How to Hire the Right VP of Sales for Your Startup

Sales recruiting is broken. The sad truth is that VP of Sales are turning over within 19 months—and that timeline is shrinking.  

Not only that, the market has heated way back up and the VP of Sales is one of the most sought after roles. Yet, it’s one of the hardest to fill due to a supply vs. demand issue. 

What is the hardest executive hire you’ve made?

Image from First Round’s State of Startups Report

To add insult to injury, the odds are against the first VP of Sales hired in a startup, churning within 12 months. 

The consequences of getting this critical hire wrong are devastating:

One of the main reasons startups struggle getting this hire right is because of the language barrier between technical founders and sales. Technical founders tend to focus on outcomes, where sales leaders focus on the why and how to get there first. This isn’t linear and there are many shades of grey when it comes to sales.  

Therein lies the dilemma.

This isn’t an MVP scenario. This is a hire you want to get right the first time around. The VP of Sales will make or break your startup’s ability to propel you forward. Make the wrong choice, and you’ll be digging yourself out of a deep hole longer than you could imagine.

Here’s where to start.

Getting clear with your startup’s needs

“Hiring the right person at the right time with the right background is critical for success, and in a startup, an early head of sales is likely to be a hands-on contributor who also has the capability to manage a handful of people.” – Peter Levine

We recently worked with a startup that was coming off of their 2nd VP of Sales mis-hire in 3 years. When I probed to understand what their hiring process looked like, they shared that they had gone with a gut decision based on behavioral questions and a 30/60/90 presentation. 

Mayday!

Why?

Because it doesn’t tell you anything about the actual practice of what it would really be like to work together and was anchored in emotion and theory.

Before you initiate a recruiting process, get clear and specific about who and what you’re looking for in a VP of Sales that’s appropriate for your startup—not what everyone else thinks you should do.

• Know which superpower to optimize for: Sales leaders have no more than two “superpowers”, according to Doug Landis (I couldn’t agree more). They are company management, process management, culture management, and deal management. Assess your buyers, team, process, and roadmap to suss out which one you need most. Anchor yourself to where you are today and the near future, not what you aspire to be in 10 years.
• Pay attention to your stage: Not all stages of startups are created equal. Hiring too early–i.e. before you have validated the market or revenue, and you’re setting them up to fail. The VP of Sales role is NOT about launching your business. It’s about growth and scale.

Some questions to help you pinpoint timing:

• Do you understand your ICP, market, and buyer journey?
• How many customers do you have?
• Where is your revenue (you want to start thinking about the VP of Sales after $1MM in ARR)?
• What does your sales process look like?
• Do you know why your customers buy, why they stay, and why they leave?
• What does your Marketing strategy entail?
• Is the product ready (especially for enterprise customers that require customization or integrations)?
  

Hire too late, and you’re simply losing revenue with a lot of opportunity lost on the cutting room floor. 

As you grow, the more you’re involved in the day-to-day of the sales side of your startup, the more you won’t be able to think about your business. Important details will start to slip. 

If you’re trying to manage a sales function without a detailed plan and process in place for too long, it will turn into a sticky spider web filled with a plethora of issues to rectify later. Poor planning with a lack of intentionality when it comes to anything that touches your buyer journey is the silent killer for many startups. 

Pro tip:  Founders, when you hang onto the sales team for too long, it leads to:

• The overall strategy suffering, missing key opportunities to grow and thrive
• Big costs from an inefficient sales organization
• Losing priceless ground in this competitive market to companies with similar products and strong sales teams in place

Timing is everything as they say and this visual complements of Tomasz Tunguz does a great job of reinforcing this point:

Leverage your network

It’s always worth networking before you come knocking on my door. It’s priceless market insight and can help you save a big fee if you find the right person. Just make sure you use a hiring scorecard to avoid getting caught up in the shiny objects!

Ditch the 30/60/90 presentation

I can’t tell you how many times I see someone request a template from the communities I’m involved in. It’s easy to slay a presentation, but what about the real work that comes with the job and how do you know? The short answer is with this approach, you don’t. 

Part of our secret sauce at ATP is creating a collaborative working session where you harness your inner Real World persona to stop being polite (please don’t ditch the manners) and start getting real to break down real business problems or parts of the role together.  Then you’re able to see how they think, prepare, connect, challenge, and respond to issues they don’t have the answer to. 

The closer you bring each candidate into the important bits and pieces of the role and business itself, the better your chances of making an A+ hire. 

Sayonara theory. Hello practical nuts and bolts.

What to ask in VP of Sales interview

No more generic cookie-cutter questions. For a VP of Sales role, you need to dig deep and get down to the brass tacks of what they bring to the table to understand:

• Why they did what they did
• Where they did it
• Who they did the work with and their true part of the story
• How they did it
• How they improved
• Lessons learned
• Outcomes

Here’s a list of questions you can use in your interviews:

• What do you think we need right now and why?
  • A VP of Sales will be able to share ideas from their toolkit (the best leaders have a tool box just like master builders and know which one to use at the right time with the right situation and how) – look for this vs. a one-size-fits-all playbook approach.
    
  • Pay close attention to if they really heard you and are thinking about how they can help vs. the read rinse repeat playbook that talks at you, rips everything up, and makes the wrong assumptions that can hurt your startup
• What’s important to you in your next role and why?
• What does FUD (fear, uncertainty, and doubt) look like in your startup and how have you dealt with it on your team and your buyers?
• What is your superpower?
• What are the top 3 things you’ve learned through our interview process and how does that translate into how you can help?
• What does sales process mean to you?
  • An excellent question my Thursday Night Sales partner in crime Scott Leese likes to ask is: what is your approach to hiring, onboarding, and retention?
• What are some of the signals you look for to know it’s time to add people to the team?
• What is the worst hire you’ve made?
  • How did you deal with it?
  • What did you learn?
• What’s your definition of a great hire?
• What technology do you need coming into the role (and why)?
• What goes into your forecast creation process?
• How do you track the progress deals within different segments and what metrics matter the most for each?
• How do you make sure silos aren’t created between Sales AND Marketing, CS, Product, Operations, etc.?
  • What specifically do you do beyond meeting regularly to work together to build the business?
• What is the largest growth you’ve personally led from A to Z – what threw you for a loop along the way?
• Why have salespeople failed on your team and how did you respond?
• What’s the hardest part of working with a Founder?

The more clear you are with your questions and they are with their responses, the better decisions you can make.

As you’re listening, ask yourself, “so what?”  If the dots aren’t connecting in a way that creates a meaningful answer to that question, it’s time to move on.

Pro tip:  I highly recommend using a hiring scorecard to keep yourself on track, consistent, and rooted in what matters most. The stories we start to tell ourselves aren’t always rooted in reality.

Don’t jump the gun 

Gone through a round of interviews, the chemistry is on 10, feeling the pressure to hire NOW, and think you’ve found the perfect candidate?  Tempted to call it a day and send the offer to get it done and over with?

Pump the brakes.  While diving right into the offer feels like a good idea, it’s better to be intentional to save yourself a heck of a lot of angst later. There are more effective ways to close a great candidate. 

For starters, do you know how this person is feeling about you and how they make career decisions? It’s important to take a breath, realize it’s a two-way street, and lean into a thoughtful, intentional, efficient hiring process.

Wrapping Up

Without customers, you have no business.And your VP of Sales is the catalyst for more customers.

The table stakes are high, and with 48+ different kinds of sales leaders to choose from, you don’t want to take this mission critical hire lightly.

It’s one thing to hire someone, it’s another to keep the person you worked so hard to hire in the first place. Design a process that truly uncovers what the candidates you’re considering are good at and how that maps back to the work you need to accomplish for your startup.  Then give them a real seat at the table where you can collaborate, challenge, and build the business together. You want a partner in crime that will think about the business broadly, not just from a sales viewpoint.  

Assess what your startup needs, stick to a people-centric, process-driven approach, and you’ll avoid making a costly mis-hire that sets your startup back.  

Need help? I’ve got you covered! My hotline is always on with an ear to listen and a mind to brainstorm.