Practical Founders Podcast
#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern
May 16, 2025
Phil Stern, Operating Principal at Mainsail Partners, specializes in growth equity for bootstrapped vertical SaaS companies. He shares insights on hiring the first head of sales to transition from founder-led to scalable sales. Phil highlights the importance of operational support and establishing trusting relationships with founders. He discusses the need for effective customer profiling and the transformative role of AI in SaaS. The conversation emphasizes how targeted investments can accelerate growth while ensuring product-market fit and a focus on key performance indicators.
58:20
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Quick takeaways
- Mainsail Partners emphasizes hiring a strategic sales leader as a critical first step to transition from founder-led sales to scalable sales teams.
- The operational support provided by Mainsail includes embedding specialists in key functions to tackle specific go-to-market challenges faced by portfolio companies.
Deep dives
Role of Mainsail Partners in Growth Equity
Mainsail Partners is a growth equity investor specializing in B2B SaaS companies, primarily focusing on vertical software industries. They invest in bootstrap founders whose businesses have reached around three to five million in annual recurring revenue (ARR) and demonstrate clear product market fit. Mainsail not only provides capital but also offers extensive operational support through a dedicated operations team with specialists across various functions. This partnership approach aims to facilitate the scaling of businesses while ensuring that the founders maintain significant equity and control over their ventures.
