How to Retain Your Sales Superstars (and Stop Them From Being Headhunted)

Timothy Carter
May 14, 2024

Sales teams tend to have a diverse mix of people.

They may all have similar backgrounds and follow a similar methodology, but they're all unique individuals with unique strengths and weaknesses.

Accordingly, major companies typically have standout sales “superstars” capable of landing humongous accounts and keeping them indefinitely. They're the most valuable members of your team, by far, which is great – but it also introduces a vulnerability.

If those sales superstars choose to leave, either because they find a new opportunity or because they no longer enjoy their work, it will leave a massive, gaping hole in your sales strategy.

So what are the best approaches to retain those sales superstars?

An Analysis of the Sales Rep Retention Problem

Let's take a look at the sales rep retention problem from a high level.

The superstars on your sales team are simply better than everyone else. This is probably due to a combination of factors, such as getting more done in less time, having more charisma to persuade others, or utilizing a more eclectic knowledge of your clients’ needs.

Whatever the case, these are the people who can land the big accounts. These are the people disproportionately responsible for your sales team hitting its goals for the quarter. These are the people who keep the revenue flowing.

In other words, they are massive value creators that you can't afford to lose.

Your top sales reps also succeed in retaining your best clients. And while retention is typically cheaper and less effort intensive than acquisition, you can't afford to neglect it as a critical part of your sales strategy. If your top sales reps leave, they may take some of your clients with them, or motivate other clients to jump ship.

That means in addition to losing revenue generation potential, you'll also be losing a chunk of your client base.

So your sales superstars are valuable. Why is this a problem, exactly?

It's because everyone else knows how valuable they are.

Your sales reps know how valuable they are. Your competitors know how valuable they are.

This opens the door to two distinct paths for departure.

First, your sales superstars could choose to leave on their own volition. Even if they're making a lot of money and are succeeding in their role, they may feel pressure to change roles, change companies, or drop out of the workforce altogether. And it's much more common than you think: it’s estimated that 25 percent of sales reps are planning on leaving within the next 6 months.

Second, your sales superstars could be headhunted and recruited by your top competitors. These reps already have knowledge, experience, and proven capabilities, and they won't need much training or education to thrive in a new role. This makes them highly attractive targets for recruiters, who will often be willing to offer those reps more compensation than you currently do.

Obviously, every sales superstar is different, and there are many complexly interwoven motivations that could cause each one to leave. But the better you understand those motivations, the more likely you'll be able to retain the sales titans who make your marketing and sales strategies successful.

In the sections that follow, we'll be analyzing various individual problems that are likely to affect your sales reps. After that, we’ll summarize the generalized strategies that can help you resolve many of these problems simultaneously, enabling you to retain your top sales staff.

The Burnout Problem

First, we have the burnout problem. If you work in a role long enough, eventually, you're likely to grow tired of it. This problem is compounded by jobs that are especially difficult, stressful, or time intensive.

Sales can be difficult, stressful, and time intensive simultaneously, so it's no wonder why so many sales reps have one foot out the door. If one of your reps is disproportionately responsible for the success of the business, and they have more responsibilities than their peers, they may feel even more burnout.

If the problem gets bad enough, they may leave on their own. But even if the stages of burnout are just starting, a sales superstar will be much more likely to leave if contacted by a recruiter.

So what can you do about this?

·       Proactively recognize (and address) the signs of burnout. Some burnout signs are obvious. Others are less so. If you wait until your sales rep is having a panic attack or showing up to work with permanent bags under their eyes, you're going to lose them. Instead, you need to be on the watch for burnout signs early and often. Does this person seem less engaged with their work? Are they more irritable? If you notice these signs, take the time to address them.

·       End toxic work expectations. American companies sometimes pride themselves on hard work. This alone isn't a bad thing, but it can become toxic in high doses. If you expect your employees to work through the weekend, work long hours, respond to emails late at night, and tackle other burdensome responsibilities for the sake of proving what a hard worker they are, you're effectively pushing your top workers away. End these toxic work expectations and give people more flexibility.

·       Encourage, rather than merely tolerating, time off. The best way to prevent or stave off burnout is through time off. Many Fortune 500 companies readily allow their employees to take time off work for occasional breaks and vacations, but there's a big difference between tolerating and encouraging time off. Don't just allow it under extreme circumstances; actively push your top sales members to step away from the job and destress.

·       Prioritize meaningful engagement. Burnout is also solved with enough meaningful engagement. If your sales rep is consistently engaged with their work, they probably won't be motivated to leave anytime soon. Different people engage with their work in different ways; some people want more challenging work, while others want more creatively stimulating work, for example. Your job is to find what motivates your top employees and give it to them more specifically.

·       Shake things up. Excessively repetitive routines can cause anyone to experience burnout, even if they generally love the contents of those routines. That's why it's important to shake things up from time to time; cycle through different responsibilities, give your sales rep exposure to new environments, and help them feel like every day at work is truly unique.

The Compensation Problem

Less commonly, sales superstars leave because of compensation issues. This doesn't necessarily mean you're underpaying them, but it does mean a competitor is willing to pay them more. If a sales rep notices a discrepancy between their actual value to the organization and what they're earning, they're going to be motivated to close that gap, no matter how much you're paying them nominally.

That's why it's important to:

·       Stay tuned to the competition. Keep a close eye on the sales strategies of your competitors, to whatever extent you can. How much are their top salespeople being compensated? How much are they offering when headhunting others? Can you stay competitive with them?

·       Increase pay and/or commissions. The most direct solution to this problem is to increase pay or commissions for your top sales performers. If this sales rep is as valuable as they seem, it will probably be worth it. If it's out of budget, you'll have to come up with an alternative strategy to make it more worthwhile to stay in your organization.

·       Consider adopting new benefits. New benefits, such as more robust health insurance or better retirement programs, can incentivize sales reps to stay, even if their core compensation doesn't increase. But again, this isn't going to fit all budgets.

·       Offer flex time and other intangible benefits. If money is tight, consider rewarding your best sales employees with intangible benefits like flextime, extra time off, dedicated parking spaces, or other smaller rewards. They may not seem like much, but they can seriously add up, especially in combination with other strategies in this guide.

The Culture Fit Problem

Sometimes, your sales superstars become motivated to leave because of a culture fit problem.

Unfortunately, there isn't much to cover in this area. If a sales rep has been with your organization long enough, you can rule out culture fit as a problem (unless you've undergone a serious change in your workplace culture since they arrived). After all, they wouldn't have stayed this long if they had a problem with how you run things.

Also, if a sales superstar does begin to grow resentful of your workplace culture, there isn't much you can do. Unless you're planning on uprooting and changing your entire workplace culture for the sole sake of this individual, the better path for both of you might be allowing the departure to take place.

The Autonomy Problem

Many employees rank autonomy as one of their most important priorities, and a major goal for their career. People generally want to be in control of their own work; they want to set their own goals, pursue their own objectives, and do work the way they want.

If your top sales staff members feel they don't have enough autonomy, they're going to be more susceptible to head hunting and voluntary departure.

Here's how you can combat that.

·       Encourage more independent decision making. Give your sales reps more freedom and opportunities to make their own decisions. These don't have to be huge, company-wide decisions; even small decisions, when made independently, can make a person feel more autonomous.

·       Allow time for personal side projects. Google once famously allowed employees to dedicate 20 percent of their time, or about 1 day a week, to work on personal side projects of their choice. It didn't slow down productivity by much, yet it gave employees a strong sense of autonomy. It also resulted in the birth of many new innovations, which continue to make google a lot of money to this day. Consider giving your sales reps more time and flexibility to work on things that they think are important.

·       Loosen up mandatory requirements. You can also cut back on anything that's mandatorily required. As an example, daily sales huddle meetings can be productive, but top performers can also feel like they're stale or a waste of time. Make them optional for anyone exceeding a certain performance threshold. Generally allow your employees to work however they want to, as long as they continue exceeding performance expectations.

·       Give your best salespeople leadership roles. Consider giving leadership responsibilities to some of your best salespeople. Have them train or mentor new sales reps. Have them develop new strategies. Ask them to give talks or seminars. People in leadership positions tend to feel much more autonomous.

The Growth Problem

Most employees want to feel like they're on a consistent growth trajectory. If your job hasn't changed much in 10 years, what reason do you have to stick around?

Some people want growth and progress for their own sake, as these represent interesting changes that keep things from getting too stagnant. Others want growth and progress so they can earn more money and perform better.

Either way, you can solve the growth problem with tactics like the following.

·       Pay for training and education. As long as you have the budget for it, consider paying for additional training and education. Even if your sales reps are learning things that aren't immediately and obviously tied to sales, this is a valuable strategy for showing your employees that you're invested in them.

·       Offer cross-departmental collaboration. You can accomplish something similar by allowing more cross training and cross-departmental collaboration. Your sales reps will feel more integrated in your business if they get to witness and work with other departments, and they'll learn and grow as a result.

·       Optimize for flow with appropriate challenges. A flow state is a psychological phenomenon in which a person is deeply immersed in the work they're doing. To achieve this, a person must be sufficiently challenged without being overwhelmed – and they must be genuinely interested in the work they're doing. Work with your sales reps to create conditions that allow them to achieve flow more consistently.

·       Establish clear trajectories for long-term goals. Most of your top performing salespeople will have individual, unique goals of their own. They may want to start their own business someday, rise to the top of your organization, or accomplish something specific within the sales realm. These people are going to be much more committed to your business if you give them a clear, unchanging trajectory for achieving those long-term goals. In other words, if your employees feel like they're taking consistent steps toward their long-term vision, they're much more likely to stick with you.

The Problem Ambiguity Problem

The final problem is potentially the most important: it's the “problem ambiguity” problem.

If you don't know what kind of problems your top performing salespeople are facing, or worse, if you don't even know that problems exist, you won't be able to solve those problems effectively.

That's why your first course of action should be working aggressively to determine which problems, if any, are affecting your best salespeople.

What tips and tricks do we have to help you with this?

None. There are no shortcuts. You have to figure this out. Ask lots of questions. Make lots of observations. Get to know your salespeople, inside and out. Do this, and it's only a matter of time before you figure out what the problems are.

Overlapping Strategies for Retaining Your Sales Superstars

We've covered many individual tactics that can help you resolve different problems affecting your sales superstars, but these strategies are some of the best for preventing and solving multiple problems simultaneously:

·       Conduct stay interviews. Most companies regularly practice exit interviews. This is an opportunity for employees to reflect on their experience and share their honest opinions about the environment and conditions in which they work. These can be valuable, but they aren't going to help you retain salespeople, since they've already decided to leave. Instead, conduct stay interviews, picking the brains of your best salespeople to discover their true sentiments before they're even tempted to leave.

·       Get to know your reps individually. Similarly, it's important to get to know your reps individually. Even among the top performers, you'll find a shocking amount of diversity in terms of strengths, weaknesses, perspectives, and values. Different sales reps are motivated to stay for different reasons, so you'll need to discover the right ways to appeal to each employee.

·       Allow autonomy and flexibility. Autonomy and flexibility make your salespeople feel empowered, independent, valued, trusted, and rewarded for their work simultaneously. And as top performers, they've certainly earned them.

·       Offer rewards commensurate with contributions. Finally, make sure you're rewarding your top sales representatives at a level commensurate with their contributions. Depending on the nature of your organization, this may or may not be an easy equation to calculate. Sure, you can probably afford to pay your sales rep a bit less than they’re actually worth – but what happens when one of your competitors steps in to outbid you?

Your business is built on the backs of your sales reps and marketers.

Your teams are incredible.

But they don’t – and shouldn’t – have to do it all by themselves.

At, we have some of the best marketing minds in the industry – and the resources to support businesses of any size or scale.

If you’re ready to partner up and improve the performance and capabilities of your sales and marketing departments, we’ll be waiting for you.

Get started today.


Timothy Carter

Chief Revenue Officer

Timothy Carter is a digital marketing industry veteran and the Chief Revenue Officer at Marketer. With an illustrious career spanning over two decades in the dynamic realms of SEO and digital marketing, Tim is a driving force behind Marketer's revenue strategies. With a flair for the written word, Tim has graced the pages of renowned publications such as Forbes, Entrepreneur, Marketing Land, Search Engine Journal, and ReadWrite, among others. His insightful contributions to the digital marketing landscape have earned him a reputation as a trusted authority in the field. Beyond his professional pursuits, Tim finds solace in the simple pleasures of life, whether it's mastering the art of disc golf, pounding the pavement on his morning run, or basking in the sun-kissed shores of Hawaii with his beloved wife and family.