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How to Be a Sales Leader: 5 Field-Tested Ways

How to Be a Sales Leader: 5 Field-Tested Ways

This post was originally written in 2017 by MediaRadar’s sales champion, Jen Wilga. The content was updated in March 2022.

Once upon a time, early on in my sales career, I earned Sales Rep of the Year. It was an incredible honor that I’ll remember forever. 

But since that day, I’ve had the pleasure of leading a sales team and seeing my sales reps receive the same honor. No amount of personal accolades will overshadow the feeling of pride to watch my reps achieve their dreams.

Through it all, I’ve learned some things about how to be a sales leader. Just like all leaders, I’ve had to adapt over the last two years. But even amid all the change, these five key lessons hold true.

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How to Be a Sales Leader in the Modern Workplace

1. Bet on your team and build a healthy relationship with reps

“Bet on them” is something I often say and firmly believe other sales leaders should say as well. 

For better or worse, being a sales rep is hard. 

Sales rep turnover hovers around 35% each year—which is expensive and unnecessary. But the problem isn’t usually the capability of the rep. It’s a problem with the system and the work culture they’re in. 

Bridge Group surveyed more than three hundred fifty B2B software companies: Of the top ten reasons sales reps left a position, 60%-80% left due to lack of connection with leadership or the incompetence of leadership. 

Many cited a toxic sales culture and an incompetency of sales leadership team when it comes to decision-making, coaching or recognition.

Your connection with your sales reps matters—a lot

The first step to being a sales leader is to believe in your team. Then you can build the right systems and equip them with the tools necessary to succeed. 

There will always be rebuttals and lost deals. Hang-ups and uncertainty. Doubts and missed opportunities. 

Betting on them—and letting them know that you are—is the best way to instill confidence and give your sales reps the mindset to succeed. 

2. Lead by Example

No one wants to follow an armchair leader. It sounds obvious, but I still see some sales leaders “leading” from their desks and wondering why their teams aren’t hitting their numbers. 

The best sales leaders take charge and lead by example. Whether it’s by doing role plays with the team, cold calling prospects, attending trainings or sitting through meetings, leading by example is one of the best ways to be a successful sales leader. 

Show your reps that you’re just as invested in the process as you expect them to be. Respect is earned by jumping in the trenches alongside them. 

Plus, doing so is a great way to sharpen your skills and learn the obstacles your team faces. It’s a win-win.

3. Invest in Learning 

Industry trends and buyer needs shift frequently. 

For this reason, the best sales leaders constantly look for learning opportunities for their team—think strategy sessions that cover new selling techniques, ways to use recent industry news as talking points during pitches or catchy email subject lines you’ve had success with lately. 

When selling ads (especially during a pandemic), you need to keep on the latest data. It’s essential to have a tool that easily helps your ad sales leaders learn about:

  • Regional trends
  • Industry patterns
  • The latest ad tech and emerging media developments
  • Brand spending information across ad formats, including noteworthy shifts
  • Creative campaigns
  • Competitor advertising spending and strategies
  • Key decision makers, their past professional history and their current contact information

The sales world is always changing, so data and learning how to apply the data insights to the sales process is key. 

4. Focus on Goals

The only way to make sure your team executes your plan and moves toward your targets is to “inspect what you expect.” 

Do this by setting realistic targets for reps and then working toward them together. As you sync with your reps, have pointed conversations about their progress, what’s working and what’s not. 

Then, identify ways they can improve and explain how those improvements will positively impact everyone. When you create buy-in and show the reps that what they’re doing matters, good things happen.

5. Have Fun

I had a job early in my career that I couldn’t get excited for. The feeling of dread would start on Sunday nights when I’d start feeling sick to my stomach. I remember this feeling vividly and have vowed to do everything to make sure my reps never have to experience the feeling. 

This is why I take so much pride in creating a culture where people are valued, operate with integrity, get better each day and have fun. 

Don’t get me wrong, goals are important, but that’s not the only element of a high-performing sales team. If your reps aren’t happy, they won’t perform at their highest level, which is especially true today as we usher in younger sellers who value non-financial benefits more than anything. 

Leading the Next Generation of Sales Reps

When we think about how to be a sales leader, we need to be invested in others, willing to learn and adapt to new sales environments.

If we’ve learned anything from the COVID-19 pandemic, it’s that the world can change quickly. 

With the blink of an eye, we went from an in-person world where face-to-face interactions with buyers were normal to a reality where they’re few and far between. That’s not going to change. 

More than three-quarters of buyers and sellers say they prefer digital self-serve and remote human engagement over face-to-face interactions. While it’s impossible to predict the next big change, one will come and when it does, the best sales leaders will find ways to keep their team on a successful path forward.

As the sales world evolves to meet the new normal—one even more reliant on technology—sales leaders will have to reevaluate every aspect of their day and determine if what they’re doing still meets the needs of their reps and the company. If you can continuously do that, the answer to “how can I be a good sales leader” will be “keep doing what I’m doing.”