You Might Be Ruining Your Career and Not Even Realizing It

Let me start this off by clarifying what I mean by “ruining your career”. If you picked sales as a career, it says a few things about you. You’re a risk taker, money motivated and work is life. With that said, the WORST thing you can do as a sales rep isn’t missing your quota, it’s picking the wrong type of company.

Simply put, you need to pick companies that sell a true enterprise wide application that will allow you to sell deals with a high ACV (average contract value). If you don’t, you’re never going to make a life changing amount of money, you’ll just be a piker (a gambler who only makes small bets). The reasoning behind that is simple, higher ACV demands higher commissions and more skill. It’s also much riskier operating in an enterprise sales environment. Convincing a company with 10,000 employees to change their software strategy is incredibly challenging. It’s easy to sell a $1,000 widget that only impacts a few employee’s, it’s hard to sell a $1,000,000 enterprise wide application that changes the way 1,000’s of employee’s work. You work in sales because you’re a risk taker and money motivated though, right?

If you’re reading this now and you work in sales at a company that offers a point solution with a low ACV, GET OUT!


Keep in mind, nobody starts their career closing 6 figure and 7 figure deals. You’re likely going to start closing really small deals, likely in the thousands of dollars range. That’s completely OK! As long as the company you’re working for has a path for you to become a true enterprise sales reps (6-7 figure deals) then you’re in good shape.

There’s a reason why companies like Salesforce, Adobe and Medallia consistently produce sales reps with $1M+ W2’s, and it’s because of their ACV. Do you think they want to hire a guy / girl whose only sales experience is in selling small deals? Hell no.

Now you might be thinking, “how do I get into an enterprise company if I work at a company with a low ACV”? To be honest, it’s going to be challenging. You are going to have to accept that you may need to pay cut in year 1 and an initial step back in your career so you can take 2 steps forward. It’s going to be hard, really hard, but if you commit to it and you’re successful, you’ll be wondering why you didn’t do this earlier.