#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern

13 snips

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.

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INSIGHT

Bootstrapper Mentality for Sales Leader

The first head of sales must embrace a hands-on bootstrapper mentality.
They must sell alongside managing, coaching, enabling, and strategizing without being an armchair exec.

ADVICE

Hire Sales Leader with Talent Partner

Partner with your growth equity to define the sales leader profile and customize the hiring scorecard.
Use internal talent teams to find and place the right sales leader quickly and cost-effectively.

ADVICE

Refine ICP and Pricing Strategy

Perfect your ideal customer profile and build go-to-market aligned with it.
Manage pricing continually and adjust as product and market evolve, reflecting true value.

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Phil 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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