Want to hire an enterprise sales team for your startup? Read this first.


A few weeks back I made this short rant on Linkedin which was sparked by a ton of proven, enterprise sales comrades I’ve talked to or known through the years who were miserable with their sales roles at their startup and want OUT.


Let’s face it, this isn’t a new issue. I’ve experienced it personally in my career and hear about it multiple times a week I’m afraid. It just happened to boil over that week.


This screams for the need to get back to basics and redefine what enterprise sales is (or more importantly, is not) and how that fits into your startup (or not).


Plus, I want to take a moment to cover some of the things you need to consider if you’re looking to jump into the enterprise “pond” as a startup. Because enterprise sales is NOT the same as working with an SMB client and you can do some serious damage if you don’t handle it properly.


So. If you’ve got your eyes set on the big bucks associated with the enterprise market, take a second to digest the following things before you jump in and potentially spin your wheels and burn through a ton of cash.


Enterprise sales is a marathon, not a sprint.


There’s a reason Usain Bolt is so much faster than your average athlete. It’s because he generates way more power with each stride and because his muscles actually react faster than everyone else’s.


However, those same techniques or qualities would never help Dennis Kimetto break the 2-hr mark for 26.2 miles. And no one would ever expect them to.


But yet, this is what happens with enterprise sales people all the time.


While the textbook definition of an enterprise level sale is often hard to agree on since every deal is unique, I am 100% in agreement with this gem of an article a la Sales Hacker:


“A complex [enterprise level] sale involves multiple stakeholders, a longer sales cycle, and a high degree of perceived risk on the part of the buyer.”


This can mean many things to many people/organizations. But in plain English, here’s what that roughly translates to in the dynamic world of high-tech startups (where I’ve worked for years):


  • 9 to 18+ months to close
  • Pricing often happens on a yearly basis, not monthly with some discretionary budget that could be applied to a pilot if you’re lucky (side note: are you setting goals around MRR when it should be ARR?)
  • Enterprise buyers are highly risk-averse because no one wants to rock the boat and because their butts are on the line if something goes wrong
  • An average of 6.8 people involved in the decision-making process (up 25.9% over the last 2 years)


With that said, I hope the following is clear: this is NOT transactional or cookie-cutter…you can’t just drop your demo in your buyer’s lap, riddle them with scripts and templates from Salesforce, collect a big check, and walk away.  


Enterprise sales is about crafting a custom solution to solve your customer’s problems rather than giving them a “one size fits all” product. And that takes a ton of preparation, creativity, and high-level strategic thinking to pull off.


Plus, your sales reps need exceptional people skills over a long period of time to close a deal of that magnitude.


And spoiler alert: this process doesn’t stop either. A wise beyond his years, butt-kicking enterprise sales top-performer recently told me the secret to his success was maintaining a constant quest to enhance their customer’s performance. So even when the ink is dry on the contract, there’s still more work to do.


Which brings us back to the problem that causes most proven enterprise sales people to fail: being pushed to operate like they’re running the 100m when they’re in it for the long haul. Square peg, meet round hole.


Bottom line: enterprise clients are expensive and time-consuming propositions requiring a lot of strategic TLC. So if you want to play in the enterprise space, take a second to wrap your head around the investment it’s going to take to get there.


And then…


Do your homework, and set your expectations appropriately.


I get it. You like the money and opportunity that the enterprise market holds, and so does your board. But take it from me, if you don’t take the appropriate measures before jumping in, the odds of your venture into this market crashing and burning are significant.


In my pre-ATP sales life, I was hired to be the first enterprise sales person to build out the function for a thriving startup with some serious legs (my area of expertise).


However, while the senior leadership team loved the idea of what enterprise sales could do for their business and the big logos I had in my Rolodex, they didn’t understand their marketplace, take the time to understand their buyer cycle, or realize their product wasn’t mature enough to support a Fortune brand.


Fast forward to post-hire, and they also refused to iterate on the product and provide an impactful marketing strategy. And ultimately, the ROI with the clients I had worked so hard to bring in was dismal! It was a total disaster (think 70%+ churn) and it pushed me over the edge to exit the company even though I was their #1 rep.


Zach Hatterick Headshot

"Now my buyers see me as a valuable person to know."

– Zach Hatterick, Account Executive


The good news is, this all can be avoided if you understand what enterprise sales requires and set realistic expectations based on your product and market.


So if you want a piece of the enterprise pie, here are some of the most important questions you need to answer in detail before you ever think about hiring (if you’re looking for a job: ask prospective employers these during the interview process and run for the hills if they don’t have solid answers):


  1. Have you defined the marketplace?
  2. Do you understand the needs of your enterprise customer, their problems, what’s important to them and the landscape in which they operate?
  3. If your customer had a headache, would they regard your product as a “vitamin” or a “painkiller”? Are you prepared to iterate on the product to support the complex needs of your buyer?
  4. Do you understand the buyer journey and what the sales cycle really looks like?
  5. What is the expectation from the board and executive leadership team on the timeline to build this out and will it work with the buying cycle you’ve defined?


Don’t have answers to these questions? Time to get to work.


It doesn’t matter how talented your sales team is or how much effort you pour into your product–if you don’t have a clear understanding of your customer, their buying cycle, their appetite for what you’re bringing their way, or the competitive landscape, your sales are going to suffer for it and your team is headed out the door.


Remember…the marketplace always speaks louder than you, your board, or your product. So check with it first. Test your product out in the real world and get a feel for how your target enterprise customer buys.


Then find someone to help you sell it.


Want to know more about how to get to know your enterprise market? This is the best book I’ve ever read on the subject.


This IS doable. Just proceed carefully.


My goal isn’t to scare you away from the enterprise market, but rather to help you make sure you understand what you’re getting into and how to dominate inside of this very rewarding channel.


I don’t want you to find out your product isn’t suited for the enterprise market (a real possibility) or that your runway estimate is too short after you’ve already hired an enterprise level sales person. It’s a waste of time and money and creates a negative buzz you want to avoid at all costs.


So just keep in mind, the requirements are completely different. Like you don’t catch 30 ft. sharks with a fishing pole and a rowboat, you don’t land enterprise clients with the same techniques you’ve used to close deals with SMB customers.


Have friend or colleague who is trying to get into the enterprise market? Share this article with them As I like to say, “sharing is caring.”