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:

In 2016, Slack CEO Steward Butterfield stated, “I think we can get away without having a sales team in any kind of traditional way probably forever.”

Same story for Palantir’s CEO, Alex Karp. He once said he’d only hire a sales team if investors forced him to. Or if he was “hit by a…

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.
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?


COVID-19 is reshaping the market like we’ve never seen before. As the pandemic wears on, leaders must determine which way the wind is blowing and set a course for solid ground. Everyone needs to find their own way.

Your customers, more than anything else, are your compass as you navigate these choppy waters.

The best companies are tweaking sales systems, adjusting their go-to-market strategy and rediscovering customers’ needs as they evolve.

Even if your business is thriving, you can’t do nothing — that’s like saying nothing’s changed. And your customers’ buyers might not be so lucky with a potential painful…

I got off the phone with a brilliant founder last night who has decided to “do enterprise sales” because she had experience working for a mega-brand and recognized a gap in the market as a result.

This process of arriving at or deciding to pursue enterprise sales is pretty common in the startup world.

However, I can say from first-hand experience that building the team you’re thinking of will be different than your expectations. And it will morph again when you have a few clients under your belt and continue to evolve as you get a foothold.

I’ve been fortunate…

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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