Before New Sales Hire

Founders: 7 Critical Questions to Ask Yourself BEFORE Your First Sales Sales Hire


Hiring salespeople is an exciting time… it often means you’re ready to (or in the process of) growing your startup!


However, it can also be quite a daunting task — one that I see trip up many startups and result in painful mis-hires and blown opportunities.


One of the main reasons I see this happen: 


Startups often think (consciously or subconsciously) that scaling or building a sales team is as simple as “getting bodies in the door yesterday.”


Nothing could be further from the truth! 


The reality is not all salespeople are created equal (and neither are startups). Just because someone has amazing sales numbers and posts about it on LinkedIn with a big following doesn’t necessarily mean they’re a good hire.  What they had to do to achieve those numbers may be totally different than what they’ll have to do to be successful with you!


So how do you know which salesperson is the right hire for your business? 


The answer starts with YOU.  The key is to do an intentional deep dive into your business and evaluate your needs before you begin recruiting.


Here are 7 questions to ask yourself about your business that will help you differentiate between a candidate who will serve your business best and one that won’t.


1. What Is Your Mission?


This might seem like a strange place to start, but just about every sales candidate we speak to cares deeply about selling something they believe in.


And as Simon Sinek so astutely points out, “People buy from those who believe what they believe.”


So if your reps don’t believe in what they’re selling, how will your buyers?


“The first sale happens in the heart of the salesperson.”


That’s why one of the most important things you can do is to make sure you’ve firmly established your vision and mission — and can articulate it in a compelling way during interviews (including examples of how to back it up).


This will act as a magnet. It will draw the salespeople who love what you do to join the mission and will repel those who don’t.


And this is critical because when you hire people who want to be there, it will boost engagement right off the bat — something a study by Gallup showed to result in a 22% boost in productivity.


2. Which Market Are You Targeting With This Role?


There is a big difference between selling to the SMB, Mid, and Enterprise markets. And knowing how to differentiate experience in each (as well as which you’re selling to) is absolutely critical.


Hiring an Enterprise Account Executive is very pricey — and overkill for a business that’s selling to the SMB market. 


It’s like using a sledgehammer when you only needed a rubber mallet. 


The same applies to the Enterprise market. Hiring an SMB rep (even a good one) will likely have them way out of their element and not create the results you’re after. 


The mindsets and skillsets are simply different. 


Just like the differences between inbound, outbound, and full-cycle sales.


What’s the difference between Enterprise, SMB, and Mid-Market? 


Most of the ways people differentiate and define these markets involve deal sizes, sales cycles, etc. But the truth is, these things don’t really tell you what you need to know to be successful.


These are the definitions that will:


“Enterprise sales is all about fitting a custom solution for a single large buyer, where SMB is about finding lots of smaller buyers who are a good fit for your existing product. 


Mid-Market is somewhere between the two. Deals in this segment sometimes require customization and are largely differentiated from the other two on deal size and complexity.”


Understanding these differences is key. It affects the way the person you’ll hire will need to sell to be successful.


Will they need to focus on optimizing for a volume-driven approach, which is needed to be successful in the SMB world? Or will they need to prioritize deep discovery to find the perfect solution that enterprise buyers require to make a purchase? Or do they need a mix of both on deal sizes that are somewhere in the middle?


The skills associated with each approach are different. So be clear on which market you’re going after, and the approach your hire(s) will need to take to be successful!


3. How Much Selling (If Any) Has Been Done So Far? What Have You Learned?


This will depend on whether you’re starting from square one (i.e., this is your first sales hire) or not. If you’ve got a team and want to expand, you can skip to question #4.


If it’s your first sales hire (or you’re still trying to get your first hire right)… 


If I’m honest, most startups hire salespeople too soon. 


In fact, I regularly advise early-stage founders to do the selling themselves rather than utilizing my services… even in the enterprise market. 


This quote from a founder explains why:


Don't Skip Founder Step


– Edith Harbaugh, Co-founder and CEO of LaunchDarkly (via HeavyBit)


Simply put, the more selling you do before you hire someone, the easier it is to hire the right person to take the process and scale it up: 


  • You’ll have a better grasp on your market and ideal buyer (since you’ll have interacted with them directly)
  • You’ll have a better understanding of what it takes to sell your product (since you’ve done it yourself)
  • You’ll know what specific abilities a person you hire needs to have (because you can compare their experience to yours)


I know doing it yourself sounds intimidating (especially if you’ve never done it before), but it is possible, and it does pay off in the long run.


Can you hire someone to do it for you?


Sure. But it means you’ll have to look for someone with that specific skill set and track record of success doing so.


Scaling is not as simple as getting bodies in the door… some processes and systems have to be built to have a high-functioning, high-growth sales organization. 


So if you’re going to hire someone to do it for you, they have to be adept at building things like:


  1. Your go-to-market strategy
  2. Your process and “playbook”
  3. Recruiting


Fair warning: It’s not cheap to do it this way. In my experience, people with these skills are pricey (think VP of Sales). 


So you’ll also need to make sure you have enough runway to support the business while you’re building out your sales process. Revenue won’t be coming in right away, and you’ll have to pay salaries as your new hire develops the sales function!


What if it’s not your first sales hire?


No matter where you are in the process of building a sales team, the key is to assess:


  1. Where you are now 
  2. What’s been done up until this point 
  3. Where you want to go 


And then find the person with the right skills to connect the dots. Below are the specific things to think about that will help you do this.


4. What Kind of Deal Sizes Are You Working With?


As deal size increases, so does the complexity and sales cycle (typically). 


So you’ll want to know what kind of deal sizes to expect to find someone who is the right match in a candidate. They should have a proven track record of achievement with the deal sizes you need.


However, there’s still more to consider… namely, what did they have to do to close those deals?


It’s just as critical to understand what actions they took to achieve their success to ensure they have the specific skills to be successful with you too…


Because, frankly, not all deals of the same size are created equal!


Here are some of the specific activities you need to consider to make sure that the experience of the person you’re talking to matches what you’ll need them to do once they join your team.


5. What Specific Tasks Will This Hire Need to Accomplish to Be Successful?


If you haven’t defined what success looks like for your hire, do that first. What KPIs are focused on? What is their quota? Why?


Then, you’ll need to think about what they’ll have to do to achieve it based on everything we’ve talked about so far:


  1. Do you have a clear picture of who your buyer is yet?
  2. Have you mapped out your total addressable market or will they have to do it?
  3. Do you have a strong inbound system of leads for your sales hire to get to work on right away? Or an SDR/BDR that is doing it currently? Or do they have to generate their own?
  4. What about collateral? Playbooks? Your tech stack? Will these be in place when they arrive, or will they have to build them?
  5. How do you connect with your buyers? Do you have a process for doing that or do you need to build one?


Each of these is important to consider as you’re looking for someone to hire.  And you’ll want to ensure whoever you hire has experience doing the things you need them to.


6. What Kind of Support Team Do You Have in Place? 


Studies show it is anywhere from 5x–25x more expensive to get a new client than it is to keep an existing one.  So it’s important to have a strategy for retaining your clients once the deal is closed!


How will you continue to support your buyers once they are on board?  Do you have a customer success team/person in place to ensure this happens? 


If not, your sales hire will likely have to do that themselves!


Additionally, in the enterprise market, you’ll need to make sure your product team can support the customization and integration of your product for your buyers (I’ve never seen a product that was a perfect fit for an enterprise buyer right out of the box).


Otherwise, it will be very difficult for anyone you hire to sell your product!


7. What Kind of Sales Culture Do You Have?


Culture is the number one thing that candidates we talk to (from CRO’s all the way to AE’s) want most in their next role. So finding a match here is critical.


However, I see many startups assess culture fit by “finding someone they’d like to grab a beer with.” 


This isn’t what I’m talking about.


Real culture fit is about aligning fundamental beliefs (as they tie to your mission), your leadership, your workplace environment, and whether you’re aligned on how to approach the task at hand to reach the goals together.


It’s tricky to define, and I can’t do it for you here.  Only you know what it’s like to work within your company and what kind of person will fit there!


But the key is to take time before you begin recruiting to define what values you actually live by within your organization (not just the ones that sound good). 


Then ask questions like these below in interviews to see whether there is alignment or not:


  • “What’s important to you?”
  • “What’s the biggest misconception your coworkers have about you, and why do they think that?”
  • “What don’t you like to do?”
  • “What’s is something that happened at work this week that made you want to give up?”


The way they answer questions like these will give you a good sense of their values.


Wait… What About “Industry Experience”?


This might surprise you, but if I’m being honest, specific industry experience is less important than you think — even though it tends to be where most people look first when they’re hiring.


Don’t get me wrong… 


Having industry experience (and a network to go with it) is a great thing to have. 


However, it’s much better to hire someone who has the will, skill, and “lean in” factor to achieve the desired results in the environment they’ll face with you.


Someone who knows how to sell can learn a new industry. Someone without the right sales skills to match your needs will never get off the ground.


Final Thoughts


There’s a lot to consider here, and it’s easy to lose track of it all when you actually start interviewing candidates.


So the best advice I can give you is to take some time before you ever start the recruiting process… and use what you’ve discovered to build a system that helps you evaluate the candidates you’ll be interviewing consistently.


My weapon of choice for that is a hiring scorecard.  You can learn all about here — including a base template to start from.


Above all else, remember that making the right sales hire is about understanding YOUR landscape, what your sales pipeline and process look like today, and the desired results that define success for the person you’re hiring.


Let these guide your evaluation process, and you’ll be set up for success!