Can I Get A Do-over? My 5 BIGGEST Sales Mistakes

There is nothing more exhilarating for a startup than closing deals.  Hitting sales targets, beating competitors, and disrupting a market is what drives us.

I’ve had the incomparable experience of helping grow a sales organization from the ground up.  In 3 years we grew the business from 1 to 40 sales team members and grew our customer base from 20 to almost 2,000.  In that time I’ve made a number of mistakes that were extremely detrimental to the business.  In hindsight, I should have seen what was transpiring.  I should have gotten additional insight from advisors.  I should have read more.  I should have pulled my head out of the weeds.  I didn’t do those things however, and the result was the joy of failure.  I learned a great deal from these mistakes and they will undoubtedly stick with me.

Here are my 5 biggest mistakes that could have changed the outcome of our business:

  1. Hiring Bodies

We grew fast and needed to hire a large number of inside sales reps.  We didn’t have a recruiter and we had numbers to hit.  I settled.  I hired people that didn’t blow me away.  I hired bodies, not superstars.  Guess what?  They turned-over and I had to hire all over again.

2. Churn? What Churn?

When I realized that customer churn had become an issue, it was too late.  I was blinded and focused solely on new business and neglected our current customers.  I should have hired someone in a Customer Success or Account Management role much sooner than I did.  I also should have built out a defined process for this area and team.  Because of this, churn took a front seat as our number one challenge for a few excruciating quarters.

3.  Sales Process and CRM

I spent a few years consulting and building sales process for clients.  I should have known better than to not define our sales process and match that up with the pipeline stages in our CRM.  It wasn’t until we were at about 20 sales people did I really dial in our process.  The outcome of that delay was inconsistent sales behavior and an unorganized CRM.

4.  Discounting

Setting prices low or heavily discounting and thinking that you will be able to increase current customer prices is extremely difficult.  We have gone through a number of pricing iterations.  I regret not pricing our solution based on the value it provides early on.  It took me a long time to be comfortable with walking away from deals.

5. Define Your Market

Our first target market was small and mid-sized businesses.  Yup, it was that specific!  The spray method didn’t work out too well for us.  We then shifted all of our focus to one, very specific and defined target market.  This shift of focus is one of the biggest attributes to our success.