Ruben Gamez expanded from proposal writing into e-signatures

A Second Business That Led From Proposal Writing to E-Signatures

Ruben Gamez grew the proposal service Bidsketch, then developed the e-signature feature his customers had been asking for into a separate product called SignWell. In an Indie Hackers interview published on January 14, 2026, he said SignWell is earning millions of dollars in annual recurring revenue (ARR). He did not disclose the exact amount, and the figure represents the company's recurring revenue scale.

Proposal Software Started While Holding a Day Job

The idea for Bidsketch came while helping a friend who had started freelancing. The friend needed to submit proposals to win web design projects but had no experience writing them. When Gamez looked for tools, he found an old installed product that worked as an add-on to Microsoft Word, and a web-based alternative like the one he wanted was hard to find. After researching search demand, he confirmed the potential of offering this work as an online service.

The problem he chose was the copywriting, editing, delivery, and follow-up that repeat every time a proposal is made. Bidsketch let users combine descriptive copy, price items, and design to build a proposal, deliver it through a per-client page, and check whether the recipient had opened it. Reusable content reduced the burden on freelancers and agencies of building documents from scratch every time they met a new client.

The product launched in October 2009. At the time Gamez was working at a payroll services company and ran development and marketing alongside his main job. He outsourced part of the development but also went through trial and error in ending relationships with three developers. Even though he started as an independent founder, he did not carry out all the production work alone.

Before building the product, he opened a landing page and a blog to gather potential customers. He wrote posts on topics people searched for, offered proposal templates, and emailed more than 30 bloggers asking them to introduce the product. The response rate was low, but the few bloggers who did introduce it brought in early visitors and signups.

His attempts to build free tools sometimes failed. He spent about six weeks building a free quote calculator to bring customers to Bidsketch, but once the interest right after launch faded, almost no visitors remained. From this experience, Gamez learned that free products also need ongoing promotion and search traffic.

He decided to quit his job only after the business had grown enough to support his living. In a September 2011 Mixergy interview, he said he had about 850 paid accounts and that the previous month's revenue had been a little over $10,000. He described the operation as still a one-person business at the time, and recalled that, having already secured enough revenue, he did not feel much anxiety about making a living when he decided to quit.

A Period of Learning About Purchases and Retention Rather Than Visitor Numbers

As it grew, the way he acquired customers changed too. In addition to blogger introductions and search traffic, he used integrations with other software and cross-promotion with products that had a similar customer base. Customers who came in through integrations, in particular, were smaller in number than blog visitors but showed better results in paid conversion and long-term retention.

He revised the pricing page each time the customer mix changed. Early on, plan names that reflected a customer's profession and business type, like Freelancer, Studio, and Agency, worked well, but as customers from other industries increased, the problem arose that people took the product as not made for them. In a 2016 interview, he described the experiment of renaming the plans to Solo, Team, and Business. Trial signups dropped, but paid customers increased a little and the purchase price point rose.

Behind these decisions were interviews that traced the process by which customers actually bought. Gamez asked what customers had used previously, what event had pushed them to look for an alternative, and when they became sure that Bidsketch was right for them. He investigated the experience of customers who paid and customers who canceled to find problems in the pricing page, the feature descriptions, and the onboarding. It was an approach that valued the specific situation in which a purchase or a churn occurred over a survey that listed preferred features.

SignWell Emerged While Reworking Bidsketch

The second business took shape while he was cleaning up the technical burden of Bidsketch. Through years of operation and changes of development team, the code had grown old and it became hard to add the features he needed. While redesigning the product, Gamez noticed that existing customers wanted a tighter signing capability than integration with external e-signature services.

The first idea was to build the e-signature feature first and combine proposal writing on top of it. As development and customer support progressed, the nature of the requests and the customers making them moved further and further away from Bidsketch's existing market. Judging that e-signatures had independent demand on their own, Gamez adjusted the product direction. A rework plan for the existing product turned into a separate business serving a new customer base.

According to the company's about page, SignWell started in 2019. It used the name Docsketch at first and later changed to SignWell. The basic direction of the product was to provide an e-signature service that reduces complex settings, is easy to use, and carries a low price burden.

In addition to existing customer demand, he also researched users of competing products. He recruited users of competing services through Twitter ads and heard about their experience for 10 minutes in exchange for an Amazon gift card. He also attached a survey to the pre-launch page to identify complaints about price and usability.

The first version focused on the core task of uploading and signing a document. It had no API or several other advanced features, and the audit trail report that proves the signing process was initially created by hand whenever a request came in. As he observed actual customer use, he added the automation and features that were needed in sequence.

Connecting People Looking for Contract Templates to Signing Customers

The method that worked best for SignWell's early customer acquisition was free contract templates. Gamez noticed that people who downloaded a contract would need to get it signed in the next step, and he said the related material brought in more than 100,000 monthly visitors. In effect, he met potential customers one step before they searched directly for an e-signature product.

The revenue model is a structure that moves from free use to a paid subscription based on usage volume. Based on the public pricing as of September 2026, the free plan provides three documents per month, and the Light plan costs $12 per month when billed monthly or $10 per month when billed annually, for one sender. Paid plans provide an unlimited number of documents and are distinguished by the number of senders and team features.

The developer API opened another path to use. Other software can integrate SignWell to send documents and collect signatures inside its own service, and API pricing is charged according to the number of documents processed. With a lower per-document rate as monthly volume grows, it accommodated both the subscription product that people use directly and the demand for automated, high-volume processing.

As the product grew, security and organization management became important selling points as well. The company now offers an audit trail, a SOC 2 Type II audit report, and HIPAA compliance, and provides onboarding support and API implementation support for large teams. Its scope widened from a purpose of simply collecting a signature as an individual to a product that handles enterprises' adoption processes and operational requirements.

How He Maintained Both Products and the Shift to a Team Business

On funding, he made a different choice than with the first business. SignWell was included in TinySeed's spring 2020 investment portfolio, and Gamez said the additional resources and support network after the investment reduced his burden. So SignWell's growth includes not only customer revenue but also external investment and accelerator support.

Although he owned both products at the same time, he did not split the energy he put into growth equally. In a 2023 interview, Gamez said he maintained Bidsketch as a mature and stable product while concentrating his growth-related capacity on SignWell. Bidsketch still needed support for new customers and updates, but he reduced the operational burden by cutting back large-scale feature expansion.

SignWell in its growth phase should be classified as a team business. In an August 2025 interview, he covered the process of finding and hiring a CEO, the lessons from hiring a COO, and how to delegate important work. The founder's role also expanded from developing directly and responding to customers to building the executive team and making the organization work.

Gamez himself did not recommend building a second product as a general formula for growth. He believed that jumping into a new product to escape a stalled first business scatters focus and can create tasks harder than the existing problems. In his case, the conditions that made expansion possible were adjacent demand confirmed from existing customers, the operating foundation of a mature first product, and the choice to concentrate his capacity on the new product.