A Guide to Hiring a VP of Sales

If you’re an early-stage founder and you’re on the fence about hiring a VP of Sales for your startup, this post is for you.

First, a little bit about me. I was an early or first sales hire at a number of fast-scaling fintech startups— Plaid, Berbix (acquired by Socure), and Meld.io. I’ve seen what it looks like when you build a team and get it right, and I’ve seen what it looks like when you get it wrong.

Hiring a VP of sales is a balancing act. If you’re too early, your VP of Sales will do exactly what they were hired to do: build a team. They’ll go on a hiring spree to justify their hiring, and the team will be underwater chasing after unrealistic goals. If you’re late, your VP of Sales will be herding cats trying to manage a cacophony of bad data and broken processes.

Either way the outcome is the same: crash and burn.

So my first recommendation is…

Take a Hard Look in the Mirror

Are you early, still trying to achieve your first significant revenue milestone(s)? 

I won’t sugar-coat it. This is not a scenario a VP of Sales can excel in. You haven’t proven out product-market-fit. Your VP of Sales will struggle to build and scale an effective operating strategy because they’ll face product-related challenges beyond the scope of their role and expertise.

Here’s another important question we should get out of the way: Have you– as a founder– successfully sold the product yet? 

This firsthand experience is invaluable. 

You can’t understand what it means to build a sales process— or understand the unique challenges your product solves— without first having been on the front-lines yourself. 

The ability of any sales rep (let alone a VP of Sales) to match or surpass your success is a telling indicator of your product's market readiness.

Recognize that— and recognize that top-tier sales talent will be hesitant to join you if you haven’t proven the product's market worth yet.  

Work Backwards to Set the Stage

I like going through the mental exercise of ‘working backwards.’ It cuts through the noise and allows for a focus on the end state and the ideal path to get there.

So what’s the ideal scenario for an incoming VP of Sales? 

I’d argue the landscape looks something like this. You have:

• 2-4 SDRs/BDRs prospecting full-time.

• 2-4 AEs closing prospects sourced by your SDR/BDRs.

• $1-2M+ in ARR.

If this looks like you, right now you’re probably thinking “LFG! Get me a VP of Sales stat!" 

Not so fast.

How many of your SDRs are hitting targets consistently? More importantly, how many of your reps are hitting or exceeding quota? 

Even if performance is inconsistent across your sales org— you might think a sales leader can right the ship. And maybe they can. But what’s more likely is you— once again— haven’t hit product-market-fit. 

And that’s a challenge a head of sales is ill-equipped to tackle.  You want your head of sales scaling a team, building an operating plan for hitting or exceeding revenue targets. You don’t want them solving product-fit problems.

So if your sales team isn’t seeing some level of ‘hockey-stick-type’ growth, hold off on hiring a head of sales from the outside. 

You’re not there yet.

Before we proceed, I want to acknowledge there's an entire chapter in this journey about hiring your first AEs—a crucial step that deserves its own dedicated discussion. Stay tuned for an upcoming post on how to build a team of killer AEs.

Prioritize Internal Hiring When Possible

Homegrown talent is the best kind of talent, so don't overlook the goldmine within your own ranks. 

Your team members, especially those who you’ve personally coached, are primed to take the lead. They’re already deeply familiar with the product, processes, and most importantly, your customers. They understand them inside-out. This knowledge allows them to identify your ICPs, and to effectively coach a new team from day one.

Your internal candidates are also well-versed in your current processes and can pinpoint areas for improvement. This ‘insider’ perspective is invaluable, and not something you can easily find outside.

If your ideal team member is green in certain areas, like team leadership, don't sweat it. A coach can bridge these gaps at a fraction of the cost of hiring an experienced VP of Sales. Plus, they can continue to contribute as ICs while transitioning into a player-coach role, gradually evolving into the full VP of Sales position. 

This step-wise approach will not only save you money, it also maintains continuity vis-à-vis customers, and leverages the company and product knowledge they’ve earned to the fullest.

Only When Internal Hiring Isn't Feasible, Look for Experienced Candidates

If you determine nobody in your pool of internal candidates is up to the task, I'll once again ask you to take stock of where you are: 

What is your current revenue number, and where do you want to be? 

If your startup's at $1 million in ARR with ambitions of getting to $10 million, your best bet is someone who’s already navigated this exact journey. 

No silver bullet here. Find someone who's done it before and hire them. Aside from things like culture-fit, they’ll be checking a ton of boxes. 

But here's the kicker: the real challenge won’t be in finding them, it’ll be in convincing them to join your team.

Take Johnny Sales here as an example.

He’s pumped. He recently led his sales org from $1m to $10m in ARR and he’s not stopping there— why would he? 

His company wants to keep growing, and so does he. 

So Johnny’s revenue target that was once $10m is now $50m— and guess what? He’s categorically convinced he's the guy for the job, and you can’t blame him.

The problem is, scaling from $10 million to $50 million in ARR isn't the same as going from $1 million to $10 million. It demands a different skill set, a different temperament. It's about scaling operations, managing larger teams, and navigating more complex dynamics. 

The person you’re looking for is not the person who can catapult you to $50m, or even $100 million. But they’re the mastermind to bridge you to $10 million. They've got the playbook and they can execute it— having been there and done that. Your quest is to find this rare gem and, more importantly, to make them see why rewriting a success story with your company is the next chapter they want to write.

So you’re looking for someone who understands all that, someone with a massive amount of emotional intelligence who knows precisely where their strengths lie.

Our Johnny Sales is not that guy.

Wrapping up, hiring a VP of Sales starts with a clear-eyed assessment of where your startup stands, particularly in terms of revenue. My advice leans towards promoting internally whenever possible, capitalizing on existing talent who understand your business inside-out. If that's not an option, seek a specialist — someone who's navigated the exact growth path you're on and who scores high in EQ.

Every startup has its unique challenges, and there's no one-size-fits-all. If this post resonated with you and you're contemplating whether you're ready for a head of sales, let's connect.