#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern
Release Date: 05/16/2025
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#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern
Practical Founders Podcast
Phil Stern is the operating principal of , a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams. Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops...
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info_outlinePhil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams.
Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company.
In this episode, Phil discusses these important topics.
- The five keys to hiring your first head of sales to graduate from founder-led sales to a scalable sales team
- How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly
- How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth
- Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains
Quote from Phil Stern, Operating Principal at Mainsail Partners
“Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes.
“You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you.
“If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them.
“It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.”
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