How to Be a Better Sales Leader

At Zipline and Cisco Meraki, sales professionals aim to lead with accountability and empathy.

Written by Taylor Karg
Published on Jul. 02, 2021
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Generally speaking, sales representatives know that their manager’s leadership style has a direct impact on their individual success. In fact, according to a survey conducted by Harvard Business Review, 69 percent of sales reps who exceeded their annual quota rated their sales manager as being excellent or above average. The survey also found that there’s a direct correlation between the success of the entire sales organization and the quality of its leaders. 

But what exactly makes a leader extraordinary?

According to the following local sales reps, it comes down to the ability to listen with empathy, build positive morale and provide both good and bad feedback. 

 

Image of Irene Scher
Irene Scher
SVP of U.S. Sales & Customer Success • Zipline

According to Zipline’s SVP of U.S. sales and customer success, new sales leaders should always hold their team to a high standard. That way, they’ll be able to tell quickly who is a good fit for the team and who is not.

 

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

Great sales leaders are able to create cultures of accountability and discipline while inspiring their reps to achieve their full potential. 

The best sales leaders motivate their teams through both wins and losses. They know that losses represent some of the most important opportunities for coaching and organizational learnings. They are consistent about celebrating wins, even wins that precede bookings (i.e. a great meeting or qualifying a new deal), because teams pay close attention to what leadership celebrates.

Sales is often learned in an apprenticeship format: leaders and their teams work hand in hand as thought partners throughout a sales motion. The best leaders act as coaches, giving consistent, thoughtful advice for improvement along the way.

Do not expect less of your team than you expect of yourself.”

 

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

I push myself to always search for edge — improvements or changes that can be made to the sales strategy and motion to stay one step ahead of the competition. Sales is a craft that continuously changes. The brilliant cold email heading that resulted in a 20 percent open rate last year doesn’t work this year because everyone is using it. Prospecting platforms such as Outreach and Salesloft are achieving almost universal adoption because they have a sequence of nine to 11 consecutive customer emails that appear personalized but don’t require the rep to lift a finger. As a result, prospects are so inundated with sales emails that using emails for prospecting is much less effective than it used to be. These platforms may be cannibalizing their own market. The bottom line?  You constantly have to evolve in order to stand out and capture your prospect’s mind share. 

When I’m building a sales org, I aim to hire people who can level me and the rest of the team up in some way. Having a team of folks who spike in different skill sets helps keep the whole team iterating and staying ahead. 

 

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

For leaders who have just transitioned from individual contributors into a leadership role, you’ll probably find yourself gravitating toward the activities that made you successful as an IC initially. You might offer to build a slide for your direct report or lead the next intro call with a new prospect. Whenever you have the urge to do this, remember the following: do not expect less of your team than you expect of yourself. Hold your team to the standard you set as an IC. They will either rise to meet you, or if you have someone that’s not a fit, you’ll find that out much sooner.

 

Image of Christy Cook Olcese
Christy Cook Olcese
Director, Cisco Meraki Americas Partner Organization • Cisco Meraki

Christy Cook Olcese is a director at Cisco Meraki, a provider of cloud-managed IT solutions. Her advice to sales pros just starting out in their leadership journeys? Transition your thinking from a self-centered approach to one focused around the team. 

 

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

The most important quality found in a great leader is the ability to listen empathetically. Without actively listening with the intent to understand, leadership quickly becomes a dictatorship and teams become resentful and unmotivated. My goal is to lead teams of happy, fulfilled members who feel supported and heard. Once a leader fully listens and understands, he or she is able to begin to remove obstacles and provide real value.

It’s our job as leaders to take care of our talent.”

 

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

In this age of multiple devices emitting endless alerts from a variety of sources, it’s nearly impossible to be an active listener without being intentional about it. I’m continually working to be purposeful about focusing on the person I’m engaging with by hiding email, silencing my phone, and taking notes using pen and paper to keep myself focused on the discussion at hand. There are inevitably a few follow-up action items to tackle afterward, and I keep to-do lists to ensure I am keeping my word and delivering on my promises.

 

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

The transition from individual contributor to leader can be a tough one. Shift your thinking from a self-centered approach to one focused around the team. Every single decision should center around helping others grow, learn, develop and have the very best time of their career while in your care. It’s our job as leaders to take care of our talent. It’s a competitive industry out there, and attrition is costly. Great leaders make a positive impact on people every day, and build loyalty and trust by putting the team first. Treat the responsibility with the weight it deserves — leadership is a privilege.

Responses have been edited for length and clarity. Images were provided by the featured companies and Shutterstock.