How to Be a Better Sales Leader

Mentorship, setting a vision, showing vs. telling — here are a few of the strategies three Boston sales leaders have found most effective in the workplace.
Written by Colin Hanner
July 8, 2021Updated: July 8, 2021

Here’s a sobering thought: If you were to gather four salespeople in your organization for a meeting today, industry statistics show that at least one of those people won’t be with your organization this time next year.

If you work in sales, however, this may not surprise you. After all, the fast-paced, competitive nature of the business isn’t for everyone, and the turnover rate in the industry is estimated to be as high as 27 percent, double the rate of the overall labor force. Couple that with the fact that $15 billion is spent annually on sales training and an additional $800 billion is spent on incentivizing salespeople to stay with their organization, and attrition could easily be one of the most costly factors for a high-functioning team. 

So how can organizations avoid such a pitfall and keep team members motivated? Sales leaders may have the answer. 

Managers across sales organizations are responsible for their teams from top to bottom, from knowing the strengths and weaknesses of their contributors to guiding them to a larger target goal. No matter the size or scope of a company, it’s not a straightforward or easy role.  

“This is sometimes really challenging to navigate as a leader because you’re not just dealing with the ups and downs within your own role but also within those roles that report to you on the team,” Teikametrics’ Manager of Strategic Growth Allie Kendall said. 

But if leaders are failing to take on the challenge and constantly improve the functions of their team, that can have serious ramifications for the larger group. According to Gallup, 50 percent of employees who leave their jobs do so because of their manager. 

“As a sales leader, you have to build trust with your team so you stand a chance,” Jobcase Head of Sales Benjamin Kuntz said. 

So how can you become a better sales leader? Below, Kendall, Kuntz and Forward Financing Sales Manager Evan Comeau explain how they’ve become sales leaders at their organizations, how they’ve improved their leadership skills, and what advice they would give to emerging and established leaders alike. 

 

Evan Comeau
Sales Manager // Forward Financing

Show, don’t tell. For Evan Comeau, a sales manager at Forward Financing, leading by example is one of the defining traits of a sales leader, as it can “show your team how you can handle certain situations instead of telling them what to do.”

 

What are the key skills or characteristics of a great sales leader, and why?

I believe every sales leader needs to be dependable, empowering, and inspiring. First, every sales rep needs a leader who they know will give them their undivided attention when called upon to coach, lead or give out general professional advice. Also, allowing your reps to perform tasks that are outside, or even above, their typical day-to-day responsibilities is a great way to make them feel like they are making a significant contribution to the company. And finally, no matter how good they may be, every sales rep is going to hit a rut at some point. It could be poor performance, burnout or just not being satisfied with the position. A good sales leader listens to whatever the issue may be and then makes it their mission to turn the ship around. Treating each case of dissatisfaction with the careful attention it deserves is vital for a consistently high-performing sales team.

What have you done to strengthen or improve these characteristics in yourself? 

I’m dependable in that I have regularly scheduled one-on-one meetings that are structured in a way to promote improvement, constructive feedback and guidance. I empower others by bringing more junior reps with me into interviews, which can be fun and helps them gain valuable experience. I’ve also been taking small projects off of my plate and giving them to my reps. And lastly, I inspire by having sporadic competitions or spiffs with a reward that has helped keep burnout to a minimum.
 

While it may feel time-consuming now, it is important to show your team how you can handle certain situations instead of telling them what to do.”


What’s the number one piece of advice you would share with sales professionals who are just starting out in their leadership journey?

The biggest obstacle I overcame when transitioning from a senior sales role into a leadership role was being more of a “shower” instead of a “teller.” While it may feel time-consuming now, it is important to show your team how you can handle certain situations instead of telling them what to do. Whenever they come across similar situations in the future, they can handle them themselves. For example, when a rep comes to you to ask how you would handle a pitch, instead of telling them exactly what to say, you should instead ask them how they were planning on pitching it first and then guide them in the right direction.

 

Allie Kendall
Manager of Strategic Growth // Teikametrics

Teikametrics aims to help sellers and brand owners optimize their e-commerce businesses on Amazon and Walmart.com. For Allie Kendall, the manager of strategic growth at the company, finding mentors and resources to help fuel a growth mindset has helped her become the sales leader she is today. 

 

What are the key skills or characteristics of a great sales leader, and why?

I think one of the most important things is getting to know your team, what their strengths are, and then ensuring that you are playing to their strengths. So for example, if you have someone who's really good at cold calling or really excels at email communication, identify that as a strength of theirs and reinforce it. I clearly call attention to it and reward that strength, and also ensure that they’re utilizing that strength to the best of their ability by bringing it to light across the team to encourage further collaboration. 

 

What have you done to strengthen or improve these characteristics in yourself?

I’m a really firm believer in finding mentors and utilizing all of the knowledge they can provide. Whether it’s somebody from a current job or an old job, it's important to find someone whom you can turn to for tips and tricks and someone you can always continue learning from. I think that’s really crucial because no leader is truly an expert in every subject. There is always more that we can do as managers to continue learning. 

A growth mindset is something we often help propel at Teikametrics, so this really resonates with me. We can pull, learn and grow from external resources. For example, I took the Dale Carnegie Course, which was a huge pivot in my sales career. I then went on to become an assistant for the course, so I basically got to go through the class again from a completely different perspective. I also often reference the book, “Never Split the Difference” by ex-FBI hostage negotiator Chris Voss. I mention it probably every day to the point where the sales team laughs when I bring it up because I talk about it so much, but I really believe that looking internally at your own career, you can find mentors anywhere who can help make you a better leader overall.

There is always more that we can do as managers to continue learning.”


What’s the number one piece of advice you would share with sales professionals who are just starting out in their leadership journey?

Sales, just by the nature of the role, has a ton of ups and downs. This is sometimes really challenging to navigate as a leader because you’re not just dealing with the ups and downs within your own role but also within those roles that report to you on the team. I think the biggest thing I come back to in those moments is actually a piece of advice Anderson Cooper offered when he came to speak to my university. It was simple: “Out-hustle everybody else around you.” I think about that all the time: It’s not about the ups and downs; it’s about consistently out-hustling, showing up and doing your best every single day, for ourselves and for the team.

 

Benjamin Kuntz
Head of Sales // Jobcase, Inc.

Jobcase is a social media platform dedicated to empowering and advocating for the world’s workers. Through a combination of vision, focus, accountability, self-awareness, empathy and gratitude, Benjamin Kuntz, the head of sales at the company, said that sales leaders can set the tone for an efficient team. 

 

What are the key skills or characteristics of a great sales leader, and why?

Great sales leaders embody a combination of vision, focus, accountability, self-awareness, empathy and gratitude. First, setting a vision is critical. Sales teams want to know the why. So translating where you’re going into a plan of action keeps everyone rowing in the same direction. Second, if everything is a focus by definition, nothing is. Sales teams excel when attacking specific targets. Leaders can ensure focus by zooming in on the right opportunities and removing obstacles. Accountability makes growing revenue a lot easier. Salespeople know the job — whether they’re winning or not — but clarity about expectations and performance helps them create consistent inputs, forecast outputs and exceed quotas. Also, sales leaders need to be self-aware about their strengths and weaknesses. It’s important to recognize when you need others to be strong in areas you are not. In this post-pandemic world, empathy wins. Building strong trust with your team and genuine client relationships will absolutely drive business growth. Lastly, in a culture of accountability, gratitude is vital. Usually, large deals get the credit, but it’s important to recognize the little things that got you there.

What have you done to strengthen or improve these characteristics in yourself? 

A big part of establishing a vision is about spending time with executive leadership at Jobcase. Our interactions help me understand the direction the company is taking and allow us to share insight for revenue opportunities. Studying data or competitive intel helps me adjust our focus or objectives if necessary. 

I hold weekly one-on-one meetings with team members and address areas for improvement through performance reviews. But accountability is also about reviewing our systems. Digging into the status of pipelines and accounts can determine how best to reach or serve potential customers. 

I schedule time to be self-aware, often evaluating my own conversations and decisions. I also welcome 360-degree feedback, knowing that my team can make me better and expose any barriers they’re facing. It pays to keep learning, and I try to read a leadership book every quarter. 

In general, over the last year, we all have had some poignant moments. This new normal is teaching me to look for opportunities to praise good work and recognize people. It’s also shown me that empathy is at the heart of helping Jobcase’s members and clients succeed.
 

Sales leadership isn’t a job title or role within an organization. It’s all about taking action and leading by example.”


What’s the number one piece of advice you would share with sales professionals who are just starting out in their leadership journey?

I actually have three critical pieces of advice: First, when you are just starting out in your leadership journey, make sure you have the right team in place. It’s all about the people. You can have the most sound sales strategy in the world but, with the wrong people, you will never optimize the opportunity. In fact, if you have a strong team you won’t necessarily need the perfect strategy. The right people will figure it out and pull it through. 

Second: Trust is vital in sales leadership. If your team trusts you, they will tell you the truth. And when you get the truth, you can act quickly. As a sales leader, you have to build trust with your team so you stand a chance.

Finally, sales leadership isn’t a job title or role within an organization. It’s all about taking action and leading by example.

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