Ruben Gamez: Land Clients with Your Proposals and Launch a Competitive Spin-Off | SaaS District

In this SaaS District episode, host Akeel Jabbar interviews Ruben Gamez, founder of Bitsketch (proposal‑design SaaS) and DocSketch (electronic‑signature SaaS). Ruben recounts his early career—from running a small web‑dev shop (9th Sign) to managing a development team at Oasis Outsourcing—before spotting a gap in the market for a dedicated proposal tool. He left his corporate job after his side project generated enough income, choosing to stay bootstrapped despite investor interest because he valued freedom and low overhead. Early growth relied on outreach for reviews, content‑marketing, SEO, low‑cost AdWords, and strategic integration partnerships. He experimented with pricing models, initially launching a freemium plan that stalled conversions; removing the free tier dramatically improved paid sign‑ups. Drawing on data from analyzing over 25,000 proposals, Ruben shares best‑practice insights: keep proposals short (around five pages), bundle fees instead of line‑item pricing, and front‑load value‑focused pricing information. He then explains the discovery of DocSketch, noting the larger e‑signature market, the challenges of competing with incumbents like Adobe Sign, and the strategic choice to target underserved segments and leverage unique acquisition channels. COVID‑19 shifted demand—proposal traffic fell while e‑signature usage surged. Ruben highlights “engineering as marketing”: building simple free tools, SEO‑driven lead funnels, and continuous traffic generation as growth hacks. Finally, he discusses managing both products with a lean support model and outlines his excitement for expanding DocSketch in the latter half of 2020. The conversation offers practical lessons on bootstrapping, product‑market fit, pricing, proposal design, and growth tactics for SaaS founders.
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Hello, hello everyone. This is your host, Akeel Jabbar, and welcome back to another episode of SaaS District. In today's episode, we'll be talking about how to land more clients with your proposals and how to launch a spinoff product in a very, very competitive market and gain traction. Today we have our guest with us, Ruben, joining us from Bitsketch and DocSketch. Ruben is a specialist in bootstrapping, marketing, user experience, and software development. He is now the founder of Bitsketch, a professional web app focused on designing, tracking, and customizing proposals in no time. In the past, previous to working at and founding Bitsketch, Ruben owned 9th Sign, which is a small business specialized in web development and consulting. After that, Ruben worked at Oasis Outsourcing as a web development manager, which is the largest privately held PEO at the time. Then Ruben decided to quit his job and found Bitsketch, where he's grown it and improved it since 2009. And recently, about a year ago, he founded DocSketch, which is an electronic signature tool. So welcome, Ruben. Glad to have you on our show today.
Thanks. Thanks for the invite.
Yeah. So I want to get into it. You started with And running and operating your own company at the time, which was 9th Sign. What happened that led you to leave it and start working at Oasis Outsourcing as a manager there?
Well, I don't— it was never a full-time thing for me. So it was, it was really something that I created when I was learning to design websites and to code up websites and stuff like that. So I needed something to, I guess, a company to have money and checks written to whenever I was sort of like practicing by building sites for friends and, you know, other people that I kind of knew. So it was more, I think the whole, even thinking about it, I think the whole goal of it was to have something that I could put sort of like a portfolio Portfolio of sites, some examples, some of them real, that I could use to get a job being a developer. So the whole goal really was to get a job being a developer.
Mm-hmm.
Just a little strange because now that I think of it, for some reason I never even considered like, oh, maybe I should just, you know, continue down this path and just grow it to where this is what I'm doing. Instead, my job was— my goal at the time was to get a job.
Makes sense. And then where did the idea of Bitsketch formulate from at that time? And is that when you made the move to quit your job and focus to grow it?
Yeah.
Start up on a full-time basis?
Yep. So I was at— this was like many years later. So I'd gotten the job, you know, and then I was hired as a developer. I got promoted several times, eventually ran the whole web development department, had teams of, you know, people. And then I just didn't like what I was doing. I found out that I was no longer doing the things that I wanted to do. I didn't like management in that sort of company generally, so I started looking for I started reading blogs and books and things written by people, content written by people that had started their own products, SaaS products. Usually back then were even like shareware products and things. It was really fascinating that somebody could, some of these part-time, some of these full-time, just build their own thing and it was often just them. I thought, wow, I want to do this. I was looking for something. to build. And I had started building another product, but I remember it was nights and weekends and just being bored. Like, I didn't like the— there was a need there.
Yeah.
But I didn't like the space. And one day somebody at work was going to have a client meeting for the very first time, and he asked me about proposals because the client asked him to bring a proposal. And I thought, well, just to make it easy, just go online and find a template. So I searched for templates, you know, that was easy enough to kind of find. And I thought, you know what, you should just use something like FreshBooks but for proposals. So then I searched for that and I couldn't find anything.
Hmm.
It's weird. How's there not this thing here? This is crazy. So I searched, searched, couldn't find anything. I just referred them to the templates and they got me thinking like, wait a minute, nobody's built anything like this for proposals. This is nuts. And that sort of kicked me off in that direction. I built that nights and weekends, grew it for about a year and a half, and then it was enough to replace, you know, a good portion of my salary and quit the job and just go off in that direction. And I've been doing SaaS products ever since.
Nice. So it was that pull to quit was just based on, you know, having enough income. You've already built that bridge, so to speak. It wasn't You know, I'm leaving, I'm just going to go focus on this. You had something to jump towards, and you had that confidence to make that leap at the time, right?
Yeah, yeah, and motivated. I really didn't like what I was doing, and I wanted to do something different.
Right. What was the decision to remain a bootstrap company at that time? So you had some traction, you were— you had some funding, you had your job to pay your bills, and you also had money from this new venture. You know, you could have went to, you know, VC and said, hey, like, you know, can you fuel this and help Grow the company. Why did you decide to stay at the Bootstrap?
Yeah, I actually had it very early on. I had an offer from actually the person who, who asked me advice for, for the client proposal. His, his, his father was a doctor or something, and, you know, I'd met him previously, but then I guess he had told his father, and his father was very interested in investing some money, and I, yeah, I turned it down. I'm trying to think of my thinking back then and why I was not that interested. And throughout the years, I had other people interested in investing, some well-known internet marketers and other people that I'd known. I didn't need to. The business was growing. well. I didn't feel like I was stuck, or I didn't feel like a lot of money would have helped in, you know, helped our growth in any really specific way that I could think of at that time.
Mm-hmm.
And really, I was taking— I was doing business like differently, right? The whole goal of business for me at the time was freedom. And that, that kind of, I felt like that worked against that in some ways. So what I did was when I quit the job, I worked very little. I worked, you know, there was a good period of time where I worked just like literally like 2, 3, 4 hours a week and just took money out of the cash out of the business and, you know, all this. And even when I returned back to work, I worked very little. I don't think it was It was, I think it was bad for growth. It definitely was bad for growth for the business, looking back at it. Um, but I felt like that was the thing that I needed to do or wanted to do at the time for, for a while.
Got it. So you built it more of as like a lifestyle business at the time. And obviously without any accountability, you're probably burnt out from like management and people breathing down your neck to do anything. You said, I've got money, I'm going to do whatever I want to do. And yeah, if you did take cash at that time, you're now accountable. To that cash, and now you have responsibility, and you have to deliver on what you say you will, right? So yeah, that makes sense. Right.
And I was taking, you know, take $10,000 here, $30,000 there, you know, just these chunks of money out of the business every once in a while. Hard to do when you have investors, right? And right, you can't really be doing that.
Exactly. So can you tell us about, you know, early days when When you first started Bitsketch, so you were working this on weekends and evenings, what growth strategies worked that you've applied at the beginning that led to that growth at the time?
So at the time you could go around, you can still do it a little bit, and ask people for reviews. This was a strategy that I used that I saw Peldi from Balsamiq Mockups do, and he had blog posts written all up and even a template email and stuff. I thought, well, this is great. Let me go out and do this. And I did, just emailed a bunch of blogs and stuff. And I didn't really get picked up in very many places at the beginning. I did get picked up at like About.com, which was more of a thing back then, and launched with partially that strategy. And then later on, it took like a couple of months, like for some reason a couple of them started to, you know, I don't know if it's like, oh, they're finally getting to the email or something, but Yeah, sure, we'll review it. And then they added us to— and that kind of led to some— once a couple of bigger blogs sort of did that, it led to other blogs and it was like this whole domino effect, which gave some pretty decent word of mouth and traction very early on. That along with content marketing, SEO, which I was very much experimenting with and to where I thought, this is crazy. You can find keywords people are looking for, write content, and people will come visit you just like that. Nothing else. Just like that.
Yeah.
So then I remember writing content, trying it out. 2 weeks later, started getting a little bit of traffic and I was just blown away and just did more of that. AdWords, remember getting like 10-cent clicks. It was easier to get clicks for cheaper back then. And integrations, a lot of marketing through integration. So that strategy was more— before we built out integration, I'd go out and I'd talk to somebody. Yes, we're thinking of building a CRM integration. So I wanted to check in. What do you do for integration partners? What can you do?
Mm-hmm.
This was before building out the integration, just checking who's in charge of integrations for your company. And then negotiating that early on, and that was more likely for them to do extra things for us to try and get us to prioritize the integration for us to build. And that was helpful as well.
Cool. So I know that leveraging other people's audiences, that really helps, right? They already have the audience, just getting your face on there, getting that review. That's funny, we actually had Peldi from Balsamiq on an interview, I think last week, so we'll be launching that pretty soon here.
Oh yeah, nice.
Funny timing. He's an awesome entrepreneur. Yeah, he's great. Yeah. Okay, so some SEO, some Google AdWords, and then some integrations, you'd say, kind of what led to that early growth. Cool. So equally, or even more important than what worked, and a lot of people don't share, is what didn't work and what the failures you've achieved. Can you share some failures, whether on marketing or product, whether that's within Bitsketch or DocSketch today, and what they've taught you to become a better entrepreneur?
Sure. So, uh, with BitSketch, we launched with freemium, and, uh, when launching to the list, people bought and it was great. But then just after that period, which was, you know, very short, 1 to 2 week period, I remember exactly how long, um, just getting traffic coming in and trying to sell to that traffic. It, almost nobody bought. It was, it slowed down to like launch day, the first 3 days or something like that. We had 22 people, I think, buy, right?
Mm-hmm.
And the list was really small that I had. You know, I was just getting started. So it's not a ton of people, but for me it was a lot of people. I didn't expect to have that many. And then I expected like, okay, great. Like this is just in 3 days, you know? Yeah, it's a launch, so maybe you'll slow down a little bit. Let's say 20 people a week, maybe, you know?
Right.
And what really happened was that 1 person a week ended up buying at that point. And I remember trying really hard to increase conversions and doing all this stuff to try and get more people to pay. And I didn't know what was happening. I didn't know what was the problem. And why it was so different. And then I got rid of the free plan at some point. And suddenly, just, you know, I don't remember the exact difference, but it was like night and day, just started getting a ton of people paying for the product compared to that.
Right.
It was still, you know, smallish in scale and stuff, but it was significant and very encouraging and like, okay, we have something here and I can build on that and grow that. So that was one thing that was very surprising and I had trouble with early on. For DocSketch, funny enough, we launched with freemium last year and we're still doing freemium now and it's working pretty well for us at this point.
Wow.
But there are a lot of different reasons for that.
Right, so it depends on the product market, whatnot. Do you still have a free trial or you just went, just paid around everything?
Free trial for BidSketch.
Yeah, okay, and that helped you find?
Yes, yeah, that was good. We did a lot of testing with that, a lot of price testing too. That was a great lever.
Yeah, so I want to talk a little bit about the BidSketch for a minute here. So I know you focus on this proposal software. Platform to help agencies, you help freelancers, consultants, sales team to help them close deals in a better fashion, which you couldn't find at the time when you were working at the agency. So I know you guys did research, whether yourself or your team, on over 25,000 different proposals worth, I think, $270 million to find the key differences between winning and losing proposals. What trends or tips can you share to SaaS sales executives or founders to improve their chance of closing Deals? Like, how do they find more, you know, close more deals?
I think one of the main things is that you need to get more people to actually read your proposal or read more parts of your proposal than often happens. The reality is that, and often it's equated with the larger the deal, the more pages or content, the bigger the proposal needs to be. But the data showed that regardless of amount, the shorter proposals often did better. And we have data for, you know, how long people spend on pages and how, you know, how much they're reading the proposals. And usually all of it correlated with just like smaller, tighter proposals just getting more engagement and doing better when it comes to landing deals and closing sales. The payroll company that I worked at before I started Bitsketch, they did essentially just like a couple of page proposals, and that's what they used to land million-dollar-plus deals, right? Like, it had nothing to do with, you know, this is a million-dollar-plus deal, let's create a 50-page proposal. Nobody's gonna read that.
Right. I think it's just government, maybe they need that for like documentation and following up. Right, right.
In certain very specific industries, yeah. But yeah, generally Generally speaking, no, it's not needed. The other thing is the bundling of fees is generally better and does better than doing like line item, almost like invoicing style, you know.
Okay.
There are a lot of problems with that style because it invites people to go in there and do analysis on like, hmm, why is this this many hours? Can we take this out of the thing? Instead of like focusing on like, what is the value of this proposal, right? What is the goal that we're trying to achieve and attaching a price to that?
A total price, a final price, combine all those services, line, line, line, here's the final price.
Yep, exactly.
And that first piece, how many pages are we talking about? 5 pages, 10 pages? What's short? What did you find is sweet?
Yeah, like 5 pages. We found, we looked under there and I think the 5 pages was In that range was what we saw that did the best.
Wow. Including cover page or you just skip that?
I'm trying to think of if we— good question. It's been a while. It might have or might have not, but it was pretty close. Like if you go up 6 pages or if you go down 4 pages, it was still right there in that spot.
Cool. Anything else you think you'd say? So, you know, bundling, uh, you know, size, anything else?
Um, the people that do the best, and this is, uh, based off of just our— the experience in the market and with people that close really big deals and have a much better closing percentage, because, um, we've, you know, we've talked to and seen companies that just close a lot of their proposals versus ones that hardly close any. And when you look at the more extremes, what's going on there and what really helps proposals close is that the ones that are doing the best basically almost have a yes by the time that they're getting— that the proposal is sent, right?
Mm-hmm.
Versus the other ones, it's— they're trying to do all of their selling in the proposal and they're trying to have that, You know, which is— it's not— if you think of it more almost as the closer you get to that yes, and the closer you get to like, this is almost like a summary of the conversation that we had, right? Then like the better that your proposal is going to do.
So focus on the actual sales pitch. So that's just complementary to just close the deal at that point.
Right.
Yep. Can you speak about— I just want to get a little deeper on that. What are some key details founders should use to say wow their customer in that proposal? What is that 5 To 6 pages include? Because I see people include, oh, I need to put 3, 4 case studies, I need to put all these logos that I worked with, I need to put, uh, like you said, they're explaining everything, who we did, you know, uh, pricing, about us, about our service, uh, here's some blog posts, right? They just go on and on about me, about my family, right? And then, okay, here's the price. What's it?
Yeah, it really should be about the, uh, the, the, the client and the customer. The very first thing in the analysis that we saw is like, what do people look at first when they go into a proposal? And the very first thing that they look at is they go down and skip all the information, usually generalizing here.
Yeah.
All the information about like, yeah, we do this and blah, blah, blah, we're this, or even, you know, you came to us because of this, or we've worked with these customers and You know, what they do is they scroll down and they go right to the pricing.
Yeah, yeah.
Right? So that, that, that, that section is just key, is really key for it to be— it's not an afterthought, it's literally the very first thing that most people scroll down to and look at. And it's not necessarily about what the price is, but what they're getting for that price. and how you're framing that, right? And are you talking about the value there that you're delivering, or are you talking about some asset or delivery in a more project management sort of way, right? There's a difference there.
Exactly.
And then the other sections that they look at is they're about what do you do for us, you know, what are you proposing for us? What are you offering? What are you, what are you saying that you can deliver to us? It's not the stuff at the end, like, um, we've worked with these clients and all that stuff. That's generally, that's last.
Hmm. Okay. So this is the price. This is what we're going to do for you. And this is how maybe, you know, what results we think we can get for you. Probably that's maybe as—
And why, right? Like believable.
Yeah. Makes sense. Okay, so at this point, you know, you built Bitsketch, you have this vision on building it, you know, 9 years now or plus. Can you tell us the discovery and the opportunity of DocSketch and how did that come up and formulate over the last year or so? Sure.
So we had— DocSketch is an electronic signature tool. So it helps people get their documents electronically signed. And in Bitsketch, we have electronic signatures, but it's a very simple workflow, right? So we integrate with, with tools, with electronic signature tools, and we had been asked to integrate with electronic signature tools. And we started getting asked to not just integrate with those tools, but to it into Bidsketch. And the more we looked at it, the more it was obvious that this is a whole category. Like, there's overlap there because we have electronic signatures and proposals, but it is literally— it's a huge category, much bigger than the proposal category. And we thought, you know what, we should really build a product in this space. There's something— we have some customers that are asking for it. There's some good overlap here. The market is bigger. This seems like the next natural sort of stage. The things at the edges related with, with your product, you know, like that you usually integrate with, sometimes can be really good targets for like a second or next product. So that started off in that, in that journey and we built it out. And now that we're into it, we are seeing that there's some overlap there, but not as much as we thought. And it's a very big market. It is super competitive. Yeah. For a reason though, because it's a big category with a lot of buyers.
Yeah. And adding to that, so how do you make sure DocSketch remains competitive against companies such as Adobe EchoSign, HelloSign? There's a couple of big guys in the space, right? How do you compete with them?
It's really hard to compete with, uh, um, it's really very old established companies that have been in the category for many years, have a ton of features, and just go out there as somebody new with a much smaller team and just build a product with less features, um, and less word of mouth and just be competitive and grow that, right? So oftentimes There's multiple approaches people take to make that happen. One of the more popular approaches is just to narrow down the focus into a key segment of the category that's maybe underserved and then focus on that and, and basically serve those customers better and gain traction there, word of mouth, and sort of expand slowly. I found That's one of the options that I evaluated and did some testing around that initially. Didn't find too much traction that I got excited about in that area. The other is basically owning a channel or category or discovering, you know, something on the marketing side, some way to acquire customers that in a very competitive market, will be a meaningful, you know, whether it's like partners, right? Because, okay, we have these partnerships that nobody else can have, or we can do this type of marketing, or there's an opening here for us to, on the marketing side, for us to acquire customers this way. And that sort of— I found several things that appealed to me in that direction. So that's the approach that we took.
Okay. Any trends that you guys are seeing right now in terms of volume for whether it's e-signature proposals going out during, you know, COVID situation? Any specific industries that are seeing higher activity if you guys are analyzing that?
Yeah, it's really interesting. For— so for Bitsketch, it's been— it's actually been lower, like agencies and freelancers.
Okay. Yes.
Yeah. It's more— it's getting back to normal now, but for especially the first few weeks, it was It got really low, and I think they got hit hard. So the activity level was low. For DocSketch, it was the complete opposite because people were forced to work remotely, and some of these companies, you know, needed to— needed to— they couldn't do paper documents anymore, so they had to get them signed digitally. And for many of them, especially that we're talking about, we're We're bringing on board like 30 to 50 person teams that have had this on their list for sometimes years. Like this is, you know, this has been a priority or not enough of a priority and now finally we're gonna do it. So we're seeing a lot of that for some of these businesses.
Cool. And were you targeting your own list or you built this product and you went out and you started to market it?
For DocSketch?
Yeah.
Yeah, we've not mentioned it or marketed it to the BidSketch audience. So we literally started from scratch, right? Like put up a website, zero visitors, nothing, right?
Wow, okay.
And didn't— it was planned, but once I saw that there was less overlap, it was like, okay, let's focus on the things that are gonna give us the more ideal customers. So that's, yeah, from launching last year, you know, I think I mentioned before, it was just a few thousand visitors a month, a couple hundred signups a month, to this year, it's like we're at 350,000 uniques a month, visitors, and 10,000 signups a month.
So I'm gonna Dig deeper there. I know I'm gonna be mindful because I know it's a very competitive space. Can you share any unconventional growth hacks that maybe many founders don't think to use that's well— that has worked well for you guys at DocSketch in the last year? Because that's a pretty quick growth, right, in just a year or so?
Yeah, yeah. So I would say tools, marketing with tools, engineering as marketing is something that's been really helpful, and we have more that we can do in that area that we'll probably be looking at. But that can be a really good channel. Like, a lot of people think of HubSpot's Website Grader and stuff like that, and sometimes they'll build out tools and like a mortgage calculator or something.
Yeah.
But what a lot of people are missing is that they're missing that ongoing— where's that ongoing going traffic. Like, yes, you can launch your tool and get like a little bit of buzz, and then what happens? What are you going to do with it, right? So there are different— it's super, super, super, super important to think about that. And either you're building a tool because it's easier to market your product with your tool, right? Meaning like HubSpot. There's certain products that are kind of hard to explain, hard to get into.
Yeah.
But if you can give away a free tool, this is easier. We can, um, we can acquire customers with the lead by leading with this tool. Um, or there is existing demand that is asking for this free tool and we can build this and that aligns really well with our product and we can just, you know, flow them into our product after we get them on board. So there are multiple approaches with that. Um, and, uh, yeah, basically it's work backwards.
Mm-hmm.
Not just the tool, but how are we going to— so how are we going to turn the people who use this tool into customers and where are they going to come from on an ongoing basis every month? So we've used an SEO strategy for that, looking and exploring sort of like keywords and seeing where demand is and doing it that way. You can look at somebody like Brian Harris from Video Fruit. He does a lot of courses and stuff like that, but what's interesting is that he leads with free tools, which is very different, especially in that space. And they do— they use paid ads for the tools. So the funnel, how those funnels work is that the tools are almost like—
A lead gen, right?
Yeah, right, exactly. They're almost like ebooks, right, on steroids. And you get the cost per acquisition is low enough that it makes the whole funnel work when you bring in people into the free tool and basically upsell them to your main products.
Nice. So you built this tool, now you get— it's about getting it out there. So that's an interesting marketing strategy. I know a lot of people talk about it, but I know it's So it can be risky too, right? Because you can build those products and it's free. So you can drive free traffic, you can do SEO. So you can think free e-signature tool, you can think free widget. I won't get into that, but specifically, and then I find it, then I start playing with this tool and then that leads you, you get their email, you get their information, and that possibly leads to finding out about your product in a, or maybe a more natural way.
Exactly. But it has to be a simple enough tool to where you're not suddenly building 2 products, right? Because it's hard enough to build one product. It's got to be like a small enough, simple enough thing. So it's challenging to find the right thing, but it's, it's not as hard as people think.
And I guess now at this point you have Bitsketch and DocSketch. How are you managing those 2 things? Are you kind of just, you know, Bitsketch is on the side and you're putting that and letting it run on its own with the team in place, or, and you're focusing on Desketch? Are you trying to balance both?
Bitsketch, both of these products are really low support product. products. Meaning we're getting a good amount of people signing up and leads and customers and all that stuff on DocSketch. And it's easy enough for one person to support both products.
Okay.
And still have time left over on the support side, right? So it's actually not been very hard, but I have friends who have products that, you know, You know, have a fraction of the paid customers and users using it, and they have like support teams that are like constantly busy. So it really depends on the product type, the market that you're targeting, and various other things.
Right. If you had enterprise sales guys, they'd be going out. You have to manage them to go out and sell big-ticket items, right? So it makes sense.
Exactly.
So yeah, last question here, I guess, you know, What are you most excited about the second half of 2020? And where can our audience get in touch with you? Sure.
So really just working more on DocSketch, expanding what we're doing there, looking to do some big things in the electronic signature space there. I think there's some interesting opportunities of just making the whole process of getting documents signed easier, faster. And that's really where the focus is going to be And doing some interesting things too on the acquisition side and maybe free tool side, some more of that.
Cool. Look forward to seeing that. Where can our audience get in touch with you if they want to learn more?
Sure. Either DocSketch.com, BitSketch.com, or on Twitter is where I probably spend too much time on sometimes. And that's EarthlingWorks over there.
Earthling Works. Okay, awesome. Thank you so much, Ruben. So guys, check it out, DocSketch. We'll leave it in the show notes as well, and Bitsketch. And thanks again for being here. Appreciate it.
All right. All right. Thank you.
Thank you all for listening in to today's episode. Don't forget to join us for another episode where we interview top leaders and experts in the business and SaaS industry. If you enjoyed this episode, I ask that you please give us a 5-star review review on iTunes. That would be really, really appreciated. Otherwise, if you have any feedback, suggestions, or improvements for this podcast, please feel free to send it directly to me on our website at horizoncapital.com, or you can just tweet me @akeeljabbar. Thanks again, and hope to see you guys on the next episode.
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