Episode 837 | How Do You Learn Product? and Optimizing Your Trial Funnel (with Ruben Gamez)

Rob Walling (00:00): Welcome back to another episode of Startups for the Rest of Us. I’m Rob Walling and in this episode I have fan favorite Ruben Gamez back on the show and we answer some listener questions. In this episode, I actually earmarked five questions that we were going to run through and we only made it through two because we went so deep on these. First question was about optimizing a trial funnel, when to add friction, when that works, when it doesn’t, because Ruben runs two different SaaS companies, Bidsketch and SignWell, and different levels of friction work differently for those two companies. So he has a lot to say on the topic. And then we dive into a question about the core four SaaS skills: dev, sales, marketing, and product. And someone asked me, how do you learn product? So we spend, I don’t even remember, 10, 15 minutes talking through how we learned how to make product decisions. 

Rob Walling (00:54): I think it turned out to be a great episode. Before we dive in, I want to let you know about the SaaS Institute Cancun Retreat we’re having in early December. It’s going to be a two-and-a-half day high-level knowledge sharing event exclusively for seven and eight figure SaaS founders. I know how hard it is for founders at your level to find a group that is at or ahead of them, and this event will be that. You’re the average of the people you spend time with and the SaaS Institute Cancun Retreat is going to be filled with ambitious people who are executing. It’s a small group retreat focused on founders sharing real behind-the-scenes knowledge on what’s working, building relationships, and taking a step away from the day-to-day to figure out the next big-picture move. 

Rob Walling (01:41): It’s going to be at one of the top resorts in Cancun, close to the airport, December 5th through the 7th. And as I mentioned, while this event will be focused on SaaS Institute founders, there is a chance we might open a limited number of tickets to other qualified seven figure founders. You can email tracy@tinyseed.com if you want to get on that waitlist. It’s going to be a great event. I’m really looking forward to it. And finally, if your company serves SaaS founders, we have a few sponsorship opportunities open right now, including this podcast, at MicroConf Iceland, and in our MicroConf newsletter. It’s a great way to get your business in front of thousands of SaaS founders who are actively building and growing their companies. We’re definitely selective about who we work with. We actually turn quite a few sponsors away because we want it to be a strong fit for our audience. 

Rob Walling (02:28): And if you’re interested, reach out to producer Ron, who’s heading up all our partnerships, at sponsors@tinyseed.com. That’s sponsors@tinyseed.com and it’ll go directly to producer Ron. And with that, let’s dive into my conversation with Ruben. Ruben Gamez, back by popular demand. Thanks for coming on the show again, man. 

Ruben Gamez (02:59): Hey, thanks for the invite. 

Rob Walling (03:01): I always love recording with you. It’s fun and informative. So we are going to dive into some listener questions today. The first question, I love it when people do this. Ryan emails in and says specifically, “I have a question for the next time you have Ruben on the show.” And it’s like, anyone, if you’re listening to this, please do that for any guest. You know Derrick Reimer’s coming back. I can get Jordan Gal coming back. I can get Craig Hewitt. I can get Ruben. Anybody who’s been on, if you want questions for Laura Roeder, name someone by name and I will get them on. It’s a great excuse and a reminder because producer Ron told me you haven’t been on for, I think it’s been a year. I think it was June of last year and I was like, “Wait, that can’t be right.” And then I looked and it’s right. 

Rob Walling (03:45): It just goes quick, right? So it’s a good excuse to have you back on the show. And so Ryan wrote in, or actually he sent a voicemail and we’re going to play that right now. 

Ryan (04:00): Hi Rob. I was listening to the latest episode of the Offsite podcast with Jordan Gal and Ruben Gamez and towards the end of the podcast they were talking about friction during the trial flow. Ruben mentioned that friction works pretty well for Bidsketch’s proposal software, but SignWell, his e-signature software, needs to be frictionless. With my own project management SaaS, I have about a two-week trial, but users often need a lot more time than that. And I’ve thought about ways of trying to accommodate this, but maybe it is better for them to contact me than to do a month-long trial or a freemium product. It would be interesting to explore the idea of friction a bit further and even better if you could discuss it with Ruben next time he’s on the show. Thanks. 

Rob Walling (04:42): So Ryan mentioned Jordan Gal’s podcast, Offsite, and he did that for a while but he’s not doing it anymore. He’s now actually on a podcast called The Panel. But he did mention you’re on Offsite and asked about friction versus no friction. So do you want to give folks a little idea of what you were talking about and maybe the difference in funnel, the difference in customer type between Bidsketch and SignWell that dictates what works better? 

Ruben Gamez (05:14): I have two businesses. Bidsketch is proposal software and SignWell, where I focus now, is eSignature software. And I was comparing both of the businesses and some of the differences between them. One of the biggest differences is just this idea of friction: it tends to work better for Bidsketch and not so much for SignWell. They have some similarities and from a product perspective you would think, and even customer-wise a little bit, but they’re very different businesses. So for example, for Bidsketch, we educate upfront. We don’t draw people off into the trial immediately. We do more lead nurturing and all this. I think it helps that business because it’s not just any friction, it’s the right type of friction. If we just added a bunch of form fields to fill out that have nothing to do with anything, or can’t connect to the product, it wouldn’t work as well. 

Ruben Gamez (06:13): But there’s a lot of anxiety around selling and proposals. What do you put into a proposal? How do you price things? So that combined with the time to value being longer on that product, meaning they get into the product and they have to customize it. They have to really think about it. They have to put their offering in there, their services, the things that are specific to them. You can’t guess this, you can’t generate it with AI. And so just that combination of things, with the anxiety, with them not knowing what to do, just lends itself really well to more of an educational, slow approach where we get them a little bit more confident about what they’re doing, why they may want to write things a certain way or price a certain way. 

Ruben Gamez (07:10): And that just works. And anytime we’ve tried to do that with SignWell, even if it’s educational in that way, it’s not worked. We’ve had drop-off because you typically have drop-off when you add friction, but the idea would be that you get more conversions from the people that do come through. For SignWell it’s like consistently we get fewer paid upgrades because of the people that we drop off. I think it’s just a different business because when it comes to document signing and agreements, people are already past that stage generally. If you think about how you get an agreement, you go to a lawyer, draft it up, you kind of scan it and you’re trying to get through it. You’re not that invested, and you don’t have the same anxieties. 

Rob Walling (07:59): I read every word. 

Ruben Gamez (08:00): I’m sure you do. Like the South Park episode about terms of service. Totally. 

Rob Walling (08:08): But that’s what you’re saying. You’re kind of past that and a lot of people are in a hurry at that point, right? 

Ruben Gamez (08:13): Yeah. They’re just in a hurry. They’re trying to get through it. The time to value is very quick as well. They have their contracts a lot of times. So I think that’s what I was talking about. But there are other examples of this. I like Jordan Gal’s example where, you remember when he was getting a ton of interest and signups in CartHook? He added a crazy amount of friction upfront by having an application that people would have to submit. That helped reduce the amount of people that weren’t a good fit, but it also had the side effect of exclusivity, sort of like what they do in courses and things like that. And it worked really well for his product. There has to be a reason for it and sometimes you just don’t know. 

Ruben Gamez (08:59): You just have to try and test some things and learn about your business. It’s not always 100% one way, but most of the time for SignWell, if we just eliminate steps and reduce the friction, it’s going to be better. 

Rob Walling (09:14): I guess you’ve kind of hinted at this, but is it that the time to value is so quick between the two? 

Ruben Gamez (09:20): Yeah. I think that has a lot to do with it for SignWell, and just where they are mentally, what they’re thinking about, what they’re trying to do, how they’re trying to get through it. Those things make a difference. Though I’ll say you can’t randomly add things. There’s something I used in both businesses that worked and was a little random. I learned this from Noah Kagan way back in the day when he was doing contests. You opted in, entered your email address, and then he had a random question like, “Do you like tacos? Yes or no.” Made no sense, totally what you would not want to have on a form. You’d think why add the extra field? Not just that, but why make it a required dropdown that you have to select that’s not pre-selected? 

Ruben Gamez (10:11): And he said it just increased their conversions. So I tested this on Bidsketch first, for giving away templates, and it worked. I have no idea why. And I did the same thing on SignWell except I didn’t make it completely random. I did something like, “Would you like a trial or would you like to hear about something relevant?” And it was better. It wasn’t a huge lift, but there was something there. 

Rob Walling (10:44): And that goes to show you that testing, if you can, if you have the volume, if you make the time, it really is ideal. Because even with all of your knowledge and all of your experience, sometimes you test and it’s just some weird anomaly like, I don’t know why that works, but it does. Can you give us an example? When I think about adding or removing friction I think of SignWell’s signup flow. I could imagine you have a signup flow that’s like: enter your email, and enter it again to make sure it’s correct, now enter your password, now enter it a second time, now we’d like to know your state, and you click next and then enter a credit card, and then you get into the app and there’s some onboarding that shows you stuff. 

Rob Walling (11:38): I’ve just described a very high friction process. What is the quickest path? I think you’ve removed a lot of friction. If I was going to try to sign up for SignWell today, what does that look like? 

Ruben Gamez (11:52): The main thing we have is a Google login button and you can click a link underneath it to sign up with a password, but I want to say like 95% of our signups use the button. It’s crazy. And then that’s it. That’s a really easy signup. And then we do have some questions we added recently, and we were very careful about this because we didn’t have those before. We open you up to the upload automatically because we know that’s what most people want, but not everyone. So we ask some questions to qualify people and put them into two different buckets: like what are you trying to do, whether they’re trying to sign their own documents or collect signatures. And then to understand what they’re trying to do first, like are you trying to set up a template, to direct them to the right place. 

Ruben Gamez (12:44): So that has worked, along with some other changes. But yeah, it’s a pretty minimal process. And then there’s a higher-friction version we’re testing for people with a lot of people in their company, which goes into an onboarding call and a different experience. The bet is that that’s kind of their expectation and they’d actually prefer it. But we’ll see. 

Rob Walling (13:14): But you’re just testing that at this point. 

Ruben Gamez (13:16): Yep. 

Rob Walling (13:17): To summarize: the low-friction signup is I click sign in with Google, there’s an OAuth screen, you pick your email, and that’s it. You’re in. It is literally two clicks. You don’t enter a single piece of information. And then the questions you added come after? 

Ruben Gamez (13:37): Yeah, super fast. So this is another thing with friction. You’ll hear some people say, “Don’t let people with Gmail sign up to your product. Force them to enter their business name.” And a lot of people actually get good results from this. They’re adding friction and getting good results. You think, “Why would you get results? You’re just eliminating the people on Gmail.” But some of those people do have business emails and they enter those instead. So we tried that, making them type in and enter a business email, and we had about 30% drop-off in signups and about a 30% drop-off in paid conversions as well. It mapped super cleanly. There was no benefit whatsoever. But I think to your point, I wouldn’t overthink it with a lot of these things unless you have volume. And in some areas where we don’t have the volume, we can’t go quantitative, so you kind of have to eyeball it, feel it out, and make an assessment. 

Rob Walling (15:13): I think that’s important for people to hear because people try to split test with way too little volume. I did a talk, this must have been about 10 or 12 years ago, it was in Boston, and I was giving a talk about how we improved our onboarding with Drip and how the numbers went up. And one of the first questions was, “How did you test this along the way to confirm the results?” And I was like, “Guys, at the time we were getting 150, 200 trials a month, credit card upfront. How do I test that?” 

Rob Walling (15:56): There was enough gut feel. And then the numbers did go up and I was like, “Cool. I think what we did worked.” At a certain point, in some instances, unless you have volume like SignWell does, you have to go with some rules of thumb, some gut feel. And sometimes you make a little tweak and you do a poor person’s split test where you’re like, “Well, the numbers did go up and maybe I can’t directly attribute it, but my gut feel says that was the right move.” You can’t over-optimize this, right? 

Ruben Gamez (16:26): No, no. Especially the earlier you are. If you have lower numbers, you’re probably earlier, unless you’re enterprise. The earlier you are, the less that stuff matters. You’re not trying to optimize, you’re trying to get really big, obvious wins. And if it’s roughly the same, if you don’t notice a difference, who cares? Do you like it better? Does it align better with your product positioning? Great, go with that. 

Rob Walling (16:53): Go and move on. Yeah. 

Rob Walling (16:55): That’s great. And then do you have any thoughts on Ryan’s second point? He says, “I have my own project management SaaS and I have a two-week trial, but users often need a lot more time than that.” If someone needs two or more weeks to get onboarded, based on what you’ve said, it feels like having a little bit of friction, especially if it’s medium to high touch, is probably the way you would lean without additional information. 

Ruben Gamez (17:33): Yeah. It’s always tough to say. If you have the volume, I would try to look at the data and try to segment out who are these people, what makes them different? But either way, you really just want to find out why. It’s kind of like trying to address the symptom versus the core fundamental issue. You always want to work at the core issue, otherwise you’re just guessing and maybe not solving the right problem. It does feel long. For a project management system, if they’re taking longer than two weeks, the first thought would be, “What’s going on? Why are they taking so long? Is it a product thing? Is it the way that we’re onboarding them, or the expectations they have about transferring all of their projects and their whole team?” Something’s probably going on there. 

Rob Walling (18:29): Love it. Thanks for that question, Ryan. And as I mentioned, if you have questions for Ruben or any other person who comes on this podcast, feel free to send them in at startupsfortherestofus.com or click “ask a question” in the top nav. My next question, I’m not sure where it came from. I either got it on X or someone asked in person because I sent myself an email to my own Trello board. So I’m going to read the question anonymously. The question was: how does one go about learning the skill of product? Because I talk about the core four SaaS skills you likely want on your founding team: development, sales, marketing, and product. Development, sales, and marketing, if you want to learn them, there’s curriculum out there, there are people, you can dive in. 

Rob Walling (19:21): But I think there’s a lot more intuition and gut feel in product. I think it’s harder to learn. So the question was, does product sense just come from experience? If you want to learn more about this, go to startupsfortherestofus.com and type in Brendan Fortune in the search bar, because he and I talked about product, since he helped run product at Drip with us. And Derrick Reimer and I have talked about this multiple times too. Product is also a bunch of other stuff: if you’re at a big company, there’s the politicking, the managing up, the communication to everyone. And there’s also how to build it in terms of where do we put it in the app, what’s the most elegant way to do this. We have these five feature requests that feel vague, we’re not building any of them, but oh, if we just build this one thing, it actually does all five. So there’s some science, there’s some art to it. 

Rob Walling (20:44): When you and I talk about product, to me it’s a very intuitive thing. I hate to say it’s just a gut feel thing, but there’s judgment and taste that I’ve developed over years. And I have a hard time telling people how I learned. How did you learn? You’re good at it. You know what to build. Did you take a course? Did you watch a YouTube video? 

Ruben Gamez (20:57): Yeah. It was a $500 course. No, I guess part of it is also, what do you mean when you say “product”? Because product is so many things. I’ve never really thought about it from, you’re right, it’s kind of like I just know it, it’s intuitive, but that’s not how I got there. Way back in the day, I sucked at product when I first started, same for you. I learned it over time. For me, I learned a lot about product at work, at the jobs that I had. 

Rob Walling (21:37): You were a dev and a development manager. 

Ruben Gamez (21:39): Yeah, I was a developer, but then I also was a dev leader and then ran the web development department. And really anywhere I worked, no one knew anything about product. They didn’t know anything about product marketing or much about marketing. So it was up to me to learn on the way, and it was a slow process. Whenever something came up I would learn and study those things. Like, at some point I got really interested in UX and read several books and then hired UX people who I could learn from and see how they approach things. 

Ruben Gamez (22:35): It was a daily thing: people requesting stuff, us having to weigh what do we have the time for and how do we prioritize this? All these different skills over the years were things I picked up. But then I also was at one point doing some design work, so I learned about design. Coding, design, also had to learn about marketing, like SEO, because nobody else was doing it. So I had to hire and then understand how it worked. That’s slowly over time how I gained those skills. I don’t think I’ve heard how you picked it up. 

Rob Walling (23:21): No, and I don’t know that I’ve talked much about it. When I think of the skills that a mostly bootstrapped founder actually needs, I kind of think these are the only two product skills I have. And so I did okay. I compare this to, if you’re at a big org as a product owner or product manager, you need probably 10 or 15 skills including how to manage up, how to justify your decisions to the rest of the org, how to communicate with the other departments. I don’t care about any of that for a bootstrapped company. The two skills, and they’re different, I’ve known people who are really good at one and not the other. 

Rob Walling (23:59): The first is figuring out, of all the feature requests, everything coming in from support and sales and from your own head, everything that you could build next, how do you figure out what to build? Picking that and having a decent gut feel, prioritizing, building that roadmap of what to build next. That is hard. The other skill is the UX, the design of features. And sometimes that includes, like I said, five feature requests coming in that are all a bit vague and you’re not building any of them, but then you realize: if we just added tags and workflows, it would do everything all five of those people asked for. 

Ruben Gamez (24:44): Yeah. How did that sort of filter down, like from a high level you say “these features make sense because of where we’re going,” but then within that you’re still ending up with a whole bunch of features you could build? I think it’s an underrated thing to manage that and understand how to end up with a good product because you can go into any category and there are products that have all the features and they suck, they’re hard to use. 

Rob Walling (27:43): Yeah. And that’s when it came to a real lean toward more streamlined UX and elegance and saying no to a lot of things, knowing our customers. That was the big thing. I would frequently ask, we’d get a feature request, I’d sit there with Derrick and Ian, one of our devs, and Anna, the customer success person who was bringing it to us. I’d say, “We know we can build this in a couple days, couple weeks, whatever. What percentage of our customer base, or our ICP, do we think will use this?” And we’d talk it through and it was usually a guess. “Is it 5% or is it 50%?” Gut feel. This is the hard part about teaching this. I really had a strong sense of that and I’m not sure why. 

Ruben Gamez (28:41): Yeah. No, we still do that and it is gut feel. You just have to know your customers, know their use cases, really talk to them and understand the different types of customers that you have and what they’re trying to do, how they use the product. But then outside of that, sometimes we build stuff that very few people are going to use because we want more customers of a certain type. We’re like, “We like this customer and we want more of them and we think we can get them.” And that generally has worked for us. It’s risky because it doesn’t mean you can automatically get more of those, but it’s something to factor in. 

Ruben Gamez (29:42): It’s like the two disciplines are UX and product management. Product management is about figuring out what to build. And I’d say you can look into product management communities, talks, videos, and books. But I would completely skip all of the managing up, getting buy-in, and stakeholder stuff. That’s a big part of traditional product management, but what founders are probably more interested in is about what to build, why, positioning in the market, all that. Then on the UX side, there’s very specialized UX, but then there’s also well-rounded UX where “what to build” is actually part of it as well. It’s a little less common, but good UX should entail that. I took a course about six months ago by Shreyas Doshi, I think is his name. I don’t know if you’ve heard of him. Really great product person who worked at Stripe and Google and a bunch of other places. He has great content aimed at product management but relevant for founders doing any type of product work. It’s called Product Sense and it’s a lot of hours, a couple thousand dollars, so it was more expensive. 

Ruben Gamez (30:50): I got it for our product management team and I thought maybe I’ll check it out as well. And I really, really liked it. I think founders would gain a lot from even just watching his YouTube videos. He’s got a lot of free content on YouTube and Substack I think. I like how he described it: you have to decompose it. It’s hard to just take something as broad as “product” and say, “How do I learn that?” You have to break it down. And even things like simulating product experiences, the ability to put yourself in the shoes of your customer, the person using it. You get so much out of that. You can know the concepts of good UX, but if you can’t do that simulation, you’re going to end up with something that’s not that good. 

Rob Walling (31:46): I appreciate that. That’s a really good recommendation. And you know what’s funny is if you were to bring me into a SignWell product meeting and you had a big list of feature requests and you turned to me and said, “What should we build?” I wouldn’t know. My gut feel hasn’t been trained on your customers and your use cases. You know those use cases in a way that I just wouldn’t. It would take me six months or more to get there. I think of it in a way, I’m going to do an analogy. Do you play an instrument? Guitar, piano, anything? 

Ruben Gamez (32:23): No, I’ve played a little bit, but not too heavily. 

Rob Walling (32:27): So I’ve played guitar since I was in college. When you first start out, you’re basically trying to read a chord. It’s like the G chord. You put this finger here and these fingers here and it’s just so hard to do. And then you play it and it doesn’t sound good. Then it’s like, all right, now switch to a C and you’re like, “How do I do this?” It takes you two minutes just to move your fingers. And then you go to a D and it’s just this agonizing thing. Well, you do that a thousand times and I can now literally pull up a guitar tab of any pop song and sight read it because G no longer means I have to think about it. G just means this. It’s muscle memory because I’ve played the G chord probably 10,000 times. 

Rob Walling (33:07): So the ability to sight read, I feel like if we were in a SignWell product meeting, you would sight read. There would be all the input going in and you’d just know. And I’d be like, okay, let’s think about this use case, I’m trying to figure out how to play this chord, I’m trying to understand your customer. So there’s a certain amount of repetition and understanding and practice. It can translate from app to app, but just because Derrick and I were good at product at Drip, I wouldn’t automatically be good at product at SignWell. It would take a huge learning curve, and I want people to understand that too. 

Ruben Gamez (34:07): Yeah. It can take some time, but it can actually go much faster than I thought before. I experienced this with a product person who had been a fractional chief product officer for many years, and had done his own startup and helped at some well-known startups. He came in to help us and it was really amazing to see how quickly he built his product sense for our product and our customers. There were no shortcuts. He went through so many feature requests one by one, reading the actual words, asking us questions. Very grindy work. But after going through all of that, it was a crazy amount of information to process, and I could just see, yeah, he started to give suggestions and ideas and I was like, “Actually, he’s pretty good already. He gets it.” So it can be done, but you need to have that repository of customer information. Otherwise you’re learning it as it’s happening. 

Rob Walling (35:31): I like this because I’ve never had to jump into a product cold and make product decisions. With HitTail I acquired it but there was an existing user base emailing me, and with Drip we built it from scratch from day one so every feature request kind of went through our heads and all added to the filter and the gut feel. Well, sir, thanks so much for joining me on the show. That’s all we have time for today. I have a couple listener questions earmarked for you, so I’d like to have you back in the next few months. If folks want to keep up with you, you are @earthlingworks on X/Twitter, and of course the best electronic signature app on the internet is signwell.com. 

Rob Walling (36:19): Thanks again for joining me. 

Ruben Gamez (36:20): Thank you. 

Rob Walling (36:22): Thanks again to Ruben for coming on the show and thanks to you for listening this week and every week. This is Rob Walling signing off from episode 837.