conversation community-based capabilities became much more important. We prioritized them as we thought about the development of products for this subset of entities that were selling on our platform.

Beyond product, how you brought it to creators was also very different where because of the smaller team, because of a desire to keep things easy and intuitive, making sure that you educated the teams well and that they understand the products and the upside of not only on a revenue basis but the way it would help them connect with their community. We did a lot more webinars in-person or over-video types of engagements while brands usually wanted things in decks and websites.

Sales teams must know the upside of their products not only on a revenue basis but also how it would help them connect with their community. Click To Tweet

It often needed not to be shared with one person, but potentially with entire teams of people. This is why we created this team. The way we were working with brands wouldn’t have worked if we had tried the same tactics with creators. We needed to have a team that was in the mindset of a creator both in terms of what were the products that need to be built, as well as the ways that we needed to bring those products to market.

Hearing you, probably the biggest insight that I will get so far is when I talk to brands, that notion of community is always something that is not emphasized enough. Yet you being in the social sphere, you understand that the number one thing that you need to do is to drive and accelerate that community because that’s what’s going to drive sales.

Even at your level as big as Facebook and Instagram can be, the emphasis was not on the community when you were approaching the brand while it was on the creator’s side. For the brand and retailer, community is something that we all need to pay attention to because who is watching email anymore? Email is still the number one driver of sales for most eCommerce, but at some point, people are going to be crowded with emails. We have the ChatGPT that’s going to write soon our emails instead of us. We are going to be more and more looking at emails with no interest and desire to read them, or the bot is going to read them for us.

How do you reach me? How do I reach you? How do we reach your audience? The community is going to be the biggest place. I wonder what you think about that because you are looking at the forefront of commerce. Do you think brands pay enough attention to that? Is there enough money invested in this space? What’s your point of view there?

One way that I always like to think about things is Nike has, for instance, 289 million followers on Instagram. These are people who like the brand so much that they are proactively following you to try to understand what products you’re launching and to hear from you. If you’re not actively connecting with them and creating not only content that you might have in a magazine, but this thing that fosters this sense of community, you’re leaving that audience who is so primed to be some of your best customers on the table and you’re wasting it.

It’s this idea of harnessing these people and these entities. This is where the creator-brand intersection becomes so important. In that pool, for instance, for Nike of almost 300 million, you probably have 100,000 that are constantly potentially tagging your products, creating content, and showcasing your brand in amazing ways.

There’s been a lot of growth in creator marketing over the last few years, but we’re just getting started because that is the type of thing that’s resonating most with consumers. Brands that aren’t leaning into the creators, the people who are their advocates, and the people who they’re representatives with these massive communities that they’ve built online are wasting a lot of opportunity.

As it becomes harder to reach people due to changes in iOS and the inability to target users as well as you might have been able to years ago on digital platforms and people increasingly ignoring email, using creators can be a very effective way to not only connect to your own community but also to connect to the creator’s community and take advantage of that influence in that community that you’ve built.

TLEP 79 | User Experience
User Experience: As it becomes harder to reach people due to iOS changes, the inability to target users, and people increasingly ignoring email, using creators is an effective way to connect to your community.


That’s where my head’s at with that. It’s true. We have to recognize that community is also very difficult to manage. It requires a lot of effort and time. That’s probably also one of the reasons brands now are not completely investing yet but it’s something that creators know to do very well. They engage their community daily. Maybe in your own network, you have a creator that could certainly manage your community on your behalf.

It reminded me, we had a guest at the beginning of the show. His name is Brian Fanzo. He’s on the Web3 side. He kept talking about how in the Web3 space, the community manager are people that are fans of that NFT or that product that you have, and end up growing through the ranks. At some point, you’re like, “I need to make that person a community manager.”

That could be done that way. They live and breathe your brand. They love what you’re doing every day. Empower them. As you will empower your team in your company, empower your customer to become your best ambassador. I love that on the community side. There’s so much opportunity for the future. In my view, it’s going to keep on like that.

We all have heard the news that Facebook and Instagram were dropping that whole commerce initiative. In some way, we had the same news running around TikTok. TikTok played the game. They’d never responded, but they were doubling down on the side. In some way, we know that Facebook and Instagram have pulled because, at least from the app perspective, we don’t see those things anymore. Do you think it’s because they are reevaluating the strategy to do it in a different way? Do you think that is not the place where they want to play on?

There is this meme that exists in the industry that Facebook and Instagram are pulling back from commerce. The reality is that’s not true. As you said, it’s very much of those two scenarios, the first where it’s being positioned and built in a pretty different way. If you look at how commerce was built initially, it was built as a new initiative, as something that was a standalone product. Even on Instagram, you had a separate tab that was different from the rest of the experience. One of the things the company realized is that one of the things that was a beauty of commerce on Instagram before, for instance, a separate tab was built, is that people were doing it in all different ways that they might use the platform.

When we tried to get them to be like, “Instead of doing shopping in Feed, Stories, or Reels, we want you to be shopping in our Shop tab.” There was this realization that the thing that works most effectively is to leverage this great platform that is the core of what the platform is. The Feed is the thing that brings people back to the app time and time again. It’s the messaging capabilities that bring the people back to the app time and time again. Instead of trying to build something from scratch, how do we integrate commerce into all of these different areas throughout the app that has resonated so much with consumers?

TLEP 79 | User Experience
User Experience: Facebook and Instagram feed and their messaging capabilities bring people back to app time and time again. There is no need to build something from scratch. Integrating commerce into these different areas is enough.


Even though there have been some of these seemingly very public and obvious changes to that almost diminishing commerce, the thing that’s growing the most is the eCommerce activity in the app over anything else. In 2022, you saw a dip as some of the targeting capabilities became much more difficult. In 2023, you’re seeing this recovery. Again, it’s because the way that the platforms are thinking about commerce is integrating it into that overall experience. It’s less of a step back and it’s more of an evolution. The reality is the things that made Instagram and Facebook excited to be investing in commerce years ago are still very true.

I honestly went through this myself. I needed a new pair of jeans. I didn’t even know where to start. There’s not a place I can go where it’s like, “You know what kind of jeans I like. You know what brands I like. You know what size I am. Help me find what I need to find.” That opportunity still very much exists. Instead of trying to create something separate that would address it, it’s figuring out, “How do we weave in the experience into what commerce is like and bring in some of those commerce and shopping capabilities to meet the consumer where they are?”

I love it when you say you wanted this pair of jeans. You didn’t go to Google and tap jeans. If you wanted to have a personal experience, you wanted to see through content. I do believe that in our generation, we are moving toward a content-based behavior whereas our parents and grandparents were more on the search-based behavior. We want to see the content. Like the pair of jeans, I want to see them being worn. I want my favorite creator to talk about it. I want someone I trust and know who talks about it and then being able to shop from that.

It’s interesting how people are changing. I’d love to de-zoom a little bit about this whole conversation instead of focusing specifically on Insta and Facebook. It sounds like you’re bullish on video commerce still, especially for the US. Still, it has not kicked in. People are still talking about it. You will see 10 articles saying, “It’s coming,” and then you have 4 articles saying, “It’s dead. It’s never going to be there.” We’re still in this troubled water where people are trying to find themselves. What’s your point of view on that story?

I have built part of my career on this. I’m probably somewhat biased. I still very strongly believe that video commerce will eventually be a real thing. The thing that has been the blocker to date, and this is going to continue to be true until we solve this problem as an industry, is the lack of video commerce content that exists. If you go into Instagram, you don’t come across video content that’s shoppable very often.

There’s an article in the Times about the thing that happened in China. They have democratized access to the creation of video content to the point where it’s the other end of the extreme, where you have video, live shopping, schools, trainings, and whatnot and you have millions of people who are trying to make it as a live shopping creator. I don’t know if we need that extent. The reality is that live shopping is a different experience from how people are used to shopping. Even if it’s something that they would prefer eventually, they need to get used to it. The only way you get used to it is by being exposed to it over and over again.

We used to work with brands all the time where there are two things. One is it is a skill. It’s not necessarily an impossible skill to learn, but the first time someone does something, it often isn’t great high-quality content. There is this knowing how to connect with the audience, knowing how to show the product, knowing how to be able to show the product and do the conversation at the same time. That is something that the first couple of times is not going to be a success.

Brands sometimes try it, don’t see success, and then give up. You see a lot of brands not doing nearly enough. On the other hand, you don’t necessarily have them tapping into the people who should be doing this in the first place, which are creators. This is what creators do well, creating content that resonates with people.

As the times that we saw live shopping or video commerce be most successful would be when you are tapping into these individuals and people who know how to talk to an audience, know how to use this tool, know how to use this technology, and are able to resonate. Since you don’t have brands enabling creators to create it, you don’t have that much content overall. Outside of a couple of pockets here and there, you don’t have enough content. The consumer doesn’t know how to shop through video commerce.

Live shopping or video commerce are most successful when they tap into people who know how to talk to an audience and resonate with the market using technology. Click To Tweet

Underpinning all of this, it took a long time for the platforms to build out the payment infrastructure and all of the backend to be able to facilitate a seamless experience, which is critical for this to be successful. A lot of the platforms have done a much better job on that. It’s about this creation of content that is going to be the thing that unlocks this very massive opportunity.

There are three things that resonate with me. The first one is this notion of doing it a couple of times and then dropping. In your perspective, most people are doing that because they are maybe doing it, and then, because it’s the first time, they don’t know how to do it and it’s poor content that leads to failure. It’s maybe a lack of persistence and consistency. 1 in 2 podcasts launched doesn’t go over the number 8 episode. When you think through that, you can’t build an audience and you can’t activate your audience by doing 1 or 2 shows, or you have to spend a lot of money to make it happen.

The other thing that I enjoyed hearing is this notion that creators know how to do this. They are skilled. The little caveat I will say for that, where we personally work with creators, not only do we look for people that sell because it’s a skill but also people that know how to engage live. Not every creator is created equal. Some are good on Instagram for pictures and short-form videos but when it comes to livestream, not everyone is good on the livestream.

The best example is if you go to YouTube or Twitch, you’ll see different types of creators from a content perspective. If you extract the content and look at how they engage the audience, a livestream creator has this way of connecting with the audience in a very meaningful way. It’s certainly those things like consistency and the creator are going to make it happen. Talking about content, in your point of view, what makes for good-quality content? What’s shoppable content? I understand that you say, “We need to give creators more power and empower them,” but is it only on the creator’s side or does the industry need an infrastructure to help us with this?

One of the biggest things that is great about video content is this idea that showcases the product. The thing that’s different about video versus still images is the fact that you get to see the product in action. This is true for fashion. This is true for beauty, but things that showcase how the product can be used so that the real use of the product makes a ton of sense.

Video content truly showcases a product in action. This cannot be fully attained by using still images. Click To Tweet

The other thing is this. You have someone using that two-way conversation, where it’s not someone showcasing a product, but where you have the ability to ask a question, get input, and make sure that the things that may not be on the top of a creator or a brand’s mind but are on the top of the mind of a consumer? You are able to have those questions answered and almost like the experience that you might have in store, have this ability to get the full information that you need to make a purchase.

I have one last question before we wrap up this episode. It’s been a fascinating conversation. As the former CEO of Deets, you can speak about the importance of using sophisticated machine learning and creating personalized experiences for the consumer. How do you think the brand can utilize this technology to understand the video commerce strategy? Do you think there is a path using AI machine learning based on your experience of everything you know from a technology perspective, from a creative perspective, from a video commerce perspective, and then from an AI perspective? You’re the perfect guest to ask that question. Where is that special fit, if there is any?

You need to start with what you’re trying to solve and then work backwards to see what technology can do that. The thing that people are increasingly looking for is video commerce pieces of content that are relevant and resonate with them. With machine learning, you can have a much better understanding of what are those questions that your audiences are asking.

From ratings and reviews, you’re able to see, “Are people asking about size? Are they asking about fit? Are they asking about the feel of the product?” From there, you can make sure you can create assets that showcase the things that are most important, while potentially by utilizing a portfolio of creators, you can map assets created by certain specific creators to audiences that resonate most to them.

There’s this question around who your audience is and what is the right type of person that can resonate with that audience. You can use a lot of machine learning and AI to be able to do what Instagram has been doing for years now, which is mapping the right person with the right creator and product to make it as likely as possible that you’re going to be setting yourself up for success.

The most resonant piece of video commerce content for me might be very different than what it would be for you, which might be very different from someone who is a generation younger, a generation older, different gender, or from a different part of the world. Being able to use machine learning and AI to be able to map the things that are important and make map content to those different characteristics can make sure that you’re getting the right content around the right product to the right person at the right time.

TLEP 79 | User Experience
User Experience: The most resonant piece of video commerce content might be different for every individual or generation. Use machine learning to make the right content around the right product for the right person.


I love that. It’s much around the recommendation and the content distribution, but at the same time, using those solutions to understand where are the pain points of the customer and then trying to surface that as much as possible. Machine learning is great when you have a huge data set. If you are an entrepreneur, you are launching, and you have 10 to 20 products, it may work for you to go over your own review, go over what customers ask you every day, and then from that standpoint, think about what content you could create to answer those questions. You come back to those same things.

That’s how business and marketing, in some way, should be done. What are the questions the customer is asking and what content can I create to answer those questions? If you have the ability to make that shoppable, you’re removing the friction. You’re going to have a much stronger path to purchase. It’s been a fascinating conversation. Thank you, Doug, for taking the time. Where can the audience follow you or ask you a question if they want to learn more about you? What can they do?

As someone who works with creators every day, I’ve become very aware of the importance of these different platforms. feel free to reach out over LinkedIn at Doug Weiss, but also on my Instagram, @DouggieQuest. It’s the fun, social, and personal side of my life. I love talking about this. We’re in the midst of exciting changes that are happening industry-wide. I think we’re at the beginning of it. I’m always eager to connect with other people who are interested in these topics and to talk and learn more.

You will have the ability to rate this episode and this show altogether. You can share it with your friend, your favorite content creator, or your favorite retailers. This is always something that we are doing for you, hoping that we can provide more and more value so you can learn and grow your video commerce strategy. We had some amazing guests coming up on the show. Doug is one of them. We had Joe Gagliese. We had Jim Fuhs and so many of those great talents in the live shopping space. Please feel free to watch out, like, and share, follow us, and until the next episode. Bye for now.

Thanks so much.


Important Links

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