4 lessons I've learned in sport sales

by aaron klein - manager, inside sales at marquee 360 and the chicago cubs
December 17, 2019

In the six months since I transitioned from a sales representative to a sales team manager, I’ve had time to reflect on my successes and failures and consider ways to help my team avoid those same mistakes. Most of the shortcomings in my sales career fall into four categories and can be easily avoided if you fully commit to doing so.

1. Prioritizing business knowledge

Most people reading this probably consider themselves a sports junkie. They know player stats, they follow the “experts” on social media, and they listen to podcasts. Far too often, I got caught-up in looking at stats or checking out our upcoming series and the potential pitching matchups. Do you think my prospects cared who was going to be on the mound for our opponent? Of course not. Our clients and prospects are interested in knowing how our product will help their business.

Take some of the time you spend diving a little too deeply into the sports realm and shift that focus to gaining a better understanding of the business environment of your city and region, and new initiatives of the companies you work with. Swap out your Twitter time for LinkedIn. Connect with your clients and top prospects, and browse your feed daily looking for updates. When your client signs a new business deal, they don’t immediately think, “we need to celebrate this with a suite!” Grab your client’s attention by catching their LinkedIn post and sending them a congratulatory note. A highlight of my sales career was closing a suite in this exact situation. However, I likely missed far more opportunities by spending too much time on unnecessary sports knowledge, at the expense of developing a deeper understanding of the business world.

2. Setting expectations

We always want to provide best-in-class customer service and fulfill client requests, but sometimes that’s simply not possible—at least not in the moment.

Booking a sporting event is different from other experiences, and a far cry from the typical purchasing decision. While we understand our limited inventory and the speed at which our products sell, we often fail to accurately relay that information to our clients so that they may set appropriate expectations. Make sure to end every call with the expectations and next steps for you and your clients, so neither party is moving forward based on assumptions.

When we have clients that make requests we cannot accommodate, we can’t be afraid to say “no.” Before I started my career in sales, I worked in operations, where my job was always to find a way to get to a “yes.” During my first season with the Cubs, I struggled with telling clients I couldn’t provide exactly what they were asking for. I’d say things like “I’ll see what I can do,” even when I knew I couldn’t do anything. This just delayed the inevitable and slowed down the sales process. The solution? Have the confidence to acknowledge their request, identify their true need and then find an alternative way to deliver on that need.

3. Attention to detail

Sales is a numbers game. We have to work quickly and efficiently in order to maximize our outreach and grow our sales pipeline. We must balance this speed with accuracy in order to be successful.

We often rush through emails and make typos. Sometimes, these slip-ups have a small negative impact on the perception our clients have of us. However, there are times when a mistake can result in an errant price quote that leads to backlash from a customer. As you move up the ladder in an organization, consequences of a mistake can become more significant. It’s critical to establish the habit of a thorough review of your work. This is something I still focus on every day.

A sale can entail hours of work, including a multitude of phone calls and building proposals. It simply doesn’t make sense to rush through the software logistics of locking it in, just to save a couple minutes. A low point in my career was having to explain to a client that their event had been double-booked due to an oversight in our inventory system. While we were able to identify a solution that made the client happy, my lack of attention to detail jeopardized the relationship and ended up costing me at least another hour of work.

Efficiency is a key to success in sales, but we need to understand when to shift gears and slow down.

4. Sales is a team sport

In sales, our career advancement often depends on being towards the top of our team in sales and call volume. However, that doesn’t mean we have to put ourselves on an island. Sales is rarely a zero-sum game where the success of a peer limits your opportunities. In my first year in sales, I constantly checked call and revenue numbers, and felt jealous when I didn’t achieve at the same level as my peers. During my second season, I made a conscious effort to change my mindset – to celebrate the accomplishments of my teammates.

At the Cubs, one of our corporate values is “Team First.” How can we incorporate this into our daily life as a seller? Small things like sharing a successful email template and other best practices or inviting a colleague to join you at a networking event. When you hear a teammate having a difficult back and forth on a call, offer your support, or be a sounding board for potential solutions to the issue.

Don’t be afraid to ask other sellers or your manager for advice. I remember feeling that asking for help was a sign of weakness, and that others would see me as less skilled if I couldn’t resolve situations on my own. I now appreciate that some of my top sales wouldn’t have happened without learning from my peers--whether it was actively going to them for advice, or keeping my ears open for their sales tactics. If you remember that sales are a team effort, and approach your colleagues with that mindset, you’ll have far more success in your career than you ever could in isolation.

Mistakes will happen. It’s how we react to and overcome them that determines our future. As Denis Waitley wrote, “failure is the fertilizer for success.” I hope that those reading this can learn from my mistakes to help improve their careers as sellers.


Aaron Klein is the Manager of Inside Sales with Marquee 360 and the Chicago Cubs. He’s been with the club for more than 3 years and has grown from their Sales Development program into leadership in just a short time. He holds both Bachelors and Masters Degrees from Cornell University and he’s also a mentor in theClubhouse. You can connect with Aaron for a call by going here.