Should You Keep Rogue Salespeople On Your Team?

The rogue salesperson is a formidable force when it comes to bringing in revenue. But does their go-it-alone mentality have any place in modern sales teams characterized by teamwork and collaboration? Join Proposify CEO Kyle Racki and Director of Sales Daniel Hebert for part four of a five-part series on sales in SaaS as they discuss if the lone wolf salesperson is an endangered species or whether they still have some value to offer your company.

If you’ve spent a decent amount of time immersed in the world of sales, you’ve most likely crossed paths with the lone wolf salesperson.

These elusive sellers go by many names: the renegade; the cowboy or cowgirl; the rogue; the rebel without a cause. Although, that last moniker isn’t entirely accurate—they do have one cause:

Making lotsa money.

Whatever you wanna call them, the cowboys and cowgirls of the sales world follow a distinct pattern of behaviour:

• They follow their instincts
• They’re not big on sharing or cooperating
• They eschew any established process and go it alone with their own
• They see themselves as top-dog and are difficult to manage

But, they also deliver results.

Sales veterans Matthew Dixon and Brent Adamson popularized the lone wolf salesperson archetype in their standout book, The Challenger Sale.

In the study on which the book is based, they found lone wolves to be comparatively rare among average salespeople, but made up 25% of high-performers in complex sales scenarios.

As such, from a pure numbers & revenue perspective, they can be a valuable asset for founders and sales leaders to keep in their back pocket.

But, is this ability to generate profit justification enough for keeping them around?

I believe the cowboy and cowgirl salespeople have some value to offer a company’s sales strategy. But, this value hinges around two critical aspects:

1. Are they willing to share their process?
2. As a founder, can you allocate their talents appropriately?

Bringing on a rogue rep requires you knowing full well what you’re getting into. This is especially true in the early days of a business where the sales process you’ve been laboring to build is still in its infancy.

The benefits of the lone wolf seller

Rogue salespeople are high performers by nature. Say what you will about their tactics; they excel at closing deals and hitting their numbers.

I mean, if they didn’t, they’d be a straight up liability; one who makes the decision to keep them or let them go pretty straightforward.

Hitting revenue quotas is one upside to consider when determining whether there is space for a lone wolf seller on your sales team.

But before we dig into the benefits, there’s one initial question that acts as gatekeeper for a sales leader deciding the fate of the lone wolf:

Will they share their process?

This is the determining factor when it comes to assessing the utility of a rogue seller.

If they are willing to share their strategies and processes, they can be a real asset. The rest of the sales team can learn from them, and you as the sales leader can integrate what they do that makes them successful into your sales process.

If not, and they keep their cards close, their success won’t be transferable to the rest of the team and their sales won’t be repeatable.

This willingness to play nice is tied in with their attitude toward being coached and accepting feedback, something you also need to figure out early on.

If you can track down a high-performing renegade—they are valuable salespeople and thus in high demand, plus, they are a dying breed; more on that later—these initial qualifiers will go a long way to seeing if you they’ll be a good fit.

If there are no immediate red flags, here are some of the benefits to keeping a lone wolf around:

They bring in revenue

This is the main and most obvious benefit to the cowboy seller: they are valuable to your company.

As a sales leader or founder who has targets to hit, if you have a seller on your team who brings in a sizeable chunk of that target themselves it’s hard to consider them anything but an asset.

On paper, at least.

An independent check on a stale process

If your tenured reps are stuck in a rut and consistently underperforming, bringing in a renegade salesperson to shake up the game plan is an interesting method to see if there are ways to improve an established process.

If you’ve gone nose blind to your process, unleashing a lone wolf seller (who wouldn’t stick to the plan anyway) is a great way to identify where your sales process sucks.

By forging their own path, the lone wolf may end up sniffing out a more efficient methodology, perhaps something unconventional you either haven’t thought of or you think may be too risky to implement if there's no evidence it’s going to work.

If you bring a rogue seller on board and give them a clear target to hit, watch carefully how they go about doing it and see if there is anything in what they do that you can integrate into your process.

When the wolf takes in a cub

Even the hardest of hearts soften a little at the prospect of taking an apprentice under their wing to teach them the ways of the world.

If anything else, the renegade seller is a wealth of knowledge, one that can be invaluable to a junior rep at the start of their career.

Mentorship is where a willingness to share shines through strongest. It’s in this role that a rogue rep can have the most benefit to a sales team and especially its more inexperienced members.

Harnessing the ego

For a founder or a sales leader looking to utilize the cowboy-seller strategy, for it to pay off it often requires harnessing the sizeable ego that usually comes part-and-parcel with a high performer.

In the software engineering community, there are developers who are capable of tackling incredibly difficult challenges that 90% of engineers can’t solve. These bright stars, considered as effective and efficient as 10 of their peers, are known, quite rightly, as 10x developers.

There is a good comparison to be drawn against the cowboy seller: I like to think of them as the 10x salesperson. As you can imagine, there is often a rockstar mentality that goes along with this high-achievement.

Their output may be monumental, but they tend to have an ego to match.

In sales, traditionally a hyper-competitive field, some healthy competition can go a long way in improving a sales team’s performance and morale.

But too much can easily tip the scales in the wrong direction.

It’s up to you as a sales leader to nurture that environment carefully, ensuring the proper incentives and commission structures are in place and making sure everyone feels they are an equal part of the team.

In an over-competitive sales environment, big egos can clash, and reps may consider falling back on nasty selling tricks to gain the upper hand in the revenue race.

If your cowboy seller is bringing down the team you need to think about the long-term costs that come along with allowing this ego to run rampant.

Is a team characterised by high turnover and low morale worth the big numbers one rogue seller is bringing in?

When the lone wolf turns on the pack

The rogue seller may be a force to behold, but there are costs beyond the purely financial to letting a rep with lone wolf tendencies roam free.

The trend over the last few years among companies with an industry-leading sales organization has been irrefutably toward teamwork and collaboration. On top of this, the best sales teams enforce strict sales processes which all reps must stick to.

The lone wolf, who typically abandons the team and follows their own process, is a stark contrast to this trend; the antithesis to a team player. If the foundation of a great sales team is a tight process and a strong team culture, anything that threatens that ultimately threatens the viability of the entire sales organization.

Every team has their MVPs, but the overall success of the team often boils down to how well those individuals play with others. High performers are, of course, welcome additions to the team as they create a Darwinian culture where one salesperson’s achievements help bring out the best in others.

Yet this only works in an environment where competition is healthy and wins are shared among all sales reps. If one rep is allowed to run rampant at the expense of others, they may be getting results as far as revenue goes, but their behaviour is going to bring down the team as a whole.

The structure of your sales team also affects whether a renegade salesperson will fit into your process.

When building a sales organization, deciding whether or not to divide your team into specialized roles is a critical decision. If you’re running with full-cycle rep system, a lone wolf seller who’s used to going it alone and handling a sale at every stage of the funnel may well have some utility.

But, if your team is segmented into specialty roles, the lone wolf seller may not have as much success. No matter how good they may be, it’s unlikely they are as good as a rep whose full time job is dedicated to mastering a certain portion of the sales funnel.

A dying breed?

The general consensus among the top thinkers in the sales world today seems to indicate the lone wolf salesperson is an endangered species.

Companies who are setting the bar for sales best practices put a strong emphasis on teams built on a solid process and a culture of sharing and reciprocity. After all, smart sellers know sales is based on relationships. Whether it’s between prospects or teammates, sociability is critical to success in a dynamic B2B landscape.

Cowboy sellers are necessarily opposed to such ideals. As a clear deviation from the status quo, these rogue salespeople threaten the culture needed to hold a sales team together and disrupt the consistency required to grow and scale your team.

The advent of sales enablement as a dedicated role in a sales organization also contributed to the demise of the lone wolf seller. Sales enablement tools and unprecedented access to data has resulted in sales processes so fine tuned that it leaves little room for winging it.

As the hostile, ultra-competitive, sleazy salesperson of the 20th century are fading into obsolescence in modern business, perhaps the lone wolf dies while the pack survives after all.

Alright, I know GOT is over, but surely you saw that one coming?

Conclusion

At the end of the day, it comes down to culture. Are the cowboys or cowgirls on your sales team toxic to the culture, or are they not?

As a CEO with a board to report to, I need to balance the pros—namely, the revenue these sellers bring in—with the potential downsides, like high turnover and an unpredictable sales process, very carefully.

A board might be happy that you’ve hit your targets for the quarter. But moving forward, with the expectation of 2x, 5x, or 10x-ing that number, how does that unpredictable, loose-cannon seller fit into that plan?

Like most complex problems, the solution lies somewhere in the middle. The shift toward cooperation and friendliness among sales teams has been a welcome one. Yet, as is the norm with these paradigm shifts, there is the tendency to overcorrect.

If a cowboy or cowgirl seller can help keep the competitive edge of your sales team honed, let’s do this rodeo. If the culture becomes toxic as an expense, it’s time to rethink their value.

Keeping the cowboys around might be good for the bottom line, but as soon as they start missing their numbers it’s time to show them the dusty trail.

Have you had an experience with a rogue seller? How did it work out for your sales process? I’d love to know in the comments.