As part of the second edition of our “Meet the Leadership” series, we’re excited to introduce Andee Olson, Chief Operating Officer at Obsess. We asked Andee to share highlights from her professional journey, what led her to Obsess, advice on impactful leadership, the role of gamification in commerce today and her thoughts on the future of engagement in virtual experiences. Here’s what she had to say:
Q. You’ve had an impressive career journey with roles at companies like Vogue and Bumble. Can you walk us through that path and what ultimately led you to Obsess?
AO: When I look back at my career journey, I’m reminded of a campaign we did at Bumble called “One Connection.” The whole idea behind the campaign was that it only takes one person to believe in you, see your potential, or encourage you to take a chance. This has held true for every opportunity I’ve had throughout my career.
A friend recommended me for an internship at Vogue, which ultimately turned into a full-time role. I worked there for many years and made connections that led me to every single job I’ve had since. I worked with people who later recommended me for roles at Bumble and hired me at Code and Theory, and I feel very fortunate for that.
I also worked with our current founder and CEO, Neha Singh, at Vogue, where she was leading product at the time. I was working in a more operational and strategy role, given my engineering background, and she was the one who encouraged me to explore product management. I had never heard of product management before, but it turned out I was already operating in that capacity. I took proper training and product management has been something I’ve applied in every role since. After we both left Vogue, I told Neha to keep me in mind if anything interesting came up in the future, and I always said I would follow her anywhere. And sure enough, she did! I’m so grateful that Neha was one of my “one connections”—her encouragement brought me many career opportunities and ultimately led me to where I am today.
Q. For those starting their careers and aspiring to leadership positions, what are some qualities or lessons you learned along the way?
AO: I’ve had amazing role models and mentors—people I look up to and still go to with questions. So, I definitely want to give back what I’ve been given. Everyone has a different leadership style and what I’ve found works best for me is supporting the team, leading with empathy and, of course, sometimes a dose of tough love goes a long way. I don’t ask of my team anything I wouldn’t do myself. I feel so lucky to manage such a hardworking group of people. They are driven, they are creative and they always bring their best to the table, which makes my job a lot easier. I’m able to set higher expectations because of it. The way I see my role is to support them the best I can. Ultimately, their success is my success, which is the company’s success. I’m here to be my team’s cheerleader for life—I want to be able to support them even after Obsess. I still keep in touch with so many of my previous coworkers.
For anyone aspiring to be a leader, you have to find what works for you when it comes to leadership style. A lot of the time, a leadership style may work for you, but it might not work for the people you’re managing—this is something I’ve learned along the way too. It’s about finding that balance: start with a foundation and evolve based on your team’s needs. You know, my dad has always been someone I’ve gone to for advice and looked up to for leadership guidance too. It was really interesting when, a few years ago, he came to me asking for my advice on something—tables can turn! I always tell everyone on my team that I’ll probably be working for them one day, and I believe that wholeheartedly because they’re all so smart and driven.
Q: On to your current role and the evolving virtual landscape—now, more than ever, we’re seeing the fusion of online commerce and gamification. Can you tell us more about the role Obsess is playing in this shift?
AO: Absolutely! I’m very excited about this combination, mostly because it’s something I’ve talked about since my time at Vogue and my agency days—the opportunity to mix commerce and content. There are multiple ways to shop, and no shopper fits into just one category. In fact, most fit into multiple categories. The two most common are: “utility-driven,” where a shopper knows exactly what they want to buy, and “exploratory,” where shoppers want to search, learn more and get inspired. Content helps you do exactly that.
Gamification is a continuation of this conversation. You’re adding an engagement layer on top of everything, and you’re making the exploration aspect fun. At the end of the day, shopping should be fun, right? When you’re looking for something, you want to feel inspired and you also want to enjoy the process. And while you’re doing that, you’re engaging with the brand. The more you understand what the brand is about, the more memories you’re making—and those memories will stick with you! You might not purchase at that exact moment, but you’re likely to purchase in the future because of the connection you’ve made with the brand.
When we look at our customers who have prioritized gamification in their virtual experiences, the results speak for themselves. Users are spending more time, clicking on more elements, returning more often and checking out with more products. Ultimately, you have to cater to this exploratory audience. If not, your brand will miss out on a huge opportunity. It’s the natural extension of what’s been happening for years—first with 2D content, then with Obsess’ 3D content, and now taking it one step further with gamification.
Q. On the topic of gamification, over the past year, Obsess has designed and developed branded experiences for Roblox. With physical commerce now part of the platform’s roadmap, what is your recommendation for brands?
AO: I could not recommend Roblox more for brands, especially those looking to target younger audiences. While Roblox is known as a gaming platform that appeals to young children, it’s increasingly popular with the 18-34 age group, which is what’s enticing brands. According to the latest numbers, Roblox has nearly 90 million monthly active users who are spending over two and a half hours a day on average—more than on social media platforms. So, this isn’t just an incredible audience in terms of size, but it’s also a highly engaged audience.
So if I’m a brand, I’m thinking: how do I reach this high-value audience? One way is to go to a platform where that audience already exists—and this audience definitely exists on Roblox. What’s so unique about Roblox is that you’re not only reaching this massive audience, but you can also completely customize the experience to make it truly unique to your brand. This allows you to educate consumers about your brand, showcase what you have to offer and even incorporate your brand’s core values—all through a fun and engaging experience.
Now, with the recently announced Shopify integration, brands have the ability to convert these users into paying customers. If brands aren’t paying attention to this yet, they absolutely should be, because many are—and you don’t want to be left behind with this audience. I think we’ll see a lot of brands take advantage of this partnership next year, especially since some have already started making a splash in the space. What’s exciting for us at Obsess is that we’re able to bring our learnings from virtual stores and experiences into Roblox—how to create an experience that aligns with your brand, educates and engages your consumers, and ultimately converts them into shoppers.
Q: What are some other use cases for 3D technology do you see in the next few years?
AO: There are a couple of things that I’m excited about, one being B2B solutions. I remember working on case studies in college and thinking about the area of the B2B solutions, which have traditionally been very operational and process-driven. Not a lot of technology was going into that space. In my agency job, I worked with a lot of companies to help with their B2B solutions. Now, when I think about it, there’s so much 3D technology can do for sales enablement, learning tools and more within the B2B industry. When I think about the potential, the work we could do to help businesses reach consumers, improve their processes and efficiencies and make what they do so much more scalable—and of course, engaging—is incredibly exciting.
Another area is real estate. As someone who’s always keeping an eye on real estate—constantly exploring properties I’d love to buy, and as someone who, when moving into a new home, creates old-school collages of furniture in Google Slides—I’m thrilled about the potential for immersive solutions in this industry. There are so many different aspects of real estate that could benefit from 3D solutions, from building and concepting to execution at both commercial and residential levels. Visualizing design, layouts, and materials all in 3D could completely transform the experience. I mean, the possibilities here are endless. From day one at Obsess, I’ve thought, these industries could really use a shake-up. Now, I finally feel the technology is in a place where we can truly offer something that’s both unique and beneficial to them as businesses.
Q: Lastly, where do you see immersive technology going in the next five years?
AO: When I think about how much has changed since I first started working at Obsess three and a half years ago to now—it’s been incredible and so impactful. In five years? I can’t even imagine, but there are some things I think we’ll start to see more of, and at scale.
First, immersive experiences that are personalized for you. Today, most experiences we create are driven by what the brand thinks you should be buying. What we’ll start to see more of are experiences driven by what you, as a user or shopper, want to buy. We’ve been doing this in some passive ways, but there’s so much room for evolution, and we’re actively working on it—a lot of it powered by AI.
AI, in turn, is another area that will begin to drive this industry and technology, making it more efficient and effective. I also don’t think this will necessarily take five years; we’ll start seeing this much sooner, but in five years, it will likely be happening at a much larger scale.
