Getting a 7-figure-ARR foothold in a crowded market

While growing his first product, Ruben Gamez, saw a gap in the e-signature market. After lots of market research, he identified a way forward, built a simple MVP, tested it with customers of that first product, and then expanded into the gap.

Now, SignWell is bringing in several million in ARR.

Here's Ruben on how he gained a strong foothold in a crowded market. 👇

The early days

I’m the founder of SignWell, an easy-to-use electronic signature app that helps thousands of people get their documents signed legally and securely. We generate several million in ARR, have tens of thousands of paying customers, and are growing fast. We have processed over ten million signed documents, both through one-off sending and automated API workflows like SaaS companies embedding e-signature functionality into their platforms and products.

I got started in tech later than many other founders. I didn’t have a computer until my 20s. I didn’t even know how to turn on a computer. I learned to program before I owned a computer by reading a book on C++ and writing code with paper and pencil.

Once I got into tech and my first office job — tech support for Compaq computers — I met someone at work who told me they had their own website. I was blown away and asked him how he did it. He showed me a website called webmonkey.com that had a bunch of web development tutorials. I went through those tutorials and taught myself web development, design, and even some animation — shout out and RIP ActionScript/Shockwave.

Eventually, I hustled to get a job as a ColdFusion developer at a large payroll company. This was my first real dev job. Here, I learned other web development languages (ASP classic, Java, Python, Ruby, etc.), UX, SEO, and a lot more.

Several years later, I decided to launch and bootstrap my first startup, and now I’m on my second one with SignWell.

Starting with market research

The idea for SignWell came from customers of my first SaaS, Bidsketch. Thousands of paying Bidsketch customers asked for better e-signature options than our integrations offered, prompting my initial market research.

I tested the market to see if demand existed beyond what Bidsketch customers showed. Many complaints highlighted the expense and difficulty of existing e-signature tools, so I saw a product opportunity to create something with modern, intuitive UX, that was more affordable, and highly secure and compliant.

And a couple of interesting distribution opportunities were unexplored, so I saw a path to acquiring customers. The e-signature market is crowded with many options. Part of the puzzle in markets like this is cutting through the noise and reaching the right people—customers and partners.

A wildly basic MVP

The first version was interesting because it was very basic compared to our current product. Users could upload and sign documents, so it performed the core function, but we lacked several features one would consider essential for launch.

For example:

• Audit trail

• Template links

• API

• SOC 2/HIPAA

Looking back, it's wild to think we launched without something as core as an audit trail. Early on, we manually generated audit trail reports on demand, which was enough for customers while we properly built the automated version.

We now have all of this (and more), but none of it existed back then.

Currently, we’re using React, Rails, Redis, Sidekiq, and PostgreSQL, and we run everything on AWS. For SOC 2 and HIPAA, we use Vanta, which cuts down on some of the work, but managing that still involves a fair amount of overhead since we’re SOC 2 Type II in three categories — not just one, as companies typically do.

A tough market

When I first started considering building an e-signature product, I talked to other founders and marketers who previously built in the same market. Some exited successfully, while many others did not. They all said the same thing: "Don’t do it."

Obviously, I still did it, but now I understand what they meant. The market is difficult. In a mature and crowded market, you can’t just build another e-sign product and expect fast growth and customers. You need both distribution and a unique product angle.

Figuring out how and where to compete took a lot of work. While Bidsketch customers were a good starting point for early feedback, I needed to find people who already paid for e-signature products and weren’t happy.

To learn from customers of my competitors, I ran ads on Twitter, targeting competitor audiences and offered an Amazon gift card for a 10-minute call about their experience with the specific competitor they used. I also created an early access homepage that redirected sign-ups to a survey asking about their experience with existing tools, then redirected them back to a confirmation page for early access.

Our product differentiation is enterprise-grade features and compliance at an affordable price, with a nice UX and developer experience for the API. It took several years and a lot of grinding to get here. From an opportunity-cost perspective, easier markets exist. It took a lot of work and time, but today, we’ve built a brand people like and have significant market traction.

Cheap but secure

We’re one of the few e-signature products that still offer unlimited documents. All older, bigger brands did this originally, but they moved away from this model and adopted aggressive pricing tactics, locking you into long-term contracts.

We offer free documents with our e-sign API, but for higher-volume use, we charge a low per-document fee. We’re typically 5x more affordable than competitors on this front.

That said, you can’t be more affordable and expect to win in a market like this. None of that would mean anything if we didn’t have an extremely high bar for security and compliance. We handle a lot of sensitive data, so it’s a must for many of our larger customers. And many cheaper competitors can’t or won’t do this.

This isn’t an easy combination to achieve, but it has helped us gain good traction and grow revenue.

Indirect distribution

As far as growth, every stage has been different.

Going from 0 to 1 and getting those early customers involved finding traffic and leads any way I could. I initially experimented with indirect distribution and ads (Google/Facebook).

Indirect distribution was the most helpful strategy. To acquire customers, everyone targets the most obvious leads, like people searching for e-signature products. But I’ve found success in crowded markets by targeting related solutions that lead to my product, which competitors ignore.

For example, when I got into the market, I grew traffic to over 100k monthly visitors by creating free contract templates. This is indirect because we don't create contracts; we help sign them. But I knew that people who download contracts would then need to sign them.

No one in our market was active in this space at the time, so it was a good opportunity to offer something free to potential customers.

Back then, I also created a Google Sheet listing our “Dream 100” places to get mentioned and partner with. This is a strategy from the book, “The Ultimate Sales Machine.” You create a dream list of important partners or customers, brainstorm an angle for each, and contact them personally, one at a time. Relentless follow-up is part of the mix.

More recently, it’s involved a mix of many different things, from sponsorships and partnerships to integrations and building features to bring on larger teams and enterprise customers. 

Learn from people in your market

Here's my advice: Learn more aggressively from people already in the market. Everyone does this to some extent, but most people can go much further.

For example, I found e-signature startup founders and marketers, and learned from them. I didn’t know any of these people when I started. I found some by listing launched products in the space, checking their status, and then using LinkedIn to contact former employees.

I also spoke with at least ten sales reps from e-signature startups. I even had weekly and monthly consulting calls with one of them; he shared how he sold into the market and discussed specific scenarios I faced.

Beyond that, it's crucial to become good at doing uncomfortable things. You'll most often find the most growth — both personal and business — by doing things that initially feel unnatural or uncomfortable. Eventually, it gets easier if you keep going, and the payoff is well worth it.

What's next?

On the business side, I want to deliver a great product, grow an amazing team that serves a market largely abandoned by established brands, and build a great brand.

On the personal side, I’m entirely focused on my family and on raising our two kids to be healthy and happy.

You can follow along on my X. And check out SignWell!