Software Sales Tips by Matt Wolach

Scale Your SaaS

Ways to Overcome the Ups and Downs of the Software World – with Will Robinson


In the fast-paced world of software sales, adaptability is the name of the game. 

In this week’s episode of Scale Your SaaS with host and B2B SaaS sales coach Matt Wolach, we’re delving into today’s insights from a seasoned industry leader, Encapture’s CEO, Will Robinson. He offers a glimpse into the dynamic world of selling software to banks and lenders. 

From adapting to changing market conditions to transforming the company’s focus, this discussion unveils the challenges and successes of a thriving software business. Let’s explore the key takeaways and the journey of Encapture, a company at the forefront of innovation in the SaaS industry.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 288, “Ways to Overcome the Ups and Downs of the Software World – with Will Robinson”

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

Guest: Will Robinson, CEO at Encapture


Adapt To Market Changes

The software industry is no stranger to fluctuations in market conditions. As this episode highlights, selling software to banks and lenders has seen significant shifts. These changes include fluctuations in interest rates, shifts in customer behavior, and even the flight of deposits from traditional banks to emerging players in the financial industry.

For software companies, it’s crucial to stay agile and address the evolving needs of their clients. This means continuously revising the sales message, understanding where prospects allocate their budgets, and identifying the pressing problems they aim to solve. As a result, software companies must evolve their products and services to remain competitive and support their clients effectively.

Learn To Shift Focus

One of the notable aspects of the discussion is the Encapture’s ability to pivot its focus over time. Encapture started as a professional services provider, helping implement third-party software in various industries, including banking.

However, the company recognized the potential in document collection and processing and developed its software to address the inefficiencies in this area. This strategic shift toward creating its product marked a transformative period in the company’s history.

The transition from professional services to software as a service required a change in strategy and a clear vision for the company’s future. This change was challenging, but it ultimately allowed Encapture to thrive in a highly competitive market.

Be Open To Embrace Change

Will also address the challenges of introducing change into an organization. As Encapture’s CEO, he admits that only some on the existing team were ready to embrace the new strategy. This experience is a stark reminder that change can be met with resistance, especially in long-established companies.

However, sometimes, the best course of action is to let go of team members who are not aligned with the company’s evolving vision.

In some cases, it may be more efficient to bring in fresh talent that shares the company’s values and culture. This approach can create a more harmonious and focused work environment.

Innovate with Caution

Experimenting with new ideas and approaches is vital for business growth. However, Will’s experience also serves as a reminder that innovation should be aligned with the company’s core mission. Experimenting with clients outside the core focus can save time and resources. It’s essential to stay true to your core strengths and customer base while exploring innovative opportunities.


Take the Lessons From Past Mistakes as Catalyst for Change

Will openly acknowledges that not every decision was a winner and regrets holding onto employees who didn’t fit the company’s new direction. This willingness to learn from failures is a valuable lesson for all business leaders.

Will’s story offers valuable insights into the ever-evolving world of selling software to banks and lenders. Encapture’s journey showcases the importance of adaptability, segmentation, and focused growth. The ability to pivot, bring in fresh talent, and learn from past mistakes sets successful companies apart in this competitive industry.

Whether you’re an industry veteran or a budding software entrepreneur, these lessons can be a compass for navigating the complex terrain of software sales, fostering resilience, and ensuring sustainable growth. 

Ultimately, it’s not just about selling software; it’s about embracing change and finding innovative solutions to real-world problems.


Will Robinson

[5:11] “It’s hard to get a legacy group of folks to change their mindset.”

[14:43] “Having a growth mindset is essential, and it’s easier to backfill and replicate knowledge than I thought.”

Matt Wolach

[18:59] “Process is huge.”

[19:03] “I love that you narrowed your niche, and you said we’ve got to focus on these particular prospects and customers because it just makes everything within the business run so much easier. It makes your marketing more focused and tight and makes the buyers realize that you are perfect for them specifically, which is amazing.”


To learn more about Encapture, visit: 

You can also find Will Robinson on LinkedIn: 

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