Phil Stern was an experienced software sales leader at several companies before joining Mainsail to focus on helping our portfolio companies scale up. A member of our Growth Team, he helps founders solve challenging problems with sales leadership, org design, inbound/outbound strategy, processes and data, AI automation, and more.
He joined Greg Head for an episode of Practical Founders to discuss:
- Five keys to hiring your first head of sales to graduate from founder-led sales to a scalable sales team
- How Mainsail partners 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 sales processes opportunities for growth
- Why Mainsail is focused on vertical software companies with founders who are often deeply experienced in their domains
Listen or Watch the Episode on PracticalFounders.com
Listen on Spotify
Listen on Apple Podcasts
Watch on YouTube
Quote from Phil Stern, Partner 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.”
