Leading a sales team has arguably never been more challenging.
Everyone, from your reps to potential leads to the folks on the deal desk, is navigating the new world of remote- and hybrid-work and the latest tech and tools while worrying about kids and partners and parents and friends.
The rate at which many companies — your own and your customers' — are changing just ups the complexity for sales leaders.
As companies grow and mature, sales teams naturally evolve—and so too must their leadership. We often hear about the importance of sales leadership, but the fact is, leading a sales team looks different across the stages of an organization’s growth. And sales leadership requires unique mindsets and behaviors to support the growth of the company, the growth of the team, and the growth of the individuals.
Brad McCracken, BetterUp’s Global Vice President of Sales, knows well that the right mindsets and behaviors are often overlooked in favor of sales tactics and tools. He also knows what it takes to lead a sales team — whether that’s from a startup’s earliest days to exponential growth or, in his prior life, in more stable and mature organizations.
We caught up with Brad for an interview on the importance of sales leadership and the key mindsets and behaviors that sales leaders need to help their teams succeed at every stage.
Maggie Wooll: How is the growth of a sales organization related to sales leadership? What changes to mindset and behavior do sales leaders need to make to have a positive impact on their organization?
Brad McCracken: The big differentiator in successful leaders is your ability to be an agile learner. If you can pivot and change and understand that the job is going to be different every month, then you’re more likely to be successful in a high-growth startup environment.
In the early days of a startup, before an organization has a robust marketing machine and word-of-mouth recognition, the job of a sales leader might be back to basics — it’s leading call blitzes and direct hands-on involvement in a lot of deals.
But as the team gets good at the basics and the pipeline starts to fill up, people start to learn more on their own. From there, the job of the sales leader continually evolves. When you reach a new level of growth, the job becomes more about optimizing, operational excellence, and world-class enablement. So, agility is key.
In my experience, cultivating trust is also important. There was a time when I could be involved in basically every major deal, but as growth scales, I simply cannot be involved at the same level.
As that growth happens, a leader has to trust the team to do what needs to be done. That means also being pretty confident that your team will know what needs to be done, so cultivating trust is also about giving people opportunities and clear guidance along the way so that they are constantly developing. And treating them in a way that gives them confidence and empowers them to figure out what the right thing to do next is.
This is something I’ve seen front-line sales managers really struggle with. But when they get it right? The team soars.
Another critical capability is adaptability. If change freaks you out, you're going to have a problem because every sales organization is going to experience some level of transformation.
We’re seeing that now with the way the world has changed — with hybrid work. The days of sitting in an office and being able to know what everybody's doing all the time — that’s not happening anymore. So if you were a masterful micromanager, then you're in a tough place right now. It's not easy to micromanage when you're sitting on Zoom calls (and I'd say it’s not very productive even if you’re sitting right next to them).
Successful sales leaders are people who can lean into change, and get excited about that. They confront change and new challenges and say, “Let’s go figure this out.” That's a big difference that great leaders have in common.
MW: In the later phases of the pandemic, sales professionals and sales leaders are turning over at a significantly higher rate. How can we better support sales leaders and their teams to curb turnover?
BM: Even before the pandemic, turnover was high in sales—and now it’s even higher. One of the biggest reasons for turnover is people feeling they don’t belong. People won’t stay if they don’t feel like they belong.
Sales leaders historically have fostered belonging through office meetings and happy hours. And now, that’s harder to do with hybrid teams—it’s not even an option in many workplaces. The pandemic changed a lot of the old, familiar ways of doing things. How we build inclusive teams is one of them. Sales leaders need to really focus and be deliberate about what they are doing to build an inclusive environment where people feel like they belong.
For most companies to succeed, you’re going to have to sell to and support a diverse range of people. Your own team is going to have to be more diverse.
When you have a very diverse team, you have to make sure that people from different backgrounds feel like they belong in the business. That requires more than just calling people out on a call and asking them to weigh in. A sales leader has to make space for people to feel safe engaging in conversations and getting feedback. Sales leaders need to be trained in how to do that.
If you don't feel like you belong and you're stressed, then you're probably not going to be here for long. And sales is a stressful environment because performance matters. Sometimes that's tough. When you tie that into a sales organization, you’ll find employees are often dealing with a high amount of stress. So helping people reduce stress and manage their emotions is really important.
MW: How can leaders reduce stress for their employees, especially considering that many leaders themselves feel pressure to hit benchmarks and struggle with managing their own stress?
BM: Making sure people feel like they belong and keeping a pulse on stress really go hand-in-hand. You have to check in on how people are doing. Little things, like creating a fun environment, bringing a sense of optimism to the job, and keeping the team focused on the right things—all of that can help.
But most importantly, you have to honor the one-on-one time with your team members. Too many leaders don’t show up for their one-on-ones — that’s a mistake. You have to engage and have that personal connection with your team to understand their individual motivations. You're just not going to get that in a group conversation.
For example, I just finished my Friday call — there are 100 people on that call. In a massive Zoom call, there’s no way for me to know if individuals are confused about our latest GTM guidance, new product features, or territories. I can’t tell if they’re overwhelmed and stressed or full-on burnt out. You only learn that from individual time.
For a sales leader, that means you have to manage your calendar effectively to make time for those one-on-ones, and then you have to show up for those calls with the right mindset. Sometimes it's about listening more than it is talking. That’s how you help people feel like they belong.
MW: While some organizations are struggling to retain their sales talent, or even up-level their current talent, others are in hypergrowth mode. They can’t hire people fast enough. What should they be thinking about from a sales leadership perspective?
BM: Even if you're growing like crazy, even if things are going well, sales leaders need to be careful. Because sometimes with tremendous growth, you see people struggling with burnout and eventually leaving.
When numbers are strong, that's great. But there can be undue stress within the organization that you're not seeing. And it's those future blind spots that you have to worry about.
We’ve seen that before in organizations in hypergrowth. In an A/B test of director-level sales managers where one group received coaching and one group didn't, the group that got coaching did way better, to the tune of an extra $10M in bookings for those teams, in one quarter alone.
Coached sales managers saw a 20% increase in the value of their opportunities relative to the same quarter a year prior and a 60% increase in the number of team members that achieved quota relative to the same quarter a year prior. The non-coached group saw a decline in the value of opportunities and no change in the number of team members achieving quota. The coached group also reported more clarity and focus.
Even though everyone overall was doing pretty well prior to coaching, that extra support helped them keep going and reach even higher. That helps create sustainable growth, it keeps people engaged in their work, and it helps you avoid losing employees because they’re too burned out to continue.
MW: What advice would you give across the board, to sales leaders in organizations at any stage? What’s an important factor that everyone tends to overlook?
BM: No matter what stage an organization is in, sales leaders need to put more focus on their middle performers. There’s a common issue in sales where 20% of your account executives are generating 80% of your revenue. And most sales leaders focus on the best and the worst performers, but really that middle group is where you should spend your time.
It's much easier to make a middle performer into a high performer than to start from scratch. When we can get those employees to perform at a higher level, that’s where you can make a ton more money. And often those middle performers have great potential, but there’s a missing link.
In some cases, it’s a mindset issue. Maybe they just don’t see themselves as successful. They’re reluctant for some reason. If you can find out what’s missing or what barriers they have, and work to address those issues, you can help them elevate their performance and reach the next level. When you see that happen, it’s such an awesome feeling.
Learn how BetterUp’s Sale Performance Coaching can empower your sales leaders and teams.