Software Sales Tips by Matt Wolach

Scale Your SaaS

How To Mitigate Business Mistakes – with James Weir


Starting a software business can be intimidating, especially for those who have not envisioned themselves as entrepreneurs. However, sometimes, the most successful ventures emerge from unlikely beginnings. 

This week’s episode of Scale Your SaaS delves into the journey of ndaOK with CEO and founder James Weir. This company began with a reluctant founder but has experienced remarkable growth by addressing a common problem with innovative solutions. Sit back as we discuss mitigating mistakes through intelligent decision-making with host and B2B SaaS Sales Coach Matt Wolach.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 285, “How to Mitigate Mistakes Through Smart Decision Making – with James Weir”

Host: Matt Wolach, a B2B SaaS Sales Coach, Entrepreneur, and Investor

Guest: James Weir, Founder and CEO at ndaOK


Connect with an AI Expert

Seeking validation for their idea, the founder reached out to an AI advisor named Russell Full Smith, a leading expert in the field. Rather than dismissing the idea, Russell confirmed its feasibility and expressed enthusiasm for its potential. This pivotal moment marked the beginning of ndaOK’s journey.

Research and Validation

Before building a product, ndaOK spent about a year researching and validating the concept. They wanted to ensure that the problem they aimed to solve was not unique to the founder but a widespread issue faced by many software companies. This process involved speaking with potential customers, conducting surveys, and gathering feedback.

Find a Common Pain Point

The research phase confirmed that NDAs posed a significant problem for numerous companies, regardless of their industry. Even businesses in the business-to-consumer (B2C) sector eventually encountered NDAs in their dealings. With this knowledge and potential customer support, ndaOK embarked on developing its product.

Launch to Early Success

In early 2021, ndaOK officially launched its product. They found early success by focusing on the pain points of a specific niche – private equity firms and investment banks. These organizations dealt with a high volume of NDAs, making ndaOK’s solution incredibly valuable to them. This initial success allowed ndaOK to refine its product and customer base.

Niche Down, Then Expand

ndaOK’s journey highlights the importance of starting with a specific niche before expanding to a broader market. By targeting a segment with acute pain points, they could fine-tune their product and gather valuable insights. Once established, they began extending their services to other industries and organizations.


The Reluctant Founder

The story of ndaOK begins with a founder who has yet to plan to launch a company. After practicing law for over a decade in New York, the founders moved to Austin, Texas, with no intention of continuing their legal career. However, life had other plans. The founder took on various roles, eventually becoming the CEO of a tech company using artificial intelligence (AI) to categorize household hazardous waste more efficiently.

From Law to Tech

The first step in the founder’s entrepreneurial journey was shifting from a legal career to the tech industry. However, their role as CFO at a software company sparked the idea for ndaOK. In this position, the founder dealt with numerous nondisclosure agreements (NDAs) every week, which left them frustrated with the tedious and repetitive nature of the process.

The Birth of an Idea

The idea for ndaOK emerged when the founder realized that NDAs, while essential, could be streamlined and automated to simplify the review and redlining process. The founder’s firsthand experience dealing with these agreements for two and a half years led them to question if there was a better way to handle NDAs. This concept became the seed from which ndaOK would grow.


James Weir

[17:41] “We started to develop that FOCUS. And now, as we’ve nailed that market and that customer segment, we’re starting to spread out and go wider again and start to deal with enterprise sales teams and real estate investors and others that have that problem at a large enough scale where the solution is important for them.”

Matt Wolach

[12:53] “Email effectiveness is dwindling down and down every year.”


To learn more about ndaOK, visit: 

You can also find James Weir on LinkedIn: 

For more about how host Matt Wolach helps software companies achieve maximum growth, visit