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Sales, Sales Development

How to Be a Better Sales Leader in a SaaS Business

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


Let’s say you’re doing a great job in sales as an individual contributor… You’re crushing your numbers, year on year.

The time eventually comes when someone taps you on the shoulder and offers a promotion.

“We want you to manage a team now.”

Initially the feeling is great. You are eager to take on more responsibility, an increase in your base salary, and the opportunity to lead and get the most out of other people. After all, it’s your pathway up the corporate ladder.

But when you start the first day of the new role, you quickly realize that the skills that enabled you to be a great salesperson, are totally different to what’s required for you to be a sales leader.

As a salesperson you can be incredibly selfish. You’re focused on you, and your numbers alone. Because if you hit those numbers you’re on the path to accolades and financial security.

But as a sales leader your focus needs to turn towards your team, it’s not just about you anymore. This means you need to start putting a much bigger focus on what makes other people successful.

Whether you would like to admit it or not, there’s a skill gap between where you came from and how you plan on being effective in this new leadership role.

So what does it actually take to be an effective sales leader?

Let’s take a look at six things you can do to make it happen.

1. Understand both personal and professional goals

When you start managing salespeople there are really two goal elements you are trying to understand: there’s the professional side of things, and then there’s the individual themselves – the person.

The most important thing to remember is that ultimately you are dealing with a human. So you really need to understand what makes each individual tick. What makes them get out of bed every day and continue to persist in their sales career?

A great salesperson is running at brick walls each and every day, time and time again to be able to succeed. Why would they want to do that? Is it to provide for their family? Are they chasing the accolades? Or do they just want to be driving the fastest car?

Once you figure that out, you can start to really understand what makes them tick and start aligning what motivates them with the outcomes you need to hit your numbers.

The beauty of sales these days is that the skill set required opens up a whole bunch of different career avenues someone can take. Having a clear understanding of what that is at the start of your relationships, will help form a solid foundation of trust, and enable you to get the most out of your reps.

If there isn’t an alignment between the individual aspirations and company objectives then it is going to be difficult to achieve a mutually beneficial outcome.

You want to be consistently checking in with your team members, one-on-one, to see where they are at with their goals. Schedule in monthly meetings and ask them how things are progressing, both personally and professionally, and where you can help.

In the end it’s an individual that is going to be out there trying to get your sales numbers and targets. So you need to work with them, supporting, coaching and motivating them to work hard and grind through the effort to achieve those business results.

Some people, they’ll just do it. They’ve got an intrinsic drive that enables them to push through barriers and be successful. But a lot of others need help and support. Understanding what their goals and objectives are from a personal and professional point of view, enables you to better help them along that path.

2. Know the business metrics

A big part of sales is understanding the impact that you are going to have on the business, and how you can go about influencing that.

To perform to their potential, each individual needs to understand the results that are expected, what that means for the business, and then how they can impact that.

As a sales manager you are looking at the business objectives and the preceding activities that can contribute to these objectives. You are then mapping out the daily activity of your team in a way that inevitably leads to reaching the pre-set goals.

Then each individual within your team has visibility over the important cog they play in contributing to the greater business results.

There’s a great book I’d recommend reading about cracking the sales management code, it’s written by Jason Jordan, and talks all about measuring and managing sales performance in relation to overall business objectives.

cracking the sales management code

3. Get close to your team’s individual metrics

Once you know how your team can contribute to the overall business metrics, it’s your job as the sales leader to effectively tie each individual’s efforts as closely as you can to that end outcome.

You are trying to tap into what is going to make each salesperson successful, and create the sales math that is required to enable them to hit their goals. It’s about identifying what the leading activities are going to be that will help them achieve these goals.

How many phone calls, how many emails, how many meetings, how many demonstrations, how many proposals do they need to meet that goal?

The maths is going to be different for some reps. For example, some salespeople might not like to spend a lot of time on the phone, instead they would prefer to focus on a narrow target group of companies. So you need to tailor this to the individual and understand what motivates each of them.

There also needs to be some physical way to track all of this information. You could use an OKR tool, like 7Geese, 15five or even just a spreadsheet. Sure it can be a little bit of manual work, inputting the data every month, but it will help you hold people accountable.

cheat sheet

4. Use data to identify coaching opportunities

Once you’ve got close to each individual in your team and really understand those metrics, you’ve then got to utilise this data to identify coaching opportunities.

In the past, coaching opportunities were done basically by a gut feeling of the sales manager. They would hear a sales conversation happening on the other side of the room, or they’d see an email that’d been sent. But they were essentially basing their feedback on small pieces of information that may not be a good reflection of the full story.

This kind of information is all hearsay. There’s no data, and no empirical evidence to say: “Hey, this is the correct path for you to take”. So it’s easy for a sales rep to take this feedback with a grain of salt.

By utilising the data, you can break down the activities an individual salesperson takes into three core measurements. For example, how many emails have been sent? (Activity) How many emails were opened or engaged with? (Quality) And then, how many of those emails were responded to? (Conversion)

You can use this data to identify where your sales funnel is “broken”, or where the leads are dropping off.

where your sales funnel is broken

Using data points such as this when you are providing feedback to a sales rep makes the story much more objective. It gives them concrete things they can go and work on, and it also allows them to see progress against the same data. It’s not hearsay anymore.

Using data to identify coaching opportunities takes the “human” element out of it.

Using data to identify coaching opportunities takes the “human” element out of it. If both you and your sales rep have agreed on a set of goals, and agreed that a certain level of activity will add up to achieve those goals, then if the activity isn’t being done effectively it provides a coaching opportunity.

5. Don’t be an asshole

This tends to happen a lot when someone comes out of that individual contributor role and they’re moved into a leadership position. Instead of looking for ways to lead and empower others, they’re too busy walking around trying to demonstrate how much they know. They are using their new position up the hierarchy to wield power over other people and stroke their ego.

To be an effective sales leader you can’t be an asshole.

So to be an effective sales leader you can’t be an asshole. You’ve got to remember that when these coaching opportunities present themselves, it’s not about you. You’re coaching an individual, a person, that is contributing to the greater goals of the business, and indirectly contributing to your success as a leader. The only way to make that happen is to help them succeed too. No one likes being told that they stuffed something up or that their performance is bad.

When you are trying to provide criticism to someone in your team, lead with positives. Tell them about something they did well throughout the engagement, but then also help them understand what they could be doing better. Give them some clear examples of the behaviour that was incongruent to their goals, and then teach them how they can improve on that. Finally, finish off with some good news. The old-school shit sandwich.

You’ve also got to be mindful that you are not giving too many pieces of feedback in one go. People can only take in a maximum of one or two things at a time. So even if you identify lots of different coaching opportunities, just pick one. The one that is going to have the maximum impact and add the most value.

6. Paint a path for future development

This part is about tying everything together from goal-setting to coaching.

You’ve identified what your team members want to achieve both personally and professionally. Then you’ve analysed the business and individual metrics that will help you track and measure the progression of these goals, which has given you sales math. And you’ve started to identify coaching opportunities to help each individual more effectively hit these numbers. There’s lots of employee development avenues in here.

But one other thing you really need to do in order to tie this all together, is to sit down with each individual rep in a one-on-one meeting and paint a path for future improvement and development. The coaching is just one part of a broader picture that links back to their personal and professional goals.

You are using their goals, the data, and the coaching opportunities to shape a path that takes them towards mastery, rather than just picking up some disparate skill sets that may or may not help them in the future.


Effective leadership is about building trust with the people on your team.

That all starts by treating them as humans, and prioritising their goals. They need to know that you care, and genuinely want to help them succeed. That means never missing a one-on-one, allocating specific times to coach them as individuals, and as a group. Whenever you have actions that come out of your one-on-ones, make sure that you do them. Follow up, and follow up regularly, so that there is a culture of gettings things done.

Even take your leadership beyond the one-on-one relationship. Have their back in conversations with other parts of the business, such as marketing or the executives. Go into battle for your team.

All of these little things create a culture of trust and accountability that makes all of the other conversations you are going to have much easier.

The empathy that enabled you to succeed as a salesperson, now needs to turn towards your team. It’s about enabling their individual success and goal achievement, rather than that of a customer.

Have you made the transition from sales to leadership? What did you do to bridge the skill gap?