How Smart Product Managers Increase Revenue

Okay, Shay, uh, it's so good to have you on the podcast. We've been trying to get this scheduled for a long time.

I know, I'm so excited to be here. Thank you for having me.

Appreciate your patience. And, um, yeah, you look— you've had this really interesting career, largely in product, but yeah, across several different, really, really, really different industries, all very interesting industries. EdTech companies like EverFi, MetaFi, Yeah, Vertical Social Network, RallyPoint, and sort of like the military and veteran space, which is so fascinating. And now SamCart, which is really in the creator space. Yeah, e-commerce creators. It's a really cool journey. I imagine you've learned a lot about building product for a lot of different types of customers, lots of different empathy. And I think you've learned a lot about pricing and packaging as well. So what's the journey in your own words? How did all this happen? How did we get to now?

Yeah, the way you say it makes it sound like I'm a glutton for punishment, but I appreciate the kind words. Yeah, it's, it's definitely been an interesting journey for me. You know, I, when I was in college and undergrad, I did my undergrad at UC Irvine down in Orange County. I thought I wanted to be a doctor. Didn't work out. You know, I was taking the, the bio and chem classes and was doing okay. Nothing probably that was going to get me into a top-tier med school at the time. While I was sort of finishing my senior year there, I had my first introduction into startups. I got a marketing internship at a small music startup in Los Angeles, Orange County area. And so that sort of really opened my eyes into like my first real job sort of internship and was doing marketing and some project management and became some product ownership stuff and sort of that was sort of my segue. And then I ended up going to grad school and moving to LA to go to USC for a couple years. And that's when I really like got into business stuff and, you know, case studies and use cases and all the different things and was kind of lucky enough to get an internship there while at USC as well. And that sort of segued my, I guess, my journey and started a little bit of marketing, but then into product and been doing product. Yeah, mostly my whole career now, 8 or 9 years, which is crazy to think about because, you know, time flies, as you probably know. But yeah, I've really enjoyed it. And started my career at RallyPoint, which was a sort of a social network for the military. So kind of like a Facebook community for the military audience. And I don't think I've ever had a mission that I connected more with, you know, than our service members and veterans, just, you know, being a citizen in the United States. And so, you know, developing and building a community for them, ended up monetizing that and connecting them with, you know, military-friendly businesses like USAA and Navy Federal Credit Union and Ford in all these big companies to, you know, people who are looking for military members. And so that was really exciting sort of startup experience, first sort of product PM experience for me. I was there for almost 4 years and did a lot of different things. I wore a lot of different hats, as you probably can imagine, at the 15-person startup. So I really learned a lot and still am friends with some of those folks there from that experience. And Yeah, I segued then into education technology for a couple of companies. One was a big SaaS company and was bigger company, bigger teams, got bigger team experience and then moved back into sort of a smaller startup in edtech. And then now I've been at SamCart for the past, I guess it's been a little over 2 years now, which is an e-commerce platform for creators. So Yeah, kind of ran the gambit of industries there. You know, I love learning new things. I sort of have strategically positioned myself to be more of an industry generalist just because that's where my curiosity is. I love learning about new industries and new things, new customers. And so pretty proud of myself at sort of still a younger age, I would say, to get where I'm at now. You know, excited for the future and what has to come. But that's kind of my trajectory arc into product management for most of my career.

Yeah, it's a really cool story. You know, going back to grad school, you know, you got an MBA, you got an MBA at a good school. I'm curious if you, if you found pricing to be a central part of the curriculum.

Yeah, it definitely was. I even took specialization marketing classes in that program around pricing as well. So that was kind of my first foray into learning about how companies price things and different pricing models and usage-based versus tier-based versus, you know, consumption and all the different things I would say. And so there was definitely, you know, while during my second year or first year, maybe two, but definitely pricing was involved in different case studies as well, reading different ones and kind of learned a lot. Going into my tech career, I would say, was pretty beneficial for me. I really valued it.

So from there you jump into product and you jump into product first in sort of a social network, a verticalized social network. Then you go into product for two edtech companies, now for a B2B platform serving what I would call creators, which in some ways like sort of represent small businesses of one.

Is that a good way to think about it? Yeah, solopreneurs, SMBs, you know, we have some small brands as well. Yeah.

Yeah. And so kind of to what extent, you know, product across all three industries, but at which point was it, you know, kind of at RallyPoint? Was it in edtech? Was it where you are now with SamCart? At which point did product and pricing and packaging start to have material overlap for you in terms of your charter, your mandate, your purview?

I would say definitely really was the heaviest the last couple of years at SamCart. And the reason I say that, just because there I originally got hired at SamCart was not to work on SamCart proper, which I do now, but I actually got hired to bring a new business and product line basically zero to one at SamCart, which is still active and kicking today. So that had a lot to do with obviously not only building the product and building the features of it, which is traditional, more traditional product management, but also a lot about being sort of the product line owner of it. How we're going to price it, what's it going to look like, the messaging. And there was no go-to-market team really on that new product line. And so I was kind of the de facto head of it. And so, you know, me working with my boss, who was our COO at the time, was a really sort of valuable experience where product and pricing and packaging kind of came head to head in bringing that product line to market. And so that was a very sort of unique and special experience for me, was doing that my first year at SamCart.

Well, I'd love to spend time on that because—

Yes, let's do it.

This is a really meaty and interesting and valuable part of a SaaS company's journey is sort of the entry into multi-product.

Yeah.

You know, as you know well, as a software company starts to grow up, they start to add complexity. They start to add different go-to-market motions. They start to add different billing models. They start to add new product lines.

Yeah.

And when you're dealing with, you know, kind of complexity across those three vectors, how you support pricing and packaging, especially from a product and engineering lens, can get quite complex. So yeah, maybe you can just educate us on everything you've learned about going multi-product in a scaling software company. And maybe just start at the beginning, like when you were considering joining the company, how did you sort of consider the opportunity, the risks, like what made you really decide, I want to tackle this, this is, this is the right next move. And, and just give us a little bit of the lay of the land, like where was the business at the time?

Yeah, the business at the time, so this, I joined SamCart, I think it was at the very end of 2022, December, maybe January, uh, '23. And, um, when I was sort of interviewing at the time, there was a couple reasons that got me really excited. The year before, they had closed their big Series B for SamCart, the core product, which is our e-commerce checkout product.

And there's like an $80 million round, right?

Yeah, I think it was $82. Yeah, pretty much.

It's a big round. It's a big Series B.

Big Series B.

And this was— they raised that in 2021?

I think it was the very end of 2021 going into 2022, I believe.

Also raising at a really interesting time, right? Because the world's about to change like within a month.

Yes, pretty much, which was also very interesting. And so that had happened. And when I was interviewing in the fall of '22, I had learned, I had known that and learned that. And so I knew that they had raised that. I knew it was a very exciting time at SamCart. I knew they were growing. I knew what this position was going to be. And so that was the other sort of main thing that really excited me around the opportunity was bringing this sort of new idea conceptualized not only product but business line to market as another prong of SamCart under the SamCart umbrella. And so, you know, I had prior to that never really brought something pretty much zero to one. And so that was another sort of, you know, really enticing moment and opportunity for me to see if I can chew my teeth on and test myself with something that was a little bit, you know, well, a lot a bit more ambiguous and unknown of what the direction of it was going to be. And so I would say, yeah, the timing of, you know, interviewing with, you know, the Series B and how they were growing, as well as the combination of them expanding their umbrella, so to speak, and bringing this, you know, this product lead in that was going to bring this new thing to market, those kind of factors sort of sealed it for me in coming over here a couple years ago.

So had the product number 2, for lack of a better term, had that been developed or were they looking for somebody who could come in and figure out what was the next product to go after? What was the next problem to solve?

When I was coming on, they had ideas and I can get into what the product is, but there was basically a head of an engineering lead and a designer and they were looking to bring in this product lead. And so I think they had not really a roadmap, so to speak, but they had ideas and they were building out the framework of this new app and there was like I think it was live maybe for like a small number of customers, but very bare bones sort of prototype MVP style. And so I came in to really like drive the direction, the strategy of where we wanted to go. And, you know, obviously the roadmap and the feature set. So I would say, you know, aside from a few maybe early adopters from an MVP was pretty, you know, net new at that point.

Okay. So this is, so you come into the business, you've got this really interesting charter and mandate you're going to pursue. It's super nascent, right? Like there's a lot of ambiguity you've got to work through. There's a lot of definition that you've got to deliver to the business.

Yeah.

Tell us a little bit about like the product, the core product, and then tell us a little bit about like what was this new product and what did it— what impact did it need to drive for the business? Was this unbundling, you know, really popular feature into an add-on, or was this like a completely new product that was going to kind of create new entries into the business, or was it kind of pure cross, like pure upsell? Just really paint the picture for what happened here.

Yeah, so to give some context there, you know, SamCart is an e-commerce platform for creators, whether you're a solopreneur or you have a small team or an SMB, or maybe even a bigger small brand. But what we were noticing at the time for SamCart core product, our e-commerce product, was yes, there were some big sellers on our platform and our products who were ready to sell. But what I think leadership was finding and what I was finding coming into SamCart, you know, a couple years ago was there was also a lot of what we called newbie sellers. And so maybe they didn't have a product yet to sell. Maybe they didn't have an audience or a niche yet. Maybe they just had an idea but didn't know how to take the next steps. And so there was Obviously our big sellers upmarket who are making money consistently selling their products every month, consistently selling and making GMV on our, through our platform. But we had a lot of these sort of lower market, sort of entry-level newbie creators or newbie wannabe sellers who needed more help. And so as we saw a large chunk of customers coming into SamCart, I think they saw a lot of early sort of infant churn because these sellers were coming into this pretty sophisticated e-com tool who weren't necessarily ready to use it yet. And so I think the, the idea spawned for this new product line of, okay, how can we help this like pretty large user base and segment of these sort of newbie creators or newbie sellers starting out who need help getting over that initial hump to being ready for a more complex feature-rich e-com tool. And so that was sort of this new product line idea, helping those sort of newbies ascend up into more established scalable sellers, if that makes sense.

Yeah, it makes total sense. And I'll just play it back. I mean, because it reminds me of so many great businesses where like, you've got sort of like a core market, which is a more mature merchant, but you have a bunch of hobbyists who have all the potential in the world, but like they need a bunch of tooling and they need to eventually kind of become serious businesses and like the extent to which your products and your tooling and your content and your education can help them grow better for your business.

Yep. Yep. So that was sort of I was coming in to deal with and the product itself at the time started out as sort of a content platform. If you think about like a Netflix for creators or sellers. So when I came on and started this and started on this product line, we just had some videos from our marketing and production team on, you know, they were sort of video mini courses, as you would imagine on a Udemy or Udacity, where it was like how to make your first sale. And then it was videos and of course, content and how to, you know, grow your social media audience, how to get more followers. And so it started as sort of this, you know, online content video, Netflix style, to learn. But what really drove me was the potential to do a lot more. And so yes, we had the learning tools, but interviewing more creators than I care to speak about in the last couple of years, you kind of learn, especially these newbies, that you can't just watch something. You need to help them take actionable steps into doing. Right. And so that's kind of one of the big values that I learned in growing empathy for them. Like, anybody can watch a YouTube video or a piece of content, but it doesn't mean they're going to know what to do next or have the confidence to take that next actionable step. So what I did that first year was really drive the direction of other new innovative products and our features within that, within that product line to drive actionable steps. So an example of we built, we partnered with this company called Philo who does APIs for your social media. So we built this social dashboard product where you could basically come into our product, connects your Instagram, TikTok, YouTube, and then we would show you all these, all this cool data on your social media and your following. So how you're trending, where you're dropping, all the stats with it. And then on top of that, we would recommend our videos and our content based on your social media performance.

So is this the new product?

It was one of the sort of feature sets in the new product line. Yeah. So the product itself was called CreatorU. It's still alive and kicking today. And we, it would start it as those videos and those educational content course courses style for consumption. But then we built this social dashboard where a lot of our customers within CreatorU were watching the videos, but now they're connecting all their social media accounts so they can see their Instagram data and then whether, let's say their Instagram was trending down for whatever reason, we would recommend specific Instagram videos and courses to then watch and take to do better and grow.

Or you're taking them beyond just kind of shallow consumption and into action and into data.

Yep.

Did you, did you view this product as, well, did you view it at the time and then what did it become? But did you view it as like a sidecar product that would basically be like, top of funnel to create a lot of nurturing of basically not yet real merchants into real merchants? Or did you view this as like, this is going to be a revenue-driving product from day one?

So it's an interesting question. At the time, I thought it would be the former, where it would sort of be this sort of high-level lead gen kind of funnel system into SamCart, right? But what we were seeing at the time was it was just growing a lot faster than I had anticipated with creators who just didn't want even SamCart at all necessarily. Like we were just—

So you came in and you basically found product-market fit with ProductTube.

I hope so. I mean, that was the goal. Like we had a lot of customers who knew nothing about SamCart or maybe they knew but didn't buy. And so what ended up happening was I think within the first year of 2023, we grew close to 80,000 customers in CreatorU or 70 to 80,000.

Wow.

And so we built the social dashboard feature. I was then doing a lot of interviews with these creators that year and learning that a lot of them needed help creating their own content, finding their niche, finding their first product. And so we actually built an AI prompt tool into this CreatorU product where you could basically say, help me find my niche. And you would submit a, you know, sort of ChatGPT style, you would say, I'm this and this, and it would spit back responses for you. Or you would say, help me with, you know, 10 blog post ideas, and it would give you 10 blog post ideas as a response back, or help me with 10 Instagram post title ideas, and it would give you 10 title ideas based on the information you submitted it. So it became this sort of robust, tool that, or product essentially, that didn't just have videos. It added all these other features and tools in it, whether it was your social media dashboard in your data and us recommending courses based on that, whether it was this AI tool and helping you find your niche or giving you ideas. We also did specific customer journeys within CreatorU where you would go down the specific path of how to start from zero followers. And we would give you these exact roadmaps of what to do in some steps for videos, some steps for using our AI tool, some steps for connecting to the social dashboard. So by the end of the year, it became this pretty robust product that grew to a big group of customers that not necessarily were also using SamCart at the time.

Yeah. And so, okay. Originally hypothesis is this will be a top of funnel lead gen path into the core business.

Mm-hmm.

It becomes something different. It becomes a discrete product with quite a bit of use, at least tons of usage.

Yep.

Do you start pricing right away or do you wait and kind of layer on pricing after you see all this usage traction?

It's interesting you say that. One of the mandates when I joined was this needs to make money, right? So that was pretty clear, um, that this wasn't just a hobby that we were gonna And that's when I kind of shifted my mindset a little bit too, to like, okay, this isn't just about lead gen acquisition into SamCart for SamCart money. This needs to make money as a standalone product. And that was a very clear objective from my boss and leadership down that this product needs to make money. And so, yeah, we started, you know, thinking about pricing and packaging pretty early on in that Q1 quarter while we were building things of, Okay, what type of pricing? What type of packaging? What's the messaging? And so a lot of that was the onus became on me to kind of figure that out as we went. But yeah, it was pretty, pretty immediate that we needed to think about that because we need to make money from this.

Okay, cool. So at this point in the journey, you're building this new product, you've got a mandate to commercialize this new product, but You've not yet seen the really impressive usage spike. Is that, am I kind of understanding the chronology correctly?

Yeah. Yeah. It was later that summer, I would say, but yeah, that sounds right.

So how do you, I mean, you've, you've studied pricing in business school to some extent, like you've probably read some case studies about big businesses and historically how they've counterpositioned on price, but now you're like learning on the fly and you've got to persuade a bunch of different people in the business that you're correct. You've got to do a bunch of. Primary research with customers? Like, how do you go learn on the fly? How to tell us, like, what you did to learn how to do this?

Yeah, I would say two big— or yeah, two big, big things for me were one, understanding the market. So obviously we're not Netflix at this point or other sort of big video course style platforms, whether that's, you know, like Udemy, like I mentioned, or Netflix or whoever's in this sort of video attention game. Right. And so I think a lot of it for me was understanding the market, different sort of competitor options, researching competitors, analyzing sort of how they do their pricing and packaging for their products, whether that's different features, different benefits, different tiers. And so I think that was sort of one of the first big steps for me was researching, understanding some competitors, understanding some of the market. And then, yeah, another big one was understanding our audience within CreatorU, our customers. I knew they were creators. I knew they were newbies. I knew a lot of them probably didn't have big budgets. You know, you're starting out, you're not making a lot of money, or it's a side hustle, or you do it at nights and weekends because you're a mom or a dad and you have an idea. And so I think, too, really understanding, okay, we're not this big B2B enterprise where we're going to charge boatloads of money out of the gate for this tool. And so I think understanding that was pretty pivotal for me, like obviously doing the research and seeing what others and competitors or semi-competitors were doing, but deep, deep understanding of A, who my customers were and what their willingness was to pay and where they were at in their sort of creator selling journey. And B, like B and C of that, understanding like what's the value that our new product was going to deliver? What are our unique features? Not just the videos anymore. And so those sort of initial steps for me was really, I think, pivotal in the early part of that year while we were building.

Did you proxy price tolerance and willingness to pay largely through your competitive analysis or did you proxy willingness to pay largely through primary research where you got in front of customers and you really discussed perceived value and price sensitivity and preferred packaging schemas and things of that nature?

Definitely the latter. Definitely the latter.

So you went primary research and you did a lot of— I'm talking to a customer and I'm asking them point blank their willingness to pay.

Pretty much. Yeah. I had this whole interview. I remember it vividly. I had this whole interview Notion doc written out and obviously I had done some market research and some analysis there, but I really wanted to understand the customer. And since this is a brand new product, like where they were coming from, what their persona was, like I mentioned, learning that these are side hustle, mostly newbies, sellers who want to make some money online, or they want to pursue this idea on the side for now, or they want to make their first product. And so, yeah, going through the persona, going through what their needs were, like showing them this product live. Demos, Figmas, whatever. And basically at the end, like, what's missing from this product? And B, would you be paying, willing to pay X amount a month or year for it?

Okay. I wanted to ask you what you found to be sort of some of the most useful questions. You know, you could ask a question like, hey, um, what's the maximum you would be willing to pay for this product having seen it and let them define the price, or you could say, if this price, if this product were priced at X amount, you know, how likely would you be to purchase it? And then you give them several sort of multiple choice questions like, I'd buy it immediately, or no, I need to think about it. Sounds like you, you established a price point, but tell me if you played around with different questions to kind of ultimately find the approach that you liked the best.

Yeah, I definitely played around. Um, I had in my head sort of a price point, either whether that was monthly or yearly, but, you know, sort of half research, half gut feeling, half what I thought the product was worth, sort of that sort of system. But yeah, I really validated it through a lot of these, you know, face-to-face customer interviews and we did surveys as well. And so I remember, I think initially I would just be asking like pretty open-ended, like, what would you be willing to pay something like pay for something like this after kind of like either demoing it or describing it or showing some of the features. And, you know, as probably expected, pretty wide range of feedback, whether it was like, oh, I love it, I would buy it and pay a bunch of money, or yeah, I don't have the funds or the budget, you know, maybe I'm paying $10, $20, $25 a month for it. And so it's pretty, pretty wide scale. Obviously, you, you know, I did some analysis to maybe find a middle point, but it started pretty open-ended. And then by the time I had conducted enough of these and got sort of more research done and kind of what I was thinking the product was worth and talking to stakeholders and our leadership, I kind of had a range going, going into the latter part of this I had in mind. And then I would basically change the question, whether it was in survey format or even face-to-face, and give them the range of would you be willing to pay between X and Y for this product and getting basically a yes or no?

Super cool. And at the time, you couldn't— did you have— had you already kind of designed or at least kind of come up with principles for how you'd price? Like we're going to price for adoption or we're going to price for profitability? How are you thinking through kind of levers or questions like that?

Yeah, we were definitely— I wanted to price for adoption, just being a brand new product, wanted to see the adoption, wanted to see the usage, the logging, the time in the content, the usage of the AI feature, the connections of social platforms. So definitely was super interested in all that in at least the first part of the year or first half of the year when we were doing this exercise. And so I understood we were going to be priced lower than SamCart for what it was. I understood we weren't going to be, you know, this super high-priced tool out of the gate. And, but I think we landed on a pretty good range for what it ended up being. And I think it's a pretty similar price to this day as sort of what it's in the market now for. And so I definitely wanted to proxy against adoption and then as a lagging indicator, ended up making a bunch of ARR the first and second year.

And I think it's priced at $24 a month and there's like Basically one tier, although it looks like you have kind of a coaching tier that might kind of involve some professional services.

Yeah. Yeah. So from the packaging side of it, I always knew I wanted to go the subscription sort of traditional SaaS tier out. I wanted the recurring revenue. I wanted the MRR and ARR. That was pretty clear in my mind at the time. And yeah, we basically started off at one price and one tier, which was just for CreatorU.. And then as we built some of these more advanced features, whether it was the AI tool or, you know, the social dashboard and higher level support or direct coaching with one of our coaching specialists or whatever it was, I think they changed the name since, but it became, we had a pro or a max tier as well at a little bit higher price. And I think they changed it to Services Now, but we ended up before they moved me back to the e-com SamCart proper product or moved me over, we ended up having two tiers with some of those higher-end features at a higher price.

Yeah. All right. I've got some— what I'm really interested to kind of shift the conversation toward how this product integrates with the core product.

Yeah.

From a business perspective. But before we go there, you know, what is notable to me about this is like you executed willingness to pay with a ton of intentionality and a ton of thoughtfulness. And yeah, it worked. Um, but you also picked the right product, and I'm curious if, as you reflect on it, kind of what led to the right choice. Was it again a ton of primary research? Was it a ton of domain knowledge within kind of the core business, from founders to people that have been in the company for a long time who really understood the customer well and could guide you? What led to choosing the right second product? So successfully?

Yeah, it's a good question. I think one of the things that I leaned into a lot that helped me a lot was the domain expertise from some of the SamCart folks. And what I mean by that is both the co-founders are heavy, heavy creators themselves and started the company themselves. And one of them specifically knows this market and customer probably better than anybody I've ever spoken to. And so both of them are extremely knowledgeable SMEs around creators and these solopreneurs or solo entrepreneurs, whatever you want to call them. And so, you know, learning about SamCart, learning then, you know, all the domain expertise from them, so many like meetings with them and whiteboarding sessions and brainstorming sessions the first few months I was there, you know, even in person going to Austin, Texas, where our headquarters are, you know, pretty often was invaluable for me. They were so generous with their time, whiteboarding sessions, as I mentioned, just any question I had was more than available, which you can't say for a lot of co-founders, you know, at least my experience in the past. So I would say that was definitely invaluable to me. And then myself piggybacking off of that and just like my personality of a go-getter and just harnessing the power to talk to so many of these people, whether it was on a Zoom call, I took phone calls on the weekend with them, surveys, talking to customers, like such, such, I would say, blind motivation guerrilla style recruiting from my, from my side to really understand what the co-founders knew and who these people were. And I think those two things were, yeah, pretty, pretty pivotal for me.

Yeah.

Finding the right product.

The title of this episode is probably the power of primary research. That's sort of a new way here.

I like it.

Okay, so now take us into the business. Like, so now you get to, this is working, product number 2 is working. We need to start to think about how product number 2 complements product number 1.

Yeah.

Walk us through, you know, basically kind of the underlying analysis and kind of how that sort of informed what you all decided to do. Because what's sort of interesting and noticeable is that CreatorU is not sort of obvious on SamCart's pricing page. It's, yeah, it seems like it's a, you know, it's, it's sort of in the footer of the website. It is, it seems like it's a separate product.

Yeah.

Um, so kind of walk us through, because you could have, you could have approached this from a whole variety of angles, right? Like could have been an add-on, could have been, you know, a lot of things you could have done. Walk us through the decision-making, walk us through kind of how you landed on where you are today.

Yeah, I think, you know, a lot of the decision-making was early adoption success, early data success, I would say. We were seeing— I think this kind of goes back to my strategic pricing too, of pricing it pretty well and listening to customers and listening to our domain SMEs and experts about, you know, what content they wanted, where I wanted the product to go. Like I mentioned before, I think one of the biggest learnings for me was not just watching content or videos, but giving them the confidence and actionable next steps to move their product idea or their potential business forward into making sales or gaining followers or creating their niche. And so that came from all of those things. And I think we did a good job of decision-making in listening to the data, what we were seeing usage-wise, what we were seeing adoption-wise, all the primary research and feedback sessions I did of what they were struggling with, what their pain points were within CreatorU still, where they wanted to go, and talking to other stakeholders and team members and what was going on with SamCart. SamCart at the time was primarily investing in our main core product, which is our checkout experience. And so those are our checkout pages. Our sales pages, our different experiences that our sellers can choose from. And so we needed to get to the point of we need CreatorU customers to not necessarily use SamCart per se, but get to the point where they're ready for a checkout tool, no matter which one it is, and a payments tool, no matter which one it is. And so that drove a lot of the direction and strategy of where I went of, okay, we need to ascend them up from just watching videos. We need to have them do things in CreatorU. And that's where sort of the social products came in with the dashboard and growing their audience and helping them grow their audience. That's where the AI tool came in of helping them write things and create things and build things. That's where some of the other features came of like, now I have a product, now I have an ebook. We had some other technology that we use for helping them write content, whether that was a PDF or an ebook or something to sell. And so all of those things outside of just videos and courses, I think really brought them to actionable steps and insights to bridge that gap of, oh, I have an idea to wow, now I have a tangible product or a digital product. Now I'm potentially ready as I build this product and as I grew my audience and with the help of CreatorU to then go out and use Great if it's SamCart or a Shopify or a Spiffy or whatever else it is to try and sell this. So that was kind of a lot of the three-prong approach, I would say, if that makes sense.

Yeah, cool. Tell me if I'm interpreting this correctly or incorrectly. Like, as I was preparing for this conversation, sort of what was evident to me was SamCart is for a more mature creator merchant, if you will. CreatorU is for a less mature creator, somebody who wants to be a creator and is sort of in the beginning of their journey. Therefore, from a positioning perspective, they're really kind of discrete products. And though there might be funnel from CreatorU into SamCart, they do act quite discreetly. And it's really difficult to know potentially when there starts to be overlap. And so from a positioning perspective, the business has said to itself, let's position SamCart for the more mature merchant. CreatorU will be a resource that we link to, but it won't feature heavily as kind of a component of our core offering.

Yeah.

And we expect a lot of volume to find CreatorU sort of independent of kind of knowledge or awareness of SamCart. Am I interpreting the situation correctly?

Yeah, yeah, I think you are. I think, you know, we ran our own customer acquisition to CreatorU. We ran our own ads. We had our own, obviously you've probably seen the website and different landing pages and stuff like that that highlighted CreatorU solely and independently. And so I felt at the time definitely pretty strongly that this was a unique standalone opportunity, unique standalone product that we had a whole team against. So it wasn't just a lead gen page into SamCart. We had me and engineers and a product designer and a product marketer that worked under me for a while during the second half of the year as we saw growth. And so yeah, definitely I think I achieved the goal of making money where by the end of year 1 or year and a half, we were doing $9 to $10 million in ARR just within CreatorU.

That's incredible. Okay, let's shift into 2 topics. One is I want to understand organizationally how the business started to build a practice, a discipline, a muscle around pricing and packaging, especially in what had become the context of two products.

Yeah.

Was— were you spearheading pricing and packaging? Was there a pricing committee? How often did you guys meet and talk about pricing? To what extent was there like a lot of behind-the-scenes analysis coming out of either product or FP&A? It's just like, how did you guys really operationalize a muscle around pricing and packaging to the extent that you did?

Yeah, yeah, we definitely did. You know, I was always of the mind that pricing in particular is one of the most strategic levers that a business has. And I still sort of believe, or I still believe that, and it's critical to approach it not only thoughtfully, but in my mind, collaboratively, you know, doing CreatorU and being the de facto, I guess, product line leader for it and bringing it to what it is now to market. I never wanted to operate in a silo for pricing. I always wanted it to be a cross-functional effort across our departments because I have my knowledge about the product, but my boss, you know, who was a COO at the time, had probably more finance knowledge about SamCart or CreatorU as well and marketing. And so I definitely wanted to lead with committee and we, we put together basically a GTM or go-to-market team. And so we had myself representing product and I felt my job was to really understand the product, obviously the solution, what we were delivering to customers, the feature sets, you know, leveraging, you know, any customer research or data that we had and competitive analysis. You know, we had our, we hired a product marketer who really focused on the messaging and the copy and the content of what it was going to say going into our creator persona at the time. And then, yeah, my boss and one of the co-founders who kind of represented from an executive leadership strategic kind of whole encompassing level.

So yeah, were you also the voice of engineering in that committee or was engineering represented?

No, I was, I was pretty much the de facto product engineering person, but Yeah, the way we operationalized it, we formed this committee where we had sort of those four heads of the snake, so to speak, in those four departments. And we met, I think weekly going into it, but then biweekly as we sort of got in cadence and I did all this sort of, I love Notion. I love the product. And so I did all these sort of tables and tiers ideas and Notions and what I thought was a base tier, what I thought which feature would go in, you know, in which tier, obviously I had my pricing range that I was doing primary research on and, you know, formulating in my mind. And so, yeah, we had a lot of healthy debates and meetings around what would be the final price, what would be the monthly versus annual, what would be, you know, the full feature set was in the original tier, but then we went to our pro or max tier and then what was going to be in that, what was the differentiator in that. And so, yeah, we operationalized it in my mind pretty well of having the 4 heads to this sphere and being able to each bring our knowledge in different areas of the company into making the best pricing and packaging for creator customers, I think.

Yeah. So a few takeaways is one, you made this cross-functionally representative and you established sort of a habit around revisiting it regularly.

Yeah, very regularly.

And it was supported, I imagine, by like obviously the cross-functional perspective in the room, but also you were well armed with all the data that you were seeing out of both products.

Yeah. Yeah.

A big part of operationalizing this is, you know, what works within the actual application and the business systems. Um, from how you gate features. I mean, if you look at SamCart's pricing, it looks like it's, it's tiered pricing, largely differentiated by features that would be more appropriate for businesses as they mature across the spectrum.

Right. Right.

And so you've got feature-based tiers. You've also got this separate product. Talk about how this works from, from the context of like in the systems, in the product, feature gating in the product, handling entitlements, handling subscriptions. Paint a picture of how you guys have designed your own pricing implementation.

Yeah. So I would say, you know, the way we've sort of designed it and I guess systems and tools-wise is kind of, I would say a combination, you know, we have our sort of the pricing engine itself where we sort of define and manage the structure at the time, which was the tiers and then the pricing of it. And then I think we even went in for like the new AI tool or feature at the time. Some like we were teasing it, I think in the basic tier based on usage base. So you could do—

When you say, sorry to cut you off, but when you say pricing engine, was this like your billing system?

Yeah. So like our, you know, our CRM and billing systems, I think our CRM at the time we were using HubSpot and then Stripe for billing.

Okay. So Stripe for billing, HubSpot for CRM. And then from an application perspective, like what's governing access to the app? Is this like some feature flagging system? Are you using like JWT tokens? Are you managing access through the database? Like, do you know how that's working?

I'm pretty sure from a, yeah, from a governance, we use feature flags in our admin system.

Are they homegrown flags or are you using like a vendor?

I think they're homegrown. I'm pretty sure.

Okay.

So the way—

So you're gating access to the product based on tiers.

Yep.

So your engineering team has like built a lot of logic between your application and the billing system?

Exactly. Yeah.

You've built in some ways like a homegrown entitlement system to handle this?

Yes, pretty much. Pretty much. That's correct. So yeah, we would have our admin tool and we would build flags and then to give certain flags to certain, you know, sets or tiers is how we did it. And we did all that on our own backend, essentially.

And how automated was that? Because this is a business, this is a volume business.

Yeah.

So you've got thousands of customers. So is this entitlement system sort of really robust and flexible in automating kind of access based on, you know, assignment to plan tiers or is it? Individual customer by individual customer?

No, it's automated. Yeah.

Okay. Yeah. Cool. So you want to make a pricing change, and let's kind of paint a picture. Like, how does somebody upsell into SamCart from CreatorU? How does that end up happening within the systems?

So within CreatorU, there was within your account, I believe, and this could be different now, but I believe we put SamCart in there. So if you wanted to purchase SamCart as a combination of CreatorU, you could. And so if I was on the basic CreatorU plan in my billing account settings, I could see my current subscription of CreatorU. There was an option when we launched Pro or Max tier to upgrade to that. And then we also had the option to upgrade into SamCart. And so you would then purchase SamCart, go to them. Purchase, grow, launch, or scale, whatever tier you want. And then that would be managed in your central location of the SamCart application, if that makes sense.

Yeah. Cool. All right. We're running close to time and I'm curious.

Already?

You've described, you've harnessed your inner MBA student and you've described a case study.

I try.

And the case study was you come into a business and you launch product number 2 and you get it to $10 million in year 1.

Yeah.

And a lot of that comes from, you know, this isn't cross-selling into the existing customer base. This is like a new product for new customers.

Correct.

What do you, when product managers that are younger in their career come to you and they're interested in pricing and monetization?

Yeah.

What would you advise them to kind of think about or go do to really kind of learn on the fly as you did and master pricing and packaging as a discipline that can be really accretive to someone who's leading product and somebody who who loves product?

Yeah, it's a great question. You know, I, I would say don't be afraid of it. I've spoken to a lot of, you know, even myself when I was younger, younger PMs now who don't necessarily want to get involved or think it's their responsibility or that's on marketing or the exec team to figure out what we price it as. And I think that's the completely wrong mindset to go about. I think you as the product manager want to communicate the value of the product and understand your customers and what they're willing to basically pay for it and be willing to ask what they're basically willing to pay for it. And so I think the biggest thing you can do as a younger PM is think about pricing early. Like don't be afraid of it. Don't shy away from it. Don't think it's somebody else's responsibility to figure out a price for something. You figure it out and you do that by some of the examples I mentioned, whether that's doing market research and looking at some of your competitors and how they price and package and do they do tiers? Do they do scalar model? Do they do something else? Do they do usage-based? Like, you know, whatever it is, find out what other companies and products in your market and what your competitors are doing and then do the primary research too. Like get in front of your customers and figure out Hey, this is what we're building. Show them the demo, show them the prototype. If it's a new product, great. If it is existing product, fine too. And see, like, would you be willing to pay more for this? Would you be willing to pay X amount for this? Would you be willing to pay for this at all? Right. And so I think those are two of really critical examples of getting in there early. And I think a third one is understanding, you know, the segment that and of the packaging itself. So is your business a SaaS business? Are you going to offer multiple packages like a basic, a pro, and enterprise? Are you going to segment based on deeper features, more advanced features in higher tiers while offering, you know, essentially lower tiers or a freemium model or, you know, any sort of pricing model you can wrap your head around in segmentation, I think is really important too. And just iterate on it. Like talk to your coworkers, talk to your committees, talk to your, your stakeholders who are maybe more experienced than you and maybe have done pricing before and learn from them. But I think those three things of look at the market and your competitors, do your primary research, get in front of your customers, ask them these pricing questions and learn about, you know, your segmentation and how you're going to package this all together are three of the most important things you can do and do them earlier rather than later.

I think they're terrific lessons. And I think that there's, to me, there's a subtext to what you're saying, which is if you want to go be in product, you should want to build products that make money.

Yeah, exactly.

And you should hold yourself accountable to delivering enterprise value by shipping products that drive the commercial interests of the business.

Yes.

And you can't do that unless you really deeply care about pricing and packaging.

100% agree with that. 100% agree with what you just said. Like, you build things obviously to solve a problem and solve a human problem. At the end of the day, you want to make money and the goal should be revenue and make this, you know, make some money. And so to do that, you need to understand all these things and you need to get into pricing. And I think product is the host for that even. And like you have your committees and your cross-functional teams and your go-to-market teams to support you. But at the end of the day, it's, it's the product that's going to bring the value and it needs to be priced appropriately based on that value. And that product managers are 100% need to be involved.

Well, and then, and then you can extend that even further, right? Because like pricing becomes an extension of product.

Yep.

You've described people buying CreatorU and then buying SamCart, like that doesn't happen unless you've seriously and thoughtfully considered the experience of the customer with billing experience or with pricing experience.

Yeah.

Shay, what's the most important moment of your career? Like the singular specific moment that you view as an inflection, it changed the whole course.

Yeah, man, that's a great question. So many good experiences, so many good moments. I would say a pretty pivotal experience and inflection point for me was was going from RallyPoint to EverFi. And there's a couple of reasons I say that. One is because RallyPoint was a great experience. It was such a small startup though, and it was basically this bootstrapped, tiny little house of operations. And when I went to EverFi, it was really my big experience in a big B2B enterprise edtech company. Like a, you know, not a FAANG company, but a big sort of privately held still company where it was a lot bigger organization, a lot more people, a lot bigger teams, getting experience across bigger teams, more resources, more scope, more alignment. And so that was sort of a big step for me and a big moment of my career to like, you know, hone my product management chops, so to speak, across a much larger organization, whether that was getting better at communication, better at stakeholder management, saying no and why to things and all this sorts of things. And so I think going into that environment really helped me. And the other reason I say EverFi is because I had a really great boss at the time. She was the VP of product and I learned so much from her. And I think a good manager and boss makes all the difference in the world because I've had some bad ones in the past too. And so there's, you can tell when there's a difference. And so she really, you know, was a servant leader for me and not only learned about product management, but just learned about collaboration and camaraderie and support and just like what a real sort of mentor-mentee relationship is. And so that was an inevitable experience for me. So I think EverFi, moving to EverFi, for those two reasons and I, and it led to an acquisition, you know, it was a sort of a light at the end of the tunnel.

Such a cool story. Yeah. Shay, this has been so much fun. So instructive. Thank you. Thank you for doing it. People can find you on LinkedIn and they can, um, learn more about what you're doing at SamCart and—

Yeah.

FreeRU.

Absolutely. Yeah. I'm on LinkedIn. I'll give you my personal email. You have it probably, but yeah, reach out and I thank you for your time. It was, it was great. Thank you for having me.