How to Hire Enterprise Salespeople
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. This is a great time to reflect and strategize so you can hire the very best people for your business when the time is right.
Up until the coronavirus pandemic: enterprise sales was the #1 role that tech companies were hiring forand employee turnover in sales was averaging just 18 months. That number will climb as our economy adjusts and recovers from the pandemic. To make matters worse, a study by Deloitte found “the cost of losing one employee can range from tens of thousands of dollars, to 2X+ their annual salary.” This says it all:
Regardless of the economic conditions, you won’t be able to hire the cream of the sales crop if you don’t develop a bulletproof hiring process to guide them in.
Employee retention is just as important as the hiring process and begins well before anyone signs on the dotted line.
Make sure you understand enterprise sales BEFORE you start the hiring process
Before you can optimize your hiring process, you need to know exactly what you’re hiring for. Enterprise sales is incredibly complex and there is a TON of confusion around what it is and what it isn’t. So let’s clear the air before going any further.
This graphic from Gartner gives a solid window into the complexity of the enterprise sales journey:
The truth is that enterprise sales is complex and ever-changing with a variety of people involved—especially when you’re just getting started or the uncertain times we’re all trying to navigate now. Having the right team of skilled and reliable people around you is table stakes if you want to build a scalable business model to stand the test of time.
But don’t be mistaken: Spinning up an enterprise sales function at a company takes at least 18 months before anything becomes repeatable, predictable, or consistent… especially now.
You can use the numbers in the graphic below as a benchmark for what to expect as you’re getting started.
So, yes, building the right team is absolutely key. But be certain that you have the proper expectations to support your team through the entire process.
You wouldn’t believe the number of times I’ve seen businesses build an enterprise team, then realize shortly thereafter that they didn’t have enough runway to support them.
How can you make the right hiring decisions when you don’t have the funding or foundation in place to let your new sales team shine?
Take the time to know what to expect (and why) BEFORE you dive into the hiring process allows you to make the most effective hiring decisions.
Before you go all in and hire too many people that are ultimately set up for failure, walk before you run to make sure you can support this model first.
The best way to do this is to understand your buyer, and hire one or two people first. Listen, learn, prove the concept and scale from there.
The last thing you want to do is hire a big team of people, without having enough territory staked out, with zero market fit, where you end up spending a ton of money burning people out while negatively affecting their careers and alienating your potential buyers for life.
It’s hard to get a second chance in this market. One of my former employers is making their fifth go at it and failing miserably, and I still hear the horror stories from my old clients who are being approached for the umpteenth time with empty promises and zero value.
Disclaimer: In this uncertain market, it’s imperative to hire if you know you can truly support the person beyond the next couple of quarters. If you’re unsure, please refrain from hiring now so you don’t have to lay someone off in two months because you rolled the dice.
Let’s talk about money
In our business, Taryn and I talk about compensation with thousands of people every year.
Along with our 20+ years in enterprise sales, we’ve scoured the data to compare and contrast what we’ve seen, to let you know what best-in-class salespeople are going to expect from you.
Before we get started, always incentivize the behavior and outcomes you want to see.
If you don’t provide concrete expectations upfront, good luck.
Depending on the market and complexity of the role, enterprise salespeople average $125K–$175K with a 50/50 split between base salary and uncapped variable.
While money is certainly a juicy dangling carrot, the savviest candidates are looking for more than just dollar signs. The best candidates care about:
Simply put, it starts from the top down. Candidates crave leadership they can get behind and that they can trust you as a leader to support them.
In a recent study, Gallup calculated that US companies lose over $1 trillion annually to employee turnover. And guess what? More than 75% of people left because of poor leadership and/or management.
This graphic illustrates the combined effect of management and leadership on an employee’s willingness to stick around.
Strong market fit
Can you prove to candidates that your product/service is a strong fit for the market? Nobody wants to join a sales team that’s floundering because there’s no demand for what’s being sold—or, even worse, that you can’t deliver.
Opportunity for growth
Top performers reach for the stars. If you can project their growth trajectory that complements what’s important to them, this is how you not only hire the best, but hang onto them.
Disclaimer: Nobody cares what your top rep made in OTE last year.
Instead, show your candidates how they’ll earn, what your territory looks like, how your buyers make purchasing decisions, how you’re adjusting expectations during this uncertain time, what your entire team performance looks like and the reality of what they can expect.
One of our most recent clients stood out to candidates because they were easily able to illustrate what their $1.4M quotas entailed, where they came from, that 50% of the team is at 200% to quota, 25% is still ramping, and 20% is at 90–120%, and the remaining 5% they could speak to why they struggled and what they’ve learned.
Honesty goes a long way.
Top qualities for enterprise sales success
Once upon a time, we recently interviewed a candidate who was a shoe-in for the job. She had all the right skills, background, credentials, client base, sales methodology—you name it.
Much to our surprise, when it came time for the onsite interview, she talked herself out of the job. The more it became real, the more we realized that what was important to her and where she was in her career didn’t align.
To put it mildly, she was risk-averse and constantly comparing our client to her current role. While that’s what the process is for, she alienated the people she met with in person to boot.
This story is important because none of this was clear in the initial steps of the interview process. We talked about the risks of an earlier stage company at length compared to where she was currently (later stage startup), but she fought for it as she was enamored with their product and seeking another “build.”
At the end of it all, everyone involved agreed this would’ve been a big miss. This is why it’s so critical to use a scorecard while digesting the details collaboratively together.
And who knows where the paths cross again in the future. No bridges burned, doors wide open = a win-win!
Be sure to focus on the strong and essential predictors when you’re screening candidates. It’s critical to be intentional. Define what success means for your top performers (NOT what you think it is or what your job descriptions say). Write it down, compare it to your job description, and pay close attention to those differences.
Remember: You’re not just looking for a person to tick all the boxes—you’re looking for someone with the right fit for your company and the stage you’re at.
That means digging deep below the surface to understand not just the things that someone tells you, but the how, why, and outcomes behind them.
It’s easy to get caught up in the “shiny objects,” but it’s the specifics behind them that make or break a candidate’s fit.
Other key points to consider:
- Look for consistency throughout their career, not just the one job that demolished expectations
- What type of mindset and level of complexity were involved to be successful in their previous roles? Does it align with your buyer journey?
- Startup friends, ask yourself if the candidate is making magic happen on their own or waiting for it to happen around them
- Are they just window shopping or are they excited and eager to commit themselves to your company’s long-term vision?
- In this market and with many people already losing their jobs, it’s important to connect the dots versus getting caught up in the “shiny objects”
The table stakes are higher than ever before. The enterprise market is dynamic, complex and ever-changing.
If you want to bring the best-of-the-best onto your enterprise sales team—and keep them—know exactly where your company stands, what your buyers demand to be successful, what your vision is going forward, what you’re prepared and able to do to support your team, and the type of people you need to bring that vision to life.
Remember: Your business is unique, your buyers are going through an incredibly difficult time and not all salespeople are created equal.
From there you can develop a systematic, organized hiring process while paving the road for long-term success.
“Data is the new oil,” has become somewhat of a trope in the tech community: a quippy statement to illustrate the vast amount of data in the universe…
Sales recruiting is broken, but there is hope in finding your perfect VP of Sales. Just follow this guide.
In just five years, she’s helped grow Stripe’s sales team to about 200 folks in the U.S. and 500 globally—that’s bigger than the entire company was when she first came on board.