Employee Development

Level Up Your Sales Team with Leadership Training

Find out how you can build a motivated and high-performing sales team that's ready to lead.

Thomas Waites

Director of Sales at Together

Published on 

September 7, 2023

Updated on 

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A career path in sales is pretty unique. You can spend your entire career as a successful individual contributor and never manage people. Whereas, in many business functions like Operations, if you don’t move into a leadership role, you’re capped — at least in terms of career progression.

But sales is different. Even without getting into people management, you can have an exceptional career in sales. As you continue to grow into a seasoned salesperson, you work on larger accounts with more complex, high-value deals. In tech, for example, you might start out as a Sales Development (SDR) or Business Development (BDR) Representative and then progress into an SMB Account Executive role, then an Enterprise Account Executive, and can continue climbing. 

The other path that a sales career can take is in management, and that’s a very different path from a career as an IC. In sales leadership, you could become a team lead, then a manager, and then move all the way up to your company’s executive team, with titles like Director, VP of Sales, or Chief Revenue Officer (CRO). 

Oftentimes, the CRO will oversee areas of the business outside of sales but typically CROs come from a sales background. The truth is that it's challenging for non-sales people to manage and truly understand sales.  Sales leaders are often thrust into leadership roles, and usually have to learn on the fly. And the transition from IC to management can be bumpy and the leap is often something that IC salespeople worry about making. Unless they have a mentor, they probably lack a lot of the soft skills that make a great manager. 

We can bridge that gap with a sales leadership training program, and supercharge it with a mentoring program. 

How does leadership training help in sales?

In my experience, sales teams with strong leadership just perform better, but some of the best reasons to train your sales managers is to:

  • Fuel revenue growth – Whether it’s training on new tools or stronger sales enablement, sales leaders across industries point to training as a way to drive continual growth and meet sales goals. (Salesforce)
  • Create a sustainable process – A leadership training program standardizes your coaching practices and ensures strong leadership skills across your sales teams. 
  • Capitalize on the team’s potential – A good leader can easily identify sales reps with high potential and will find ways to continually motivate and incentivize them.

What are the skills of an effective leader?

In terms of hard skills, sales reps don’t need a specific background, but effective sales leaders must first be great salespeople. 

To me, leadership means setting the course of action that people are taking, like instilling sales philosophy and methodologies, leading your team through tough times, and thinking through strategy. 

Then, they also need soft skills, like strong communication, empathy, emotional intelligence, and resilience. These skills will make your leaders more effective and increase your sales team’s success.

Exceptional sales skills

Some people might debate this with me, but I think that it is very important that if you want to be in sales leadership, you're exceptional as a salesperson yourself. And sales is a little bit unique in that sense.

If your salespeople don't think that you are among the best salespeople, you will lose the credibility and support from your team. In fact, I've heard from a lot of sales reps that they end up with a sales leader who has never done sales, and it just doesn't go well. 

A sales leader also has to have a sales mindset because you can’t really empathize and coach a team if you don't actually have those experiences yourself. So I’d argue that they need all the skills of a sales rep and then some. 

Empathy and emotional intelligence

Sales professionals are very people-oriented, and so if you're not people-oriented in the way that you manage them, then that can lead to all sorts of issues. So empathy is really important. 

People go through a lot of highs and lows in sales, and you need to be able to support the team on that. A leader who has been there is better equipped to support a struggling team member. And they also know what it takes to cheerlead and motivate. 

Part of that is the ability to self-reflect so you have a certain level of self-awareness. In sales, you have so many ways that you can improve. If you’ve got the emotional intelligence to understand what motivates you and your team, you can actually motivate them. 

It's not all that dissimilar to sports. It doesn’t matter whether we’re talking about professional or amateur sports, an athlete can always be better. They need a coach to motivate them and lead them. Sales is the same way.

Strong communication

My team works in mass market sales, where we connect with different types of personalities, roles, and organizations in varied industries around the world. Our sales reps have to be able to communicate with people from all walks of life. This means that our sales managers need those skills too so they can coach their teams. 


For me, resiliency is more important than raw sales skills. Even someone with relatively weaker sales skills but a great mindset can still be successful. Meanwhile, the inverse usually isn’t true. 

In sales, you're getting rejected all the time. Even in tech sales, a good conversion rate is like 20%, and exceptional is like 30%. So even if you're exceptional, that still means the majority of the time you're getting a no. 

And it’s only getting more challenging to close deals. Salesforce reports that 70% of sales professionals say sales jobs are tougher now than ever before. Resiliency becomes even more important so people don’t get buried in the nos and create a sort of self-fulfilling prophecy of failure. 

Intrinsic motivation

An internal drive and competitiveness are key to any sales role, but it’s also important at the leadership level. A leader should foster healthy competition among sales reps but more importantly, they should help to light an internal fire of competition for the salesperson to be their absolute best – breaking previous highs and personal bests. That’s how you push a team to succeed in a performance-driven role like sales. 

How to build high-performing sales teams

A lot of sales managers haven’t coached before. They’re (ideally) high-performing sales reps who want to take on a leadership role. You need to go beyond sales training to give your top performers expert skills for leading and motivating their teams

Understand what makes a strong compensation structure

Compensation structures that are overly complex make it hard for sales reps to set goals. If they don’t understand how they get paid, they can’t achieve their goals and they’re going to lose motivation.

Additionally, incentives that aren’t tied to individual performance and action, tend to cause problems between team members. Let’s say your SDRs set demos for Account Executives, and they get paid based on whether that lead converts. Even if the SDR did an exceptional job, once they pass it to the AE, it’s out of their hands. If that AE drops the ball, now you’ve got an internal conflict because your SDR is being comped on something they’re no longer in control of.

Comp structures that are based on team performance instead of individual performance can also lead to conflicts. Let’s say you have somebody who's performing exceptionally well, but the team's nowhere near quota. That hinders compensation for your most successful sales reps — especially when you consider less than 30% of sales professionals think their team will hit quota this year.

A sales leader, particularly at the executive level, has the power to influence these structures. So the sales team needs someone who understands these issues as VP or CRO. 

Develop an effective coaching program

In Salesforce’s latest State of Sales Report, only about 53% of sales leaders said they coach their sales teams. And while sales professionals say the coaching they receive from their manager is useful, only 26% get weekly 1:1 attention. 

So how do you give a team the one-on-one attention they’re looking for?

Well, I have an SDR optimization sync every week. The SDRs bring their ideas for optimizing our conversions. We discuss their ideas, and then we go implement them. It’s just a matter of creating the space for those sorts of conversations so that people can develop outside of just their core sales activities. 

Just this week, one of our SDRs saw that there was a bit of a latency in notifications for new leads. We were able to resolve the lag, and now we’re seeing those notifications faster.

It might look like a standard weekly standup, but really these syncs are part of my coaching strategy and training program that empowers my SDRs to do their best work. 

Boost your mentoring practices

You also need to empower your senior team members to be mentors and leaders on their team. According to Coqual, mentors “reap significant dividends” and have a greater capacity to “get things done.” Their mentees also experience a more satisfying career trajectory. 

Within a leadership training program, mentoring programs are your opportunity to develop salespeople at all levels — all the way up to senior leadership. 

Most often mentorships focus on developing new skills that are outside of a mentee’s current role. But mentoring can encompass a wide swath of guidance and advocacy. A good mentoring program equips your senior team members with the skills to guide a mentee on their career path.

For example, an Account Executive on my team had a large client that she was in the final stages of closing. She was doing a great job, and then her point of contact got fired and the deal was put on hold. She was really upset, but the outcome wasn’t a result of anything she did. In fact, she did everything right. As her mentor, I reminded her, "The result sucks, obviously, but the process that you followed here was really great, and so you want to continue to do that. Sometimes you can do all of the right things in sales and still not close the deal for reasons beyond your control."

Framing is so important, and I think a lot of sales leaders are too fixated on the results. Results in sales are important. However, a strong focus on creating and following a repeatable process is much more important. You can do all of the right things and not close the deal. You can do a lot of wrong things and close the deal. By following a process, success becomes inevitable. Without one, you’re just hoping for results. A pure results-oriented mindset also isn’t actionable. 

Newer AEs benefit from having a mentor as they progress from a BDR or SDR role to an AE role. A mentor can help shift mindsets from focusing on sales quotas to creating a long-term sales strategy. 

Supercharge your sales leadership training with a mentoring program

When sales leaders become mentors they are involved in the development of folks on the team. This creates stronger relationships that help the entire sales team succeed. 

You can take that a step further and develop a full-blown sales network with mentors from a variety of companies. 

At Together, we understand the power of mentorships in sales leadership training. Find out how a platform designed for mentoring programs can help

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