Monetizing SaaS: Episode 9 with Lindsay Trinkle, Co-Founder of Makeswift

All right, Lindsay, it's so fun to be here with you. You're an entrepreneur, you're an operator, you've run ops for companies like Landy Lion, you've done program management for venture funds like Atlanta Ventures, you've co-founded and run ops for Makeswift, which was recently acquired by BigCommerce. Congrats. Can you, can you tell us about your career journey and what were the steps along the way? How'd you get to now?

Yeah, um, well, thanks so much for having me, Fynn. I'm so excited to, to be chatting with you about this, and excited about what you guys are building at Schematic. So it's great to be here. My career journey has been an interesting one. I started out in sales and marketing and got the opportunity about 4 years into my career, just figuring out, you know, where I wanted to land on the digital marketing side of things. I got the opportunity to work with David Cummings and the folks that were building Atlanta Tech Village. It was right after David exited Pardot and had the vision for Atlanta Tech Village. I was one of the first employees there. So I got to be on the ground level of building what is now a huge part of the tech community and the tech and startup scene in the Southeast. And that's really where I got bit by the entrepreneurship bug. I mean, it's very easy for that to happen in that environment. I was doing a lot of things around creating programming for Tech Village members and then working with David on the early iterations of his venture fund. I got to interview a lot of startups who were looking for investment. We had a scholarship program for students, so I got to talk to students as well who were looking for investment to get their ideas off the ground. And it was just really fun. And I started realizing as I was, you know, working with them and helping them some on the marketing front, that there was just so much, so much energy around building companies and, you know, coming up with new ideas and taking those to market. And I just wanted to be a part of that as much as I could. So I eventually left there. I did some time freelancing, doing, you know, marketing on my own. I did work at an agency for a little while, and then I ended up meeting Alan, my co-founder at MakeSwift. At the time, Landing Lion was his, his focus. And funnily enough, I ended up being Landing Lion's first paying customer. So I had my own marketing agency. And I was, I was definitely like, this is the era of Unbounce was new. Like there was a lot of no-code tools that were really new and exciting and I loved that kind of thing. So I was always trying every opportunity that I could get my hands on to work with no-code tools. And then Evelyn was introduced to me by a mutual friend here in Atlanta. And I had actually just paid for an entire annual subscription to Leadpages. To use for my clients. And I was, you know, okay, it was fine. It was like, it was gonna fit the bill. But then when I talked to Alan, he was like, just give Landingline a try and let me know what you think. So I did. And the UX that he had built was like, it was everything I'd been looking for as somebody who is not necessarily a designer, but I know what I wanna build. I know what, you know, my clients need. So I was, I was always just looking for something that would let me take what was in my head and bring it to life. And that was the first time I was ever really truly able to do it was Landing Lion. So I paid him an annual subscription even though I just paid LeadPages and didn't know it at the time, but I was his first paying customer. And a couple years later we reconnected over coffee. I'd been using Landing Lion nonstop and annoying the whole team, you know, just with feature requests and bug fixes constantly. Just love the product. And he ended up inviting me to join. And that wasn't really at the time, I wasn't planning to join another startup. I was kind of thinking, okay, I'm going to move, you know, maybe more to a more corporate sort of role. But I just, I couldn't say no. He's very compelling. He's a good sales guy, but he also just the vision. I mean, I had been bought in since day one, so I joined the team and that's kind of what led to where we are now.

Such a, such a great story. So to, to MakeSpace vision, talk to me a little bit about the vision of the business and the insight that, that kind of has, has catalyzed the business over the last few years.

Yeah. Well, like I said, we were a landing page builder to start. And when I joined, we were kind of hitting this inflection point where a lot of the users of Landing Lion were doing what I had been doing, which was trying to build full websites in a landing page tool. And so we were seeing that happen, we were trying to figure out how do we best support that. Miguel, our CTO now, had just joined the team and he was really, had some very cool ideas about how we could leverage React and, you know, React components to make the visual building experience even more extensible and more applicable to a broader range of use cases. And so as a team, we started exploring what it would look like to rewrite Landing Lion from the ground up and create an actual website builder using some of those principles Miguel had in mind. And so we started exploring that. This was 2018. Miguel and I joined within a month of each other and we decided at that point we were going to do this rewrite, build MakeSwift and focus in on that. And so I guess it was 2019 is when— yeah, February of 2019 is when we decided to officially go all in on that. And we ended up taking the team down to just the four, well, who are now four co-founders, Andrew, Alan, Miguel, and myself, and going all in on the Makeswith side of things. So we did a lot of interesting, we made a lot of interesting decisions. We decided we wanted to make sure that we kept the Landing Lion customers happy because we had a really great customer base. And so we ended up selling the IP for Landing Lion, which was really, exciting. We had a really great opportunity there, but we kept the brand and the customers and we migrated them over to what we were building with MakeSwift. And so we, at the time, were focused on just trying to get parity with our landing page builder, but we had this bigger vision for a much broader scope of what you could do with the product. So we were kind of trying to do two things at once on that front. The vision that we've had since day one really has been to become the ubiquitous UX for building sites. On the internet and kind of the next iteration of that. Like, I, I think of WordPress as the ubiquitous experience for building websites since the beginning of the internet, essentially, right? I think that we're moving into a new phase of website building, and what we're trying to do is become that, you know, standard, the de facto standard for how you build websites in the future. And so we were, we were working on that vision with MakeSwift serving the customers we have from Landing Lion, moving in this direction, capitalizing on a lot of the changes in web technologies that have happened over the last, you know, 5 years or so. And we really kind of hit, I think, what I feel like was our biggest like milestone in July of 2022 when we released our component API. So that was the first time that you could not just build, you know, a no-code site in Mixwith, but you could actually kind of pop the hood open and extend your site with custom components. And it was a really unique experience. It still is a very unique experience right now. There's not a lot of tools that do this, but allow you to do a lot of visual building from the gate. You can get almost all the way there, you know, visually. And then you, when you need something custom, if you need a bespoke component, bespoke functionality, you can just drop in that React component into the visual builder and still have that whole canvas and that visual context that the marketer needs. So Once we were able to release that in July of 2020, I feel like the vision for Mix really started to come together. Or 2022, July of 2022 is when we released that. And then we actually started talking to BigCommerce a couple months later. So fast forward, now we're here.

Well, and so it sounds like BigCommerce would share that vision. There's a next phase of how we build, how we build sites.

Yeah, yeah. And that's what's actually been so cool. Joining the BigCommerce team and really the reason that we took this opportunity was that there was so much alignment and how we saw the future of how the market is moving when it comes to website building. And they obviously are coming at it from an e-commerce space, but they have just a really, really exciting vision that was very much in line with the way we think about marketers and developers working together on websites. So what's great about the opportunity with BigCommerce for us is that We're maintaining our independence as a brand. So we continue to, you know, we're selling to not just BigCommerce customers, but to, you know, any marketing team that wants to visually enable their website. But with BigCommerce, we have a whole ecosystem already waiting for us, which is really great. We have partners and customers that are really hungry for this type of solution. And we're able to start really refining the e-commerce use case for our tool, which is exciting because it's a perfect place for us to play. It's hard to think of a website that people need more agility around than an e-commerce site. You know, you need marketers to be able to make changes quickly, but your performance has to be top notch. You can't sacrifice on the quality of the infrastructure and the tech. So you really have to have best of both worlds. And I think that we kind of are the piece that, that brings that together for those customers. So it's really— I love it.

I love it. It is so compelling when you zoom out and when you think about building Make with, but just building SaaS products, digital products in general. Are there big market forces or inflections that you yourself are particularly interested in, compelled by, thinking about a lot?

Yeah, um, yeah, I love this question. Um, I think that this is, this is something I think about a lot. Um, I think that especially with, especially now with AI and just the way that technology is becoming more and more accessible to every type of person and function. I think marketers and other non-technical folks are gonna become more and more technical just naturally. You know, I think for a long time marketers have been like, do I need to learn to code? And how technical do I need to be? I think just naturally with the tools that are coming, you know, into our, our realm right now, we're able to become more technical more quickly. My background's in marketing, so I speak, you know, about myself in this context a lot. But I think that as marketers become more technical and as developers understand, you know, the ability for marketers to kind of play in that space, I see this merging of the two. It's not, it's not even emerging. I think that we talk a lot about, do we need to eliminate a developer from the marketer's workflow or do we need to just make it only developers working on a site? What I see is that marketers can become more technical. Developers are going to be able to work within systems that enable marketers more, and that relationship will continue to evolve and change to where, um, there's not as much of the silo that we've had in the past and kind of the tension between the two roles. And so in general, that's pretty broad, but when it comes to building websites, I see our tool obviously as a part of that move and that shift, um, and just kind of bridging the gap between the two and redefining how those two functions work together. So that's something that is exciting to me.

I love it. Yeah, resonates strongly. So, and I think it's a good segue too into something I'm really interested to get your take on, which is monetization and B2B SaaS. And this is a broad subject. It's a complex subject. I think monetization is getting more complex for companies to figure out how to support. A lot of this comes back to, you know, you're trying to support multiple sales motions, product-led, direct sales. You're trying to support different billing models, the rise of usage-based. A lot of this comes to trying to figure out how to support a multi-product journey. Maybe you've been acquired and now you've got to figure out how to sell multiple products. Can you share a little bit about your experience with monetization and kind of what makes it challenging, what makes it complex? What have you learned?

Oh yeah, so many lessons learned, Fred, over the years. I think that the biggest thing, as I was thinking about some of these questions ahead of this conversation, the biggest thing that I think that I've learned is how critical it is to bring monetization into your product strategy early. And just thinking about how are you going to price this product as a part of the full vision, you know, because it's very easy to like build product in a silo and not really think about go-to-market, not really think about pricing, not think about any of those other functions, but those two have to go together. So I think the one— a challenge that like our team is very, very product-led. We're very, technical, we're very passionate about the product experience, you know, really, that's our sweet spot. So figuring out how to, in every, you know, product decision that we're making, also consider how are we monetizing this? How is this going to, you know, enable growth in our products? You know, how are we trying to sell this? Is this feature really going to be primarily sold in an enterprise selling motion, or is this going to be something that we're leveraging in a PLG motion? Having those conversations more holistically upfront has been something that we didn't do it great in the beginning. And I think that we're getting better and better at that over time. And I just think it's one of those critical things founders need to think about.

To that idea of getting better constantly, the pursuit of improvement, what techniques have you found to be kind of useful in that pursuit? How can companies get better consistently around pricing, packaging, monetization as a practice?

Yeah, I think, I mean, this is like kind of just like a de facto answer, I feel like for a lot of questions, but talking to customers, I mean, for me, that's a huge one. I, I have had to get over the, like kind of nervousness you have as a founder to be like, okay, here's a price point. Like, how do you respond to this? Or would you be willing to pay this? Or, you know, what do you think that our product is worth? What's the value that this would give to you? And for me, that has been such a huge, a huge, help in figuring that out because a lot of times like our assumptions are wrong. You know, sometimes those conversations will validate your assumptions, but a lot of times your assumptions are wrong. And, and I think that we, I've experienced, I think a lot of founders experience this, that there's like a higher willingness to pay if you're asking the right people. And so you're often underpricing your products. But then there's also times where, you know, you, you are valuing something and you're not communicating it effectively enough. And so, you know, the customer isn't seeing that value. And so you can kind of really to tease out a lot of those discrepancies. I think A/B testing your pricing and doing a lot of pricing experiments like that are so critical too, but I think you have to have both pieces. And I think in some ways we've almost like swung so far to testing everything and getting quantitative data around everything that we get comfortable in that. And I think there's this level of comfort that we need to continue to build up around having those conversations with customers as well.

Yeah, 100% agree. Imagine we're talking in front of a room of, um, 20 other ops leaders, products leaders that are at early-stage companies. If you had to package everything you've learned about monetization into here are the 3, 4, 5 mistakes to try to avoid, what would you say?

Um, I would say, okay, so I think that Thinking about, you know, your products and your pricing holistically from, you know, the get-go, like I was saying, is critical. I think also underestimating the importance of what pricing does for your brand is something that I think is really, is something that a lot of founders have been thinking about. Like when I, again, I come from a marketing background. When I think of branding, I think of like, okay, what's the experience that the customer is having of my brand. That's ultimately, no matter what I'm putting out there around my brand, their experience of my brand is going to be what ultimately is my brand to them. And so pricing is such a tangible piece of that. It's something that tells your customers, hey, this product is either for you or it's not for you. You know, a lot of times if you go to a pricing page, you'll be able to tell, okay, is this gonna be a fit for me or not? Just from looking at their pricing table. So I think, I think we, we don't, we kind of undervalue the importance of pricing as kind of a part of your branding as a company. And we're not taking that seriously enough a lot of the times. I think founders are just like, let's get it out there and test and test and test, which is fine, but you have to also really, really think about the, the value and the importance of your pricing strategy to your overall brand decision positioning. So yeah, thinking about it holistically from the product development, thinking about it as part of your brand, And then I would just say not talking to enough people, not getting enough diverse opinions. I think that again, it's also easy to talk to the customers that you know are going to give you the answers you want, you know, making sure that you're talking to a diverse enough set of customers or prospects who will give you real feedback. I think those would be, those are the 3 that come to mind for me.

Those are great. I know you guys have iterated on pricing and packaging throughout Makeswift's history as companies must do and always do do, but How are you pricing and packaging today? What does it look like?

Well, we actually are just about to release an updated pricing model. We've been, as we are going to market with BigCommerce, there's just a lot of new data that we're trying to analyze. It's a new customer base for us. We really weren't focused on e-commerce prior to this. And so we've been able to leverage Price Intelligently to do a pricing study for us, which has been really great. It's given us a lot of data that we never had before around willingness to pay, just different features, their value to the customers, just a ton of information. So we actually just got that report back, so I'm still digging in and processing it. But we're about to shift our pricing model to where we have some self-service plans, and we're really focusing in on, on that early onboarding self-service funnel where folks can come in, start for free, and experience the value of the product, layering feature teeth in so that they move up in the pricing model at the right frequency and then figuring out how to incorporate our pricing strategy with BigCommerce's sales team. So that's another big thing for us right now. We've gone from just me, founder selling, to we have a whole sales team now that we're enabling. So we're, we're thinking about it from a much like broader perspective than we have in the past where we've got this PLG motion, but we also have, you know, full enterprise sales team and we're trying to make sure that we have enough pricing enough pricing levers to make sure that we're creating that journey in the best way possible. So yeah, it's fun.

We've—

this has been top of mind because we're thinking through a lot of different elements of it right now.

Very good. This has been so much fun. Thank you for doing it. A couple of closing questions. What's been the most influential or formative experience for you professionally?

I was thinking about this question this morning and This is like, this is really more of just a moment in time that kind of shifted a lot for me. So I hope it counts as an answer to this question. But when we decided to pivot towards Makeswift and I became a co-founder and we officially made that decision, it was a hard decision in a lot of ways because we had some team members that we had to let go and we had to refocus the company. But I also actually, my husband and I adopted my daughter within a couple of weeks of that happening. And the timing wasn't, we weren't planning on want timing to line up that way. But it was one of those moments in my life where I was like, okay, this is all kind of happening at once. And am I going to dive in and go for it and bet on myself and bet on this team that I really believe in and this vision I really believe in and bet on my family that we're going to make this all work? And I did. And I'm really, really glad I did. I have zero regrets. Obviously, it's worked out really well for me. But I think for me, that's one of those moments that I hold onto because It's very easy as a founder in whatever situation you're in to be overwhelmed by all the circumstances that happen at once. I mean, founders who've started companies during pandemics or, you know, in really tough markets, like whatever it is, there's always just so many ancillary challenges that you aren't expecting coming in at once. And I think that when you have those moments where you do bet on yourself and you're, you're excited and you know you're in the right place and you're going to go for it, even though it feels crazy, like I think that's, that's where the magic happens. So I think for me, having that moment is just going to continue to propel me to look for those moments in my career as I move forward.

Thinking in bets. I love it. Yeah. Where can people find, learn more about Makeshift and connect with you and learn more about you?

Well, makeshift.com. I have, I have a personal website up at LindsayTrinkle.com, but I have, I'm actually working on redoing that with some new Makeshift components. So you can take a look at that. It'll be kind of coming soon. And then yeah, on Twitter or X, @makeswifthq is our handle and we're on there. Love to connect.

Thank you so much for doing this, Lindsay. Great to be with you.

Yeah, thanks, Fynn.