MediaRadar’s Chief Sales Officer, Jennifer Wilga, shares her favorite leadership thoughts to help you give your team the skills they need to close more deals.

Anyone who works in sales knows that there are a lot of ups and downs. 

You close a huge deal only for another prospect to hang up on you minutes later.

You can’t get a cold call to go through in the morning, but win Sales Rep of the Year at night. 

You’re frustrated that you just missed your target, but then are thrilled to find out one of your sales reps got hired to lead Sales at another company.

That last one is my favorite. 

Wait, what? 

Losing a rep is a good thing? 

No, it’s a great thing. 

Well, losing them is hard, but I love seeing them go from fresh-faced sellers to trusted sales leaders.

This is why I spend so much time figuring out how to help them optimize their days, master their craft and stay on a successful path. 

Empower Your Team—“Make them CEO of Their Business” 

If you’re a sales leader, the most important thing you can do is to empower your reps. 

When I start training a new sales rep, I begin by congratulating them. 

Congratulations, you are no longer just a sales rep. You are the CEO of your own business. 

Now, what do we mean by that? CEOs are held accountable to their quota, for bringing in sales, for owning their days and for ultimately being ready for an exciting challenge.

But we can’t throw sales reps into the deep end without sales training or support.

We have to show them that we care and that we have their back.

You know better than anyone that being in sales is hard—it’s an iterative process that requires experimentation and a ton of failure.

If your reps feel like they’re walking on eggshells, they’ll never have the comfort and autonomy needed to grow, try new tactics or reach out to that buyer. 

It’s also important that you lead by example.  

Sales reps, especially ones just getting their feet wet, will look to you for guidance. 

They’ll want to see how you respond to rejection and celebrate milestones. 

They’ll look at you to understand how to interact with colleagues and build relationships with the c-suite. 

To get the most out of your sales reps—now and in the future—assume they’re always watching and using your behaviors to pave their own path.  

Demonstrate Your Support Every Day—“I Bet On You”

To get the most out of your sales reps, you need to bet on them and give them every opportunity to level up. 

I call these Sales Vitamins—think of them as strategy sessions, workshops on how to use industry news as talking points, catchy email subject lines and success stories (and not so successful ones).

Leveling up has always been an important part of sales, but it’s arguably more important now than ever before.   

As we walk cautiously into the unknowns of selling in the post-pandemic world, the reality is that some of the strategies and tactics reps used in the past won’t have quite the same impact. 

For example, as fewer meetings take place in person, reps will have to master the art of selling through a computer screen. 

According to McKinsey & Company, “B2B companies see digital interactions as two to three times more important to their customers than traditional sales interactions.”

A Sales Vitamin that addresses this—possibly with a workshop covering video sales techniques and best practices—could go a long way in helping reps remain effective in a world spinning differently than it ever has before. 

Focus on Accountability & Goals—“Inspect what you Expect”

I live by the phrase “inspect what you expect.”

There’s no getting around the fact that a successful career in sales is all about hitting your numbers. You know, deal size, win rate and revenue.

It’s always been this way and always will be, which is why getting the most out of your sales reps banks on you taking the time to set both short- and long-term goals that take into account the dynamic nature of sales.

This means no “set-it-and-forget-it” goals. 

Agreeing on the goals is a great start, but it’s even more important to work with each rep, track their progress and adjust when needed to keep them on course.

If they’re way off course, let them know that, but also explain why they’re in that situation and how to improve. 

If they’re exceeding expectations, ask them what they believe contributed to the success and if they’d want to increase their goals. 

However your discussions go, this is an ongoing process. 

The more you talk about their goals and how they’ll pave the wave for a successful career (and help the company grow), the better off they’ll be. 

Have Fun—“I’m Serious!”

No one will ever argue with the fact that being in sales is serious business. I’d say it’s one of the most challenging and demanding professions out there.  

At the same time, no one is saying it can’t be fun as well. (Well, not nearly as many people would have said that in the past.)

Today and far into the future, getting the most out of your sales reps will rely on your ability to have fun—whether that’s in the office or through a computer screen.  

No, I’m not saying sales quotas should fall by the wayside in lieu of ping pong tables and happy hours. 

Real-business results will always take precedent. 

The point I’m making is that these results can’t lead to an obsession with trackers and at the expense of happiness. Ignoring the culture of your team is one of the biggest mistakes you can make, impacting not only your current reps but your ability to hire new ones. 

Culture is very important for employees, but we often fail to train managers in leadership. “The vast majority of corporate training covers onboarding, compliance, and the rollout of new products or systems, with relatively little on leadership development,” explains Bryan Hancock, McKinsey’s global leader of talent.

If you expect to get the most out of your sales reps and for them to give you everything in return, you have to learn how to connect with your team in effective and meaningful ways.

Of course, how you go about this will may look drastically different than how it does for your peers—and that’s ok. Every team is different, but as you think about ways to shape your workplace, consider how you can empower reps, bet on them, help them grow and most importantly, have fun.  

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