The Right Time to Hire a VP of Sales for Your Startup

Amy Volas
8 min readNov 29, 2020


I’m a co-founder/host of a community called Thursday Night Sales and this topic came up in a chat I had with one of our members.

They told me their company (SMB focused) has a growing sales team that is currently led by the CEO. They’d tried hiring a Head of Sales, but it turned out to be a bad hire and they had to let that person go.

They specifically asked: what metrics or discussion points can be presented to the CEO to help shift his thinking and build trust to hire for the VP of Sales position again?

Well… it’s complicated.

Before you reach that coveted ‘unicorn’ status, there’s a lot of work to be done to drive revenue and growth.

One of the most important takeaways I could ever share that different stages of business require different sales leaders. As much as we want it to be easy with a one-size-fits-all solution, that’s simply not the case.

There are 48 different types of VP of Sales, so make sure you choose wisely!

Furthermore, the VP of Sales is one of the most important and influential hires a startup will make. And it also has the potential to be one of the most disastrous if you botch it up (think 7-figure lasting effects).

“70% of Saas First VP Sales don’t make it to 12 Months. It’s one of the most common, and also most devastating mishires in startups.” — Jason Lemkin

So why is a bad sales leadership hire so devastating? Because that person will touch nearly every aspect of your business and is ultimately responsible for your buyer journey and their experience, which directly affects your bottom line. Without sales you have no business.

So, let’s not get there in the first place. As long as you hire your VP of Sales at the right time to do the right work, with the right people, and the right process (a la an intentional, defined process to make an



Amy Volas

Helping SaaS startups hire executive Sales and CS leaders without the cringe ⋆ Personally closed $100MM+ ⋆ Founder/CEO ⋆ 2 Exits ⋆ LP ⋆ Sharing lessons here