Adam Mayer, SVP of Monetization at Chess.com. Chess.com is one of the most popular freemium platforms in the world, offering millions of users free access to an engaging online chess experience. But how do you encourage players to upgrade to a paid tier when the free version is already so compelling?

Adam, with his extensive background in revenue strategy and subscription growth, has played a critical role in designing and optimizing Chess.com’s premium offerings.

In this conversation, we’ll dive into the challenges and opportunities of building a successful paid tier within a thriving freemium ecosystem, how chess.com balances free and premium value, the strategies they’ve used to convert free users into loyal subscribers, and the key lessons Adam has learned from his experience leading revenue at a fast-growing digital platform.

If you’re interested in learning how to drive revenue without alienating your free user base, how to craft subscription tiers that meet diverse customer needs, and how to foster long-term loyalty in a competitive market, then you won’t want to miss this episode.

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Listen to the podcast here

How to Build a Strong Subscription Business While Maintaining a Compelling Free Tier with Chess.com CRO Adam Mayer

Adam, with his extensive background in revenue strategy and subscription growth, has played a critical role in designing and optimizing Chess.com’s premium offerings.

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Robbie Baxter: Adam, welcome to the show.

Adam Mayer: Hi, Robbie. Thanks for having me. I’m excited to be here.

Robbie Baxter: Yeah, I’m so thrilled to have you. You were actually a recommendation by a past guest (Babbel’s CRO and US CEO Julie Hansen), which is super fun to have. So I’m really glad we got your story and I’m really looking forward to it.

Adam Mayer: I’m excited. Hopefully a fun story to talk about.

Robbie Baxter: Let’s start. This is Subscription Stories. We have subscription practitioners and subscription experts. Tell us how you came to be a subscription practitioner, and expert.

Adam Mayer: I’ve been in media and technology for most of my 20-year career and about 10 to 15 years ago, I was at Time Warner Cable, which is obviously a subscription-based company. And one of my roles there was to launch and run the new smart home security space. Which was home security with thermostats, lights, and a lot of the stuff that we take for granted now. Remote, of course, and that was a subscription model.

That was my first kind of really running a subscription business. It was very different than what I’m doing today and then after that, I worked at WWE, the wrestling company. No, I was not a wrestler, despite my best attempts. But there I ran the business side of WWE Network, which was WWE’s subscription-based streaming service. It was basically Netflix with wrestling content. And, again, from the business side, I was responsible for acquiring, retaining, messaging, and marketing to subscribers. I spent four or five years there. It was amazing, great business. And then from there, I came to Chess.com, which again is primarily a subscription-based business model. And I’ve been here for now three and a half years. So it’s been a good 10 plus years. In the subscription space, which is a fun place to be in.

Robbie Baxter: Yeah. What made you go from WWE to Chess.com? You started it at a telco, you moved to a streamer, and then Chess.com. It feels like a big jump.

Adam Mayer: It’s from the wrestling ring to the chessboard, right? Everyone says that’s so different.

Robbie Baxter: They’re all games.

Adam Mayer: So of course there was a subscription business model that was a common thread through all of those so I had that understanding. And there are certainly things that apply to all of the businesses. It was all B2C, but what I really love about Chess.com and similar to WWE is there is a huge passion for the product. Whether it was wrestling or whether it’s the game of chess, people just really loved it. I felt very attached to it. There was an emotional tie to the product. And it’s just great working somewhere where you are providing a product or a service that your customers love. And again, whether it was watching screaming fans outside the wrestling ring or reading our forums on Chess.com about how much they love the game, either way, it’s just a great feeling and it’s exciting. Being able to market and provide a product with that type of passion and fan base. There are many similarities between the two.

Robbie Baxter: Now, I know you’re being funny, but you weren’t a wrestler.

Adam Mayer: I was not.

Robbie Baxter: But you are a chess player.

Adam Mayer: I play chess, yes. I am one of the worst chess players at Chess.com, although in my last three years, I’ve definitely gotten better.

Adam Mayer playing chess

But yes, I was a fan of wrestling, but I was not a wrestler and I was a casual chess player. And I think what happened specifically was in 2020 when I was still at WWE and starting to think about my next job, the pandemic occurred, which we all remember. The other big thing for chess was on Netflix. There was the show, The Queen’s Gambit. So I was at home with my wife and we were watching The Queen’s Gambit. And I was like, I used to play chess a lot. Maybe I should start playing again. So I Googled chess and sure enough, Chess.com was the first. listing on the page and I started playing and realized how much I loved the game because I used to play a lot when I was younger and then I realized how interesting the company would be potentially. I started a conversation with them and ended up here.

Robbie Baxter: So you reached out to them.

Adam Mayer: Yeah, it was actually an interesting experience. There was a job opening that was not the perfect fit for me, but I used that as an excuse to reach out to them. And I talked to Eric, the founder and CEO, and some other folks about that role. And frankly, they rejected me. I didn’t get the job, which wasn’t surprising, because it wasn’t the right fit for me exactly, given my background. But they said, “Hey, Adam, great chatting with you maybe in the future, there’ll be other roles. Talk to us again, three months from now.” So I was like, okay. So three months later, I reached out to them.

There wasn’t a new role and said, “Hey, I wanted to chat again. We spoke for another two or three weeks. Had great conversations, was very excited, and they rejected me again. So I was rejected for the second time. Again, it wasn’t for a specific role, but they were just saying, “Hey, not the right time. We don’t have anything right now for you.”

And then I guess three months later, or maybe even four months later, there was another role that was posted that wasn’t exactly my role, but pretty similar to what my role is today. And I remember talking to my wife and she was like, “Adam, don’t apply. You already got rejected twice. If they wanted you, they would have reached out.” And I said, yeah, but you know what? I hear you. And I don’t expect them to get back to me, but I said, it’s such great conversations with them. It seems like such an amazing company. So I reached out, and they shockingly got back to me and three weeks later I got the job. So it was a nine-month process of two rejections. And I guess I tricked them the third time.

Robbie Baxter: Yeah. There are a couple of really interesting points that I just want to tease out for our listeners. One of them is that senior-level roles sometimes take a while to find the right fit. Two, I think it’s really important for subscription pros to be reaching out to interesting subscription businesses, whether or not you’re specifically looking for a job at that moment for a few reasons.

One is to become familiar with different models, learn some best practices, and have peers who share some of the same challenges and opportunities that you do. And also because when you’re looking for a new job, it’s good to know the community.

Adam Mayer: Absolutely. That experience was a great learning experience for me about networking and being flexible. And I do think you alluded to this earlier, Robbie, the more junior in your career, at least in my experience, it’s much more set. Like I’m looking for that job and I need that role. As you get more senior, both you, the job seeker and I think the company that’s looking to fill a job tends to be more flexible. Like I was applying for one role and I ended up in a different role, but even the role that I ended up with what they posted, they changed a bit based on my qualifications. So whether it’s subscriptions or not, I do think that the more senior you get, be aware that it’s more fluid, conversations and networking, and being open to different paths is much more important than when you’re more junior and it’s okay, I’m looking for this specific associate role or this specific marketing manager role and it’s much more cookie cutter.

Robbie Baxter: Yeah. It’s such a great point. When you joined Chess.com after that third time was the charm. What was the situation there and what did they ask you to do?

Adam Mayer: Yeah, so Chess.com is a really interesting organization, and one of the reasons I was so attracted to it and one of the reasons I still love it so much is because while Chess.com is a for-profit company, it is unbelievably mission-driven. The mission of Chess.com is to grow the game of chess and to support the chess community. Erik Allebest, our CEO and founder has. obsessively focused on that mission since its founding almost 20 years ago. And there were three primary pillars beyond that mission.

One was to make the best product possible. Two was to serve the community as best as possible and make sure the community experience and the user experience is amazing. And three, make it the best place to work. What’s interesting is what was not on those top three is the business revenue. Now, the company to be clear, has always done well financially. It’s always been profitable. And maybe you could argue it’s because it hasn’t focused so much on that. That’s why they’ve done so well. Focus on the user, focus on the product, focus on your employees and revenue will come. So a long background to say that my role was a brand new role, which was head of monetization.

And the joke a little bit was that I’m the bad guy, right? I’m coming into this company that doesn’t want to focus on money and revenue, and I’m going to be the evil money guy. Now, obviously, that’s not how I’m viewed and not what I would want. So to answer your question in a long way, the mandate from Eric was, “Hey, look, as we are growing up, cause this was right after the pandemic and the company was getting much bigger, we need a bit more strategic thinking around our revenue and around revenue growth without sacrificing the mission.” And that’s really what my mandate was to come in, help us grow our revenue, help us be more strategic about the revenue, but honor the mission, which is to grow the game of chess and support our amazing community.

Focus on the user, focus on the product, focus on your employees and revenue will come. Share on X

Robbie Baxter: I’ve been working in subscriptions for a long time and something that I noticed is that a lot of subscription businesses, a disproportionate amount of subscription businesses are mission-driven because they have that forever transaction. We’re trying to improve the condition of our members in a particular area. And that’s an ongoing challenge that they face. They’re always trying to get better. They’re always trying to get healthier, or they always have challenges with productivity. It’s an ongoing problem and so a lot of these businesses are very focused. You can look at it in a positive way of we all are here to serve a mission that we believe in, you can also look at it more cynically and say, you don’t want to eat the golden goose, right?

If people are coming to you because they trust you, because they know you have their best interests at heart and you become too mercenary, you might destroy the business.

I think there are probably a lot of people listening who are experiencing this, whether they’re at a professional association, whether they’re at a gym. The goal of a gym, and there are some scathing articles every year in January about the cynicism behind many gym owners. We had the CEO of CrossFit, Eric Roza, on the show a couple of seasons ago, they’re there to help people be healthy. That’s the first goal. And the second goal is, and we need to be self-sustaining and maybe throw off some profit as well. A way that a lot of subscription businesses do that is by offering a lot of value for free. And I know Chess.com offers quite a lot of value for free.

Adam Mayer: Yes.

Robbie Baxter: How does the audience break out in terms of free and premium? And can you talk a little bit about the distinctions between the two?

Adam Mayer: Sure. So we have almost 200 million registrants on Chess.com. Now they’re not all active, but 200 million people since the founding to today, almost 200 million have signed up, given us their email, and set up an account.

There are about 35 million monthly active users, whether free or paid. Yeah, it’s a real business, a really exciting destination, and an amazing community. So we have three primary platforms, web, iOS, and Android. We’re a freemium business model. We have a free tier and a paid tier. We don’t get into specific numbers or we don’t share specific numbers of subscribers, but I’ll just say the vast majority of our users are on the free tier. And to your point about the mission, that’s wonderful. We want more people playing and loving and connecting with each other and with the game of chess and our free tier enables them to do that without paying a dime.

What you could do in our free tiers, you can play as much chess with whoever around the world with 200 million registrants. You just play a game and totally free. That will always be the case. We will always be letting you play for free.

Our premium features enable you to improve your game with some tools. So we have things like puzzles. We have things like lessons. We have something called game review, which basically analyzes your game. Now to be clear, and again, this gets to our mission. You can get puzzles, lessons, and game reviews for free. But if you want unlimited, you then subscribe. So we want to make sure that everyone, regardless of budget can access this amazing game, play this amazing game, and get these incredible learning tools. And most people do that and that’s wonderful. The small percent who want it unlimited will subscribe and that’s wonderful. I’ll also add that we have advertisements on the free tier and you remove the ads if you’re on the paid tier. But honestly, our advertisements on the free tier are very minimal. We could make a lot more money on advertisements if we wanted to, but we choose not to, because we’re not trying to make the free tier to drive people to subscribe. We want people to enjoy that free experience.

Robbie Baxter: How do you think about packaging the different tiers, free versus paid when what you have is so generous and rich for free and delivers on your promise, right? You can play, you can even improve, you can learn to get better, you can take lessons and puzzles and things to work on.

How do you as an organization decide what goes behind the paywall and what stays in front of the paywall? There’s this concept of a Rule of 40, which is how much you want your revenue to grow versus your profitability. Also the question of monthly active users, that number could be super high and both of those other numbers could stay flat, right? Should we focus more on revenue growth, user growth, member satisfaction, or margin?

Adam Mayer: Yeah. So we view revenue not as a goal to enrich shareholders, to enrich executives, to put us all on a beach someday. We view revenue as fuel for the mission. We want to make enough money so that we can reinvest it in the product, in our users, in our employees, to further the mission.

So when we have conversations about do we need to balance the free growth versus revenue, it’s really a question of how much revenue we need to build and put back into the business to grow this mission now. Yes, there are certainly business factors going into play and we have margins that we’d like to hit and revenue like to hit, but unlike any other company I’ve worked at, it’s not like, “We had to hit this number, do whatever you need to do to hit this number.” In other companies, it’s more about how we maximize revenue, profitability, and shareholder value. That’s not the conversation we have here.

We view revenue as fuel for the mission. We want to make enough money so that we can reinvest it in the product, in our users, in our employees, to further the mission. Share on X

Now, we are doing really well in revenue profitability and shareholder value, but it’s not what drives the conversations. It’s not what gets us to wake up in the morning, maybe me a little bit more because of my role. I’m not going to lie that part of my role is to have that focus. But overall in our executive meetings and the company, that’s not really how we think, which is quite refreshing, even though I’m sometimes on the other side of it.

But to answer your question about what goes in front of and behind the paywall and also like, how do you have a subscription business when you have such a compelling free product? And it’s a bit of a double-edged sword because, on one hand, I’m trying to put a business hat on, let’s take the mission aside for a second. I’m trying to drive as many subscribers as possible and I’ve got a very compelling free tier. So someone says, “Why should I upgrade when this free tier is great? Especially when I can get game reviews, when I can get lessons, when I can get puzzles on the free tier,” and guess what? A lot of people won’t upgrade because of our amazing free tier. And that’s just a reality.

But on the flip side, by giving them such easy access to the game of chess, easy access to taste our tools, right? You don’t get it unlimited. You get one a day, you get one a week, et cetera. The more people, the more they use the tools on the free tier, the more likely they are going to be an upgrade.

When I first got here, I was thinking, “Oh man, this free tier is so compelling. This is a real challenge for me.” It’s actually been somewhat the opposite. Our compelling free tier nurtures and grows the love of chess. And that’s what gets people to subscribe because clearly there is value to the paid tier.

Chess.com’s Free Tier Fuels Passion—The Value of Premium Keeps Players Coming Back.

If there was no value, there’d be nothing, but the more they use the free, the more they love it and the more they want to upgrade. The thing that I think is amazing about a free tier that some subscription services have and some don’t is we have a huge pool to market to, and it’s not paid marketing, right? We’ve got our own marketing. We’ve got tens of millions of people that are the low-hanging fruit who will potentially upgrade. So it’s actually a really good business model to have a compelling free tier because it just makes it that much easier to find your customers and upgrade them.

Robbie Baxter: Yeah. So I think about three reasons for having freemium, other than just being very generous and altruistic. There are many free subscriptions out there that have a founder who just cares a lot about that community and does it for free. There are a lot of nonprofits as well, where they’re just trying to break even. But assuming that you’re trying to run a business, freemium, number one, there is often a viral effect, meaning that when I play, maybe even organically, I’m bringing in other people. Like email which is the original example of virality. I send you an email and at the bottom it says, check out Hotmail, right? And then you sign up because that’s cool and it’s free.

Adam Mayer: Wow. Hotmail. That’s a long time ago.

Robbie Baxter: I know. That was the original. That was the original example of viral growth. The second great reason to have a freemium model is if there’s a network effect. That is for each paying person, each free or non-paying person that joins creates more value for the people who are paying, right? If nobody else were on LinkedIn it wouldn’t be valuable to the recruiters, the salespeople, and the job seekers who are willing to pay for their subscription.

And then the third reason is what you described which is that your driving behavior change. People don’t think they’re going to need the product as much as they actually do. And they keep bumping up against a paywall and eventually realize, “Wow, I actually really do use this a lot.”

Adam Mayer: And to your second point around the network effects, that’s huge at Chess.com, right? Because again, we have tens of millions of people on the site. I get value from everyone else who joined and the best example is at any time of the day, no matter where you are in the world, if I want to play a live game and we have so many variations of live games. You can do a fast game, a slow game, blitz, rapid, and different variants within five seconds. If not less, I will be paired with someone else and that ability.

By the way, our technology and the product team that enables that is unbelievable. We spend so much time and energy to make sure that you can do that is huge. And I think that’s a lot of the value of the Chess.com and that’s why community is a huge pillar of what we do as a company.

Robbie Baxter: The thing I was going to ask you is of those three elements, do you do all three, two, or one?

Adam Mayer: I talked about number three. Number two is huge. And number one is being viral. Certainly, when some person uses Chess.com, they’re marketing it. Our app is a viral marketing tool. If you’re on the subway and you see someone using Chess.com and because it’s free, they can easily be like, “Oh yeah, I want to download it. I want to play.” Bam! Done! And then we can play a game right away. This is not the subscription side of things, but on connecting, you set up friends on Chess.com and have a friend network, and you can play with your friends, you can play with strangers.

Then we have clubs, communities and you can have your own community. You can have your own chess club. So setting up all of that network and virality is huge whether it’s on the free tier or the pay tier. From a paid perspective, my acquisition costs are relatively low because I’ve already got this pool of existing customers on the free tier.

Robbie Baxter: It’s interesting. There’s a lot of analogies in what you’re saying. Another guest that we had on the show, David Lorsch, Chief Revenue Officer at Strava, which is also a very mission-driven organization. Trying to connect the world’s athletes. It’s a lofty goal.

Adam Mayer: You’d be shocked how many chess players are hardcore athletes, both professional and casual. There’s something about the passion. I’m always amazed by how in shape chess players are maybe even more than wrestlers, but don’t tell them I said that.

Robbie Baxter: That’s fascinating. So there’s a lot of overlap there. One of my next guests that I haven’t really talked about yet on the show, but he’s at Crunchyroll, which is another one of my favorite subscription kind of niche subscription businesses. And he was telling me about the overlap between anime fans, sports fans, and elite athletes. And it was the same thing. He’s like, “We do great with the NFL. We do great with the NBA.”

Adam Mayer: Crunchyroll was a partner of WWE when I was there, so there was a lot of overlap there as well, so I’m not surprised.

Robbie Baxter: I wonder if there’s something about people who get something out of fandom having these interests.

When we were preparing for this conversation, you said something to me that really struck me. You said, three tier companies want a single tier, and subscriptions with just one tier want to expand and personalize. As a revenue officer, I think you’re constantly going back and forth between How can we get the last penny? How can we optimize for each customer’s willingness to pay, ability to pay, desire for value, and recognition of value while keeping things simple, both for the subscriber, right? Because if I have to keep my wits about me, if I have to keep my wits about me to figure out what the right program is for me, how can I relax and trust you?

And then on your side with your team. As you’re trying to understand 35 million users, keeping track of it, and trying to understand trends, if every one of them is paying a different amount and getting a different feature set, how do you even know what’s working? So how do you balance that? How should a revenue officer think about their own monetization strategies? Where to start and then what to do as you try to expand revenue.

Adam Mayer: There’s lots of unpack there. I guess we’ll focus on the subscription specifically side of revenue as opposed to the broader.

To your first point, I’ll just say a lot of people and companies ask me, or we ask each other: What is the model for subscription packages or tiers that works? What’s the right answer?

Chess.com right now has three tiers and each tier has a monthly and a yearly option, so it’s six skews in total. And we’ll talk to a company with one tier and we’ll say, “Oh, how do you guys do that? Cause we think maybe we should be one tier, make it simple for everyone.” And they’ll say, “Wait. We wanted to ask you how you guys do three tiers because we need to diversify our offerings more.” So I’m always hesitant to say this is the right package or plan for a subscription product. I think it depends on your audience and on your business goals, etc.

But despite that, one of the most important things is that you want to make sure that whether it’s one tier or three tiers, it is very clear what the value proposition is of that subscription service and what the different value propositions are for your three different tiers. That’s one of the things when I started Chess.com that wasn’t so clear. We had a little bit of a mix of different numbers of lessons in one and then more lessons in the other. And you look at our tier structure and as a user, I’m not sure exactly why I want gold versus platinum versus diamond. So one of the first things we did was we made much clearer demarcations between what our three tiers are. I don’t want to overplay this because it’s not so cookie-cutter. We somewhat tried to make them different for different types of audiences. So people who wanted to have a bit more fun or a bit more into puzzles were in gold here and people who were into learning and really analyzing their games were in the higher tier. So we moved the game review to the higher tiers. It was much easier to say, “Okay, I can now look at your membership page, and more easily understand the differences between your different tiers and pick.” While I’m not going to tell anyone you need to have one, two, three tiers, monthly, or annual, make sure it’s very easy to understand the differences and make sure the value proposition is there, especially in a subscription business, because I might buy a shirt, thought it was great then obviously it wasn’t great and I’m out 30 bucks. I’m never going to buy that shirt again. But in a subscription, you need them to tab value and keep value.

One of the most important things is that you want to make sure that whether it's one tier or three tiers, it is very clear what the value proposition is of that subscription service and what the different value propositions are for your three different… Share on X

How do you acquire and retain subscribers? It all comes down to two things. What I’ve always seen in my career, whether it was cable, content, or a chess game. It’s about price and the product.

The other things that we spend time on and we should, whether it’s a customer care, or whether it’s getting the right special offer or the right marketing message, all of them are important, but at the end of the day, especially with subscription, they’re going to come and they’re going to leave if they’re feeling like the product is not valuable enough or it’s too expensive. That’s always my message to subscription businesses. Keep it simple. Make sure your value proposition is there and steady, and obviously make sure the price is right. Sometimes I’m surprised when I look at some subscription products that it’s not clear exactly what I’m getting and why I should stay.

Robbie Baxter: There’s the acquisition moment where it’s good enough to get them to try, but then there’s a retention moment, the moment that you have to keep a subscriber. It’s different from when you buy the shirt and if you spill spaghetti sauce on it the first time, that’s your problem, right? But if you wear it out and feel scratchy, or it doesn’t feel like the right thing to wear for work. It’s too bad it’s yours. But with subscription, if you subscribe, let’s say to Rent the Runway, if you don’t like the assortment they give you, you’re going to cancel. So that moment of transaction is just the starting line.

Adam Mayer: What I think is cool about Chess.com, like any subscription service, you have to keep the value. So you often have to introduce new features, or if you’re a content company like WWE, you have to keep introducing new content.

Keep it simple. Make sure your value proposition is there and steady, and obviously make sure the price is right. Share on X

At Chess.com, we are always innovating and we are always introducing new features to keep things fresh, whether it’s on the free side or the premium side. But the beautiful thing is the game of chess is over a thousand years old. And in itself just has this natural, and you can learn at the same game. I’ve been playing very intensely now for over three years, it’s the exact same game every day but with a different experience. I’m learning something new. So there’s a natural sense that it actually feeds itself well to a subscription model because even without the product changing, I feel like it’s a brand new product almost every single day.

Robbie Baxter: Amazing. Do you have time for a speed round?

Adam Mayer: Let’s do it.

Robbie Baxter: First subscription you ever had?

Adam Mayer: The Economist in college. That’s so embarrassing. My professor of macroeconomics told us all to get The Economist. So I did and I used to really read it hardcore.

Robbie Baxter: They have a really interesting subscription strategy, but a couple of things that they’ve innovated on. One of them is newsletters to make what was a periodical into a daily or even hourly. And the other thing that I love that they’ve done is let’s say you bought the Economist, and subscribed your whole team or company. You only have to pay for the people that are actually using it.

Adam Mayer: I remember in college, they’d have The Economist on their shelves, but they didn’t actually read it. It was a little bit of a trophy.

Robbie Baxter: Your favorite subscription today?

Adam Mayer: I am a New York Times addict. I subscribe to the physical paper on weekends, I subscribe to the digital content, all week. I use The New York Times games. We have a competition within Chess.com for Spelling Bee and Wordle. I am a huge The New York Times advocate reader fan.

Robbie Baxter: Awesome. A subscription that has inspired you with its freemium model.

Adam Mayer: I think Duolingo has a really good freemium model. My daughter and I uses it. It’s a great free service and she has not subscribed yet. I subscribed at one point, although I’m not currently a subscriber. Yeah, I think they do it really well where they give you, just like Chess.com, a product you can stay free for as long as you want and still get value, but enough taste of the premium that makes you want to upgrade if you’re willing and can afford it.

Robbie Baxter: Your wrestling name, if you had one.

Adam Mayer: The Flying Jew.

Robbie Baxter: Your favorite game other than chess?

Adam Mayer: I love the game which I haven’t played in a long time is Halo on Xbox. In business school, we used to play it. It wasn’t even online. You’d have to do a local area network, and we would literally bring four televisions to someone’s apartment or dorm, hook it all up via ethernet and we’d play. It got so popular that a professor started joining us as well. So I loved Halo. I’m trying to get my kids into it now. It’s not as hot as it used to be, but we’ll see.

Robbie Baxter: Advice to another CRO trying to balance a strong mission with a desire to be self-sustaining or even profitable as an organization.

Adam Mayer: A very strong mission, and if everyone’s focused on the mission, it will lead to strong revenue and strong profits. And a strong revenue and strong profit will help support and grow the mission. So they’re very symbiotic. Don’t be scared of trying to grow revenue in a mission-driven company, embrace it. They feed each other and it’s great. And it also makes you feel better in the morning when you wake up to know that you’re not just trying to make money for money’s sake, you’re actually helping a cause and hopefully helping lots of people enjoy life. And in my case, enjoy this amazing game.

Robbie Baxter: Yeah. I couldn’t agree with you more. And the great thing about working in so many subscription businesses is the business model itself forces you to take care of your customer for the long term, which makes money, but also gets you out of bed in the morning, feeling good about what you’re about to do.

Don't be scared of trying to grow revenue in a mission-driven company, embrace it. Share on X

Adam Mayer: Absolutely.

Robbie Baxter: Adam Mayer, thank you so much for being a guest on Subscription Stories. It’s been a pleasure.

Adam Mayer: Robbie, this is great. I learned a lot and it’s great to talk with you.

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That was SVP of Monetization at Chess.com, Adam Mayer. For more about Chess.com, go to Chess.com. And for more about Subscription Stories, as well as a transcript of my conversation with Adam, go to RobbieKellmanBaxter.com/podcast.

Also, I have a favor to ask. If you like what you heard, please take a minute to go over to Apple Podcasts or Apple iTunes and leave a review.

Mention Adam and this episode if you especially enjoyed it. Reviews are how listeners find our podcast, and we appreciate each one. Thanks for your support, and thanks for listening to Subscription Stories.

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About Adam Mayer

As SVP of Monetization at Chess.com, Adam is responsible for the company’s two primary revenue streams: subscriptions and advertising. Adam manages subscriber acquisition, retention, packages, and pricing. His team also runs Chess.com’s digital advertising business.

Adam has been working with subscription businesses for over 20 years. Prior to Chess.com, Adam was an SVP of Marketing at WWE, where he was responsible for customer acquisition, retention, and CRM for WWE’s subscription-based digital video streaming service, WWE Network. He also worked at Time Warner Cable, where he launched and ran the company’s smart home security business.

Adam received Bachelor of Arts degrees in both economics and international studies from Yale University and an MBA from Harvard Business School. He lives outside of New York City with his wonderful wife, always-entertaining two daughters, and loyal dog. He enjoys playing tennis, playing the piano, and – of course – playing chess!

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How to Build a Strong Subscription Business While Maintaining a Compelling Free Tier with Chess.com CRO Adam Mayer

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How to Build a Strong Subscription Business While Maintaining a Compelling Free Tier with Chess.com CRO Adam Mayer

Important Links

About Adam Mayer

A veritable blueprint for success in the new membership economy.

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