What it takes to be a successful VP of Sales in Tech

So you’re considering hiring a VP of Sales for your startup. Are you sure you know what to look for?

After working with more startups than I can count over the years, I can tell you this much: most Founders they know what makes an outstanding VP of Sales. But they don’t realize how much they know about hiring for this crucial position.

Of course you’re looking for a smart VP of Sales with tons of experience under their belt. What you may not be looking for are all the other nuanced characteristics and traits that make someone…


There’s a right and wrong time to hire a VP of Sales.

According to First Round’s 2019 State of Startups report, sales leadership is the most difficult hire to make.


Enterprise Sales is a Completely Different Beast!

Closing a blockbuster multi-million dollar deal with a Fortune 100 company can be a massive win for a startup.

But don’t get too attached to the idea without knowing what you’re getting into.

Enterprise sales is not a simple switch to make from SMB sales — it’s a completely different beast.


Perception isn’t reality for sales hiring in startups.

In today’s market, understanding what salespeople want in their next career move is imperative.

Truth be told, I find that most companies don’t, even though they’d argue otherwise.

For example, while working in the HRTech space (which is a small world where those of us in enterprise sales knew each other) a well-known brand approached me about joining the team after they asked a client who their favorite salespeople were.

I entertained a few conversations, but never considered it further because each time, they’d talk to me about all of the things they thought were important (their amenities of working…


Without sales you can’t grow a startup

Pushy, sleazy, manipulative… these are all words I’ve heard when talking to tech founders about sales. Many of them believe that if you build a great product, then the sales will just come naturally.

Here are a couple of quotes that showcase this mentality in action:


When times get tough, companies that show up for their customers quickly become the new favorites.

When times get tough, companies that show up for their customers quickly become the new favorites.

We’ve all heard of businesses showing their true stripes for better — and for worse.


Sales hiring isn’t one-size-fits-all, especially in enterprise sales.

When I first wrote this for OpenView, we were in a place where unemployment was at an all-time low and hiring was top of mind.

My, oh my, how times have changed in such a short amount of time.

Whether your company has paused hiring, is still hiring or will be in the future, having the right people for your business and stage will always be a priority.

Building an effective (and committed) enterprise sales team for the long haul starts with the people you hire. …


Back in the dark ages (when dinosaurs roamed the Earth), I grew up in the enterprise sales world of having to do everything myself:

  • Researching my market
  • Prospecting my target buyers
  • Discovery calls
  • Strategy
  • Sales meetings
  • Closing
  • Account management
  • Client success

And while I understand why so many celebrate the ways found to make the sales process more ‘efficient’ through segmentation, we’ve gone too far.

Think I’m wrong? Start talking to your buyers.

Case in point complements of Will Allred via LinkedIn:


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……

Amy Volas

I help startups hire sales leaders without the cringe • Founder/CEO • 2X Entrepreneur • Personally closed $100MM+ in revenue (and counting) • LinkedIn Top Sales

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