Can a selling sales manager be successful? Should sales managers be responsible for meeting their own individual quota? Or is the “Selling Sales Manager” function flawed?

This is a question that frequently comes up for debate. Managing a sales team is perhaps the toughest gig in sales. Sales teams in almost every company are very competitive, having a sales manager that sells can create a very negative working environment since the manager and the team will be competing for leads.

I was recently on The Lunch Break Podcast hosted by James Bawden and we discussed just that. I recommend everyone to listen to James’s podcast it if you haven’t already!

A bit of Background first

When I started working in sales as an SDR 7 years ago. My manager at that time carried an individual quota and we were a small team of 3 salespeople. We did quite well (revenue wise), never competed for leads. We all were responsible for different territories and a different channel of leads.

Throughout my career, I’ve been a selling manager. I can’t even imagine not selling and managing, aren’t we supposed to lead by example? How can you command the respect of your team, if you don’t know where they are coming from?

Some of the best VPs and Head of sales that I know have a personal quota. They keep their skills sharp and refined because they are on the phones closing prospects and clients every day.

Because of this, they have a real understanding of what it takes to get the job done. They are in the best position to teach this to others.

By now, you probably get which side of the debate I’m on :). However, I will go ahead and dissect this question and look at the pros and cons of being a selling manager.

Let’s start off with the cons

Competition between the manager and the sales team

A healthy level of competition in a sales team is great, it increases productivity and brings the best out in everyone. If however, you’re competing with your manager for leads?. Well, all of a sudden it’s a whole new ball game since the sales team directly reports to their manager and a manager’s job is to support them and mentor them. This dual function can be harmful to that relationship.

The team can think that the manager is keeping the “best” leads for his or herself. It’s extremely important that the leads are distributed fairly and there is a well-defined process. Without a process in place, this scenario is a disaster waiting to happen.

Overall, having a selling manager can lead to having a toxic sales culture, alienating the team, distrust and poor morale.

Torn between two roles

It’s tough to be a manager and carry a quota at the same time. This means twice as much work and the sales manager might not be able to prioritize between leading and managing the sales team vs closing deals. 

A sales manager first and foremost job is to manage their team and make sure they bring the best out in them. If the manager is busy closing deals since they too carry a quota, chances are they will neglect their duties as a manager. That can hurt a company’s bottom line. Add two or three more reps to manage in the mix and the selling sales manager function quickly becomes flawed.

Aside from all of the trust and competition issues, these roles are too different and require a separate set of skills to be effective. Either the sales or management will end up suffering.

People need full commitment and clear steps on a single ladder to climb on successfully. If a company wants a manager then they should hire one. If they want a quota-driven sales rep, then they should hire for just that role.

Lack of time

Sales Manager’s time, just like any salesperson should be closely guarded. When your attention is shifting between two different goals, it requires you to shift your focus from one thing to another. When you’re multitasking at that level between having meetings with your team and doing demos, sales calls, sending out proposals and closing deals. Chances are things are going to take longer to get done and the quality of the job done might not be great. 

How do you decide what to prioritize and what to focus on at any given hour?. Well, that can take years and years of practice. Even then can take a toll on how a sales manager manages all these tasks. 

Sales are unforgiving, if you don’t follow-up with prospects on time,  it’s going take longer to close the deals or worse they’re just going to move on to your competitors due to lack of attention. It’s imperative that a manager manages their time immaculately well but that’s easier said than done.

Compensation confusion 

Now anybody who knows salespeople, know that commissions are a serious matter for them. As it should be, since they are the ones that are closing the deals and require gratification (or a pat on that back in form of $$$).

Compensation for salespeople alone is almost always controversial. If you have a manager who both sells and manages a sales team, that makes having a compensation structure that works well, a nightmare. 

Who gets compensated for what?. Does the manager get a commission for closing the deals and gets a chunk off of what team closes too?. If that is the case, who’s to say that the manager won’t keep the best leads for him/herself. The worst part is that even if they don’t, all it takes is the sales team to doubt their manager and its game over. 

It’s never a good idea to pit the sales manager against his or her sales team. And the worst way of doing it is with money.

Having a transparent compensation structure can be a very difficult thing to achieve. With a manager who sells in the mix can turn this into a huge headache.

On the flip side

The problem with some sales managers is that they are not expected to get on the phone and sell. How can they teach and coach something they aren’t doing themselves (or worse, that they can’t do)?.

Being involved in the daily activities is great but a manager must sell in order to experience what his team is going through and most importantly not lose the ability to sell.

They need to have a better understanding of what it takes to get the job done. Ultimately ensuring they are in the best position to teach this to others.

And that’s a nice segue into some of the pros of being a selling sales manager.

Leading by example

It is very easy to relate to your team if you know what they’re going through. A manager that is down in the trenches with their team commands their respect and understands first-hand pain points they are facing. They can easily jump in anytime when a sales rep needs help since they are involved in the selling process.

This not only teaches the sales rep how to handle selling situations, but it often saves a sale as well. This is what the sales manager must be able to do, and it is a crucial part of their job.

Selling as a manager also gives you street cred and your team trust you. Since whatever feedback you will give them won’t be theoretical. It also shows that the manager is taking the effort to learn the pain their team goes through on a daily basis.

Salespeople follow a leader who “knows” what they are experiencing, closes deals alongside them and know the pains associated with it. They work harder for him, follow him through thick and thin since they know he’s been there and done that and continues to do so.

Instant feedback

Managers often get feedback at the end of the week or in one-on-one meetings from their team. Quite often a lot gets left out by the salespeople. One of the benefits of being a selling manager is that you’re able to feedback from the prospects instantaneously. Your sales team does not have to be a proxy between you and the prospects. It also helps to know in real-time if a sales process is working out or not. 

This saves a lot of time and removes the need to wait to get feedback since you’ll have first-hand knowledge of how things are doing. It doesn’t just stop there. As a selling sales manager, you’re better equipped to get feedback regarding the product. Which you can then use and relay it to the product/dev team and help them create the product roadmap that better fits your customer’s needs.

Keeping you on your toes

If you want to get better at something, you must practice regularly. Otherwise, that skill set that you possess, atrophies. If you stop selling as a manager, there is a very high chance your selling skills will depreciate over time. This is very true for salespeople that go on to become managers early on in their careers. 

Selling is your number one asset! You should do everything in your power to make sure you keep “beating on your craft”.

Talent you have naturally. Skill is only developed by hours and hours and hours of beating on your craft.

Will Smith

Managerial roles often require a lot of preaching. Helping team members grow and setting targets for them is part and parcel of the job. However, this isolates managers from practicing what they’re preaching. That kind of disconnect early on in their careers can be very devastating. As it will take them a while to get back on their feet should they want to back to selling again, execution can and will become a lot difficult without staying in touch with selling.

A better salesperson and a manager

One of the hardest things I ever had to as a manager was to get feedback from my team regarding my performance and how I sell. When you’re working with your sales team and selling alongside them. It helps to remove the barrier of communication between you and the team.   

Since you’ll spend time selling with your team especially the new team members after a demo or a sales call you can ask for their observations and critique. Let them know that you may do something incorrectly. Or better yet, do something that does not work on purpose to test them.

This solves the issue of them not wanting to critique their boss. It can help you learn something new that can improve your skill set and you can pass on to the rest of the team. 

This breeds an environment and a team that respects your leadership because you are willing to go in the field and afraid to be critiqued.

Conclusion

Being a “selling sales manager” is not an easy feat. In my experience, some managers have done an exceptional job being one and I’ve seen it fail in a lot of situations too. Where managers were torn between two roles and they did neither well. It requires a lot of trust between the manager and the team.

For selling managers to be successful, one of the biggest factors is the compensation structure for the role. Another point is, well money. Small companies (<$2-$3 Mil ARR) sometimes need a selling sales manager. Due to the high cost of sales management, it very well is a necessity for them since they might not be able to justify the cost of adding a full-time VP/Head of sales (although sometimes that is exactly what is required).

The selling manager does become flawed when you go above managing a certain number of people (4-5 people). At that point, the sales manager’s only goal should make sure their team is doing well.

No matter what, a sales manager should come in, prospect, run demos, close a few deals to “get their hands dirty” and continue to do so.  You can’t build a process without understanding what’s going well and what can be improved upon. 

After that, I think it depends on what stage the company is at. IMO hyperscaling companies need more of the people, process, performance VS. earlier stage where every deal is a learning experience and needs to be more hands-on from the beginning.

Hope this helps shed some light on this topic. Stay tuned for more. Happy selling!