The biggest lesson I learned in my sales career

Poignant lessons from our sales leaders.

By Rachel Serpa

Published May 17, 2017
Last updated September 1, 2020

“Life is a succession of lessons which must be lived to be understood.” – Helen Keller

It’s probably fair to say that we can all think of a time in life when we learned something especially profound that significantly impacted the way we conduct ourselves or understand others. As painful or intense as these lessons can be, they are necessary to grow and improve as people and professionals. Even better, sometimes we are taught these lessons through positive experiences, or as a result of watching or listening to others.

If you’re a sales professional who is serious about honing your craft, chances are that you will encounter several of these lessons along your career trajectory. So, we’ve asked some of our sales leaders to share the most poignant lessons that they’ve learned over the course of their sales careers.

Justin Hunt, Account Executive

I lost a deal a couple years ago that still sticks with me. I spent 4.5 months working it and it would have easily been a top 5 customer for my company at the time. To make matters worse, I had to call my CEO and interrupt the last day of his vacation to notify him. There were a few learning lessons from this experience but I'll talk about the most notable.

I had worked this deal hard and I thought we were in a great place. We had access to power. We had met all the decision makers. I had a kick @$$ champion feeding me data on our competition daily. What I didn't anticipate were the traps the competition had set for us and how it would impact the opinion of 2-3 key people.

After pulling ahead to the #1 spot the week before Thanksgiving, I could feel us slipping behind in early December. The line of questioning was clearly indicative of a particular competitor’s playbook. I scrambled to get answers and worked primarily through the chief influencer, while getting some inside intel from my champion on the side. When I got the call on December 31, it hit me like a blow to the chest. I debriefed with my CEO and we did a post mortem.

As I said, there were a couple of errors, but the most glaring was that we didn't fully understand how they were going to make a decision. Yes, I had a lot of people in my corner. But there was one group that I never really spent much time with. And ultimately their gripes were larger than the kudos I received from my supporters. I had access to the chief influencer but he democratized the decision to the team. I had a great champion, but he lacked influence and had less insight into the team against us.

If I had a complete and full understanding of how they were going to make a decision, I could have met 1:1 with the 3 people who were against us and likely won the deal. You can have all the right pieces in a deal, but if you don't know PRECISELY how the decision is going to be made (by whom, on what date, in what format, etc.), you're setting yourself up for failure.

Kyle Osterman, VP of Enterprise Sales

I have had the good fortune to work in sales and sales leadership with several world class companies over my 30+ year career. I had early exposure to some of the finest sales minds in the business, including sales training pioneer Neil Rackham and forward thinking sales training programs that include SPIN Selling, Solution Selling, Strategic Selling, the Challenger Sale, and Force Management. All of these programs offer critical skills and strategies around the successful management of a sales cycle. I took so much from these investments.

However the single mantra that provides the most meaning in my professional and personal life is simply, “Think it to bring it!” Sales professionals need to believe in their ability and their solution/product/company/service. They’ve got to know in their heart that they are 100% committed to assisting the client in improving their business outcomes based on the products and services they are presenting. This positive attitude will manifest into success. As Henry Ford said, “Think you can, think you can’t; either way you’ll be right.”

Jessica Jonsson, Account Executive

While in a sale cycle, whether it's an entirely new logo or I’m expanding my product to other departments, I always have a couple of contacts that I maintain a strong relationship with. In theory, this sounds great, but it also can become your blindside.

It’s great in that they will hopefully point you in the right direction, push for your product, share information privately with you and be a part of closing the deal. However, it’s easy to be blindsided if it turns out that your “champion” does not have the influence or run in the internal circle necessary to get the deal across the finish line, or does not understand the ecosystem as well as he/she portrayed. What’s even worse is if they aren’t as loyal as you thought.

While I still develop these strong relationships today, I have learned over time to continuously test them and make sure that they’re the real deal. This can be done by asking tough questions, involving other members of my team, requesting sponsor meetings, etc. I’ve also learned to take a step back from a deal to see what’s missing and to identify the exact role a champion plays in the overall picture. Otherwise, the very deal that was going to help get you get to quota may fall apart and leave you wondering what went wrong.

Michael Logan, VP of Sales

Two impactful lessons come to mind. The first is that I can create my own destiny with a great outbound plan. Feeling great about your product and wanting to tell the world about it is one of the most fun aspects at the job. I was taught how to develop a Destiny Plan for my franchise during my time at Aprimo, and through effective targeting and a focused multi-channel outreach, was able to help 22 companies over the span of 3 years improve their operations.

Key learning number two was learning to translate the excitement around a great meeting and product fit / business issue to a financial return for the customer. Sharing with clients that there is a process to get them from their "as is" process to their "to be" state and what that means to the stakeholders and how to quantify it is key. In other words, should they buy my solution, improve the cafeteria or pave the parking lot? What’s the best investment for them and how can I prove that it’s mine?

Learn from the Best

Often the best way to learn is from the sound experience and advice of others. For more sales tips and strategies like the ones shared in this post, subscribe to the Zendesk Library below.

This post originally ran on the Base blog. Please visit if you’d like to learn more about Zendesk Sell.

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