Software Sales Tips by Matt Wolach

Scale Your SaaS

How to Win Large Enterprise Deals as a Startup – with Ron Gidron


Embarking on the entrepreneurial journey in the tech industry can be like a roller coaster ride – it’s exciting, filled with energy, and demands unyielding dedication. 

In this episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach had a candid conversation with Ron Gidron, Founder and CEO at xtype. Read on to delve into the whirlwind of experiences, insights, and lessons learned while scaling a tech startup, particularly in targeting the enterprise sector.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 294, “How to Win Large Enterprise Deals as a Startup – with Ron Gidron”

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

Guest: Ron Gidron, Founder and CEO at xtype


Ride the Wave of Growth

Ron’s story at xtype commenced with an unconventional genesis. Instead of ideating a product, they stumbled upon a critical problem within the ServiceNow ecosystem, sparking their journey. This revelation led them into uncharted territory, diverging from their comfort zones in enterprise software into a domain they hadn’t explored before. This taught startup founders how to ride the wave of growth as businesses could progress slowly at the beginning, but in a fast-paced industry, growth washes like a huge wave and could happen when you least expect it.

Shift the Paradigm in Enterprise Sales

Ron took an unconventional route in targeting enterprise deals, diverging from the typical bottom-up approach in DevOps spaces. They identified the core personas—platform owners and architects. This becomes crucial for their solution, reframing their strategy to address enterprise needs directly, and so Ron advised founders not to be afraid to shift the paradigm when the time calls for it.

Understand Enterprise Dynamics

Ron emphasizes the time-intensive nature of enterprise software sales cycles, often spanning months for substantial deals. Selling to enterprises means selling to a team, not just an individual. Hence, understanding the organization’s structure, aligning with various stakeholders, and establishing compelling events are paramount in expediting sales cycles.

Employ Tenacity and a Problem-Centric Approach

The essence of Ron’s advice to aspiring tech leaders echoes the importance of tenacity. Fall in love with the problem before the solution, assess its significance, and embrace the relentless pursuit of its resolution. Putting oneself in a corner, driven by an unwavering passion to solve a genuine problem, fuels the journey.


The Foundation of Success

The initial phase of any software business doesn’t come without challenges. However, Ron highlights two pivotal decisions that set the tone for their success. 

Firstly, acknowledging their ignorance and starting from scratch within the ServiceNow ecosystem was essential. Secondly, they only raised funds once they had a profound understanding of the problem and evidence of traction. This old-school approach mirrored the garage-style work ethic, focusing on learning, building, and venturing into business.

The Grit Behind Early Wins

Even with a small team and limited resources, early deals can be secured through sheer persistence. Cold calls, emails, and LinkedIn outreach formed the backbone of their sales efforts. Their unwavering focus on solving a pressing problem resonated even with larger enterprises despite their modest beginnings.


Ron Gidron

[5:11] “Fall in love with the problem versus a solution.”

[14:43] “Selling to enterprises means selling to a team, not just an individual.”

Matt Wolach

[18:59] “It’s not always the best product that wins; it’s how you make the buyer understand their problem.”

[21:22] “If the problem is big enough, they won’t care how big you are or how long you’ve been around.”


To learn more about xtype, visit: 

You can also find Ron Gidron on LinkedIn: 

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