Hiring your first head of sales is a really big deal for a growing SaaS startup. Most founders don’t get it right the first time.
Founders created the first revenue with super-savvy selling, then a sales hire or two who could keep up.
It’s a treacherous transition to hire a sales leader and build a sales team that can sell just as well as the founder.
If you don’t make this transition, you’ll stop growing and get stuck.
Phil Stern is an operating principal at Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies starting at around $5M ARR.
Mainsail offers deep operating support to the founders and 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.
The transition from a scrappy startup to a scalable revenue machine requires a very specific sales leader, especially in vertical SaaS.
Phil explains the specific traits required to succeed with your first sales leader on my podcast this week:
“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.”
Hire a scrappy player-coach as your first head of sales. Be clear with them to be very tactical most of the time and not be an armchair strategist.
In this episode, Phil shares his five keys to hiring the first head of sales in vertical SaaS to graduate from founder-led sales to a scalable sales team.
And how Mainsail experts partner with founders and their leaders to help them solve their most important GTM problems quickly.
Check out this thoughtful interview with Phil Stern on the Practical Founders Podcast.
What were your biggest mistakes and learning with your first sales hires and leaders?
How many first salespeople did you hire? 🙂
