Software Sales Tips by Matt Wolach

Scale Your SaaS

Understanding the Power of AI – with Jon Ricketts


In the rapidly evolving landscape of technology, the power of AI is undeniable. One company that has harnessed the potential of generative AI is Writerly. I sat down with the Co-Founder and CEO, Jon Ricketts, to delve into the inspiration behind the platform, its journey, and its invaluable role in content creation. 

Join us as we explore how Writerly is shaping the future of AI-powered content generation and the wisdom Jon imparts to fellow software founders with host and B2B SaaS Sales Coach Matt Wolach. 


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 277, “Understanding the Power of AI – with Jon Ricketts”

Host: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor

Guest: Jon Ricketts, Co-Founder & CEO at Writerly


Navigate High Growth: Key Ingredients for Success

The conversation takes a turn toward Writerly’s remarkable growth trajectory, with projections of over one million users within its first year. Jon attributes this success to a multifaceted approach. He commends his outstanding team, emphasizing the value of hiring capable, adaptable individuals hungry to learn and contribute. 

Jon also acknowledges the tailwind generated by the concurrent launch of Writerly and open AI’s ChatGPT, which amplified interest in the field of generative AI. Despite the fatigue surrounding AI in the market, Jon notes that Writerly’s growth is a testament to its meaningful impact and the growing enthusiasm for AI-driven solutions.

Create a Lasting Impact: Educating the Market and Fostering Understanding

Jon emphasizes the need for market development and educating potential users about the possibilities of AI. He reveals Writerly’s strategy of addressing enterprises’ specific challenges, stressing practical applications rather than a one-size-fits-all approach. 

By collaborating with advisors from large organizations, Writerly aims to facilitate widespread adoption by addressing real-world needs and overcoming barriers to implementation.

Craft a Winning Team: Nurturing Talent in a Startup Environment

Building a successful team in a high-growth software startup requires careful consideration. Jon shares his insights into creating a dynamic team by initially seeking adaptable generalists who can wear multiple hats and later transition into specialists. 

He emphasizes the importance of a shared vision and enthusiasm among team members. Jon notes that contrary to expectations, post-COVID, many team members prefer working in a physical office environment, fostering collaboration and camaraderie.

Part Words of Wisdom: Embrace the Journey and Dive In

Jon offers sage advice to software founders entering the startup arena. He advocates for a wholehearted commitment, urging founders to embrace the journey with a “burn the ships” mentality. 

Jon encourages founders to fully invest their passion and creativity into their endeavors, acknowledging that while the path may be challenging, the rewards are well worth the effort. He underscores the importance of cultivating enthusiasm, building a robust team, and navigating challenges with a sense of purpose.



The Spark of Innovation

Jon begins by recounting the journey that led to the platform’s inception. He reveals that his fascination with generative AI was sparked by the curiosity that naturally arises upon encountering this transformative technology. He recalls realizing that AI could enhance daily tasks and revolutionize various aspects of enterprises and large organizations. 

However, he acknowledges the hesitancy that accompanies the promise of AI and the need to understand its risks before integration. Over the years, Jon’s perspective evolved alongside the general public’s, transitioning from skepticism to embracing the potential benefits of AI.

Enhancing Content Creation Through AI

Jon sheds light on AI’s core strengths, particularly its role in content creation. He emphasizes the platform’s ability to serve as an inspirational tool, providing creative sparks and novel ideas. 

While Writerly can generate new content, its true expertise lies in innovatively transforming and presenting existing content. This feature proves indispensable for businesses with a digital presence, helping them overcome writer’s block and craft impactful messages. 

Jon also discusses the emerging trend of AI-driven automation and how Writerly is positioned to help enterprises streamline their operations, bridging disparate data systems to create valuable content.

AI’s Role in Content Authenticity: Balancing Human and AI Contributions

A common concern arises about the authenticity of content generated by AI. Jon addresses this concern by highlighting the importance of incorporating a human touch. 

While generative AI can expedite tasks, ensuring content credibility and search engine optimization requires human editorial input. Jon shares that content should collaborate with AI and human creativity, offering unique perspectives and ideas that truly resonate with audiences.


Jon Ricketts

[13:16] “AI is not going to go anywhere, and they are not trying to force it on large organizations.”

[23:13] “Embrace the burn the ships mindset. Nothing is guaranteed, but the chance of success is far greater when they put their head down and apply that mentality.”

Matt Wolach

[18:24] “Building a successful team in a high growth startup is difficult, but also very important.”

[25:19] “I teach my clients we don’t want to dip our toe in the water. We need a full cannonball. Get in there.”


To learn more about Writerly, visit:

You can also find Jon Ricketts on LinkedIn at:

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