Unlocking Success: How 3 Sales Leaders Leverage Empathy and Experience to Help Team Members Score

These sales coaches understand the challenges account executives face. They’re proving why mentorship is vital in a field that isn’t always easy.

Written by Lucas Dean
Published on Nov. 28, 2023
Unlocking Success: How 3 Sales Leaders Leverage Empathy and Experience to Help Team Members Score
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Some pieces of advice are easy to understand but much harder to follow. When Order.co Director of Sales Nicole Vilanova advised an account executive (AE) to “sit in the silence” following a proposal review, she was aware of the palpable discomfort that often coincides with that seemingly simple task. 

Since then, following a 20% increase in his close rates, the AE has kept a post-it note on his desk scrawled with that bit of advice. 

In sales, the ups are less frequent than the downs, and discomforts are commonplace. One’s ability to tolerate uncertainty, learn from losses and celebrate successes is an undeniably significant predictor of long-term success. 

For sales coaches, simple yet critical pieces of advice can provide a level of assurance — and even end up a team member’s repeated mantra, oft-cited post-it note or something they pass down to their own mentees one day. 

Distilled into its simplest form, the idea is that empathy goes a long way — in sales, leadership and life. 

The complexities of the field are best addressed with a deft, understanding hand and the realization that one’s approach to leadership can shape not only individual success but also the legacy of mentorship for those who follow. 

In this article, conscientious leaders at Order.co, Sensor Tower and Smartly.io offer insights into what it takes to be a better sales coach and how practical guidance can leave a lingering impression. 

 

Nicole Vilanova
Director of Sales • Order.co

Order.co purchasing software helps business administrators and users place orders, control spend and submit payments across their vendors.

 

Describe your role as a sales coach. How did your career journey lead you to that position?

My career began in account management before moving into a new business role for a medium-sized software company. I was fortunate to work under leaders dedicated to their teams’ professional and personal growth. While excelling as an individual contributor (IC), I took on many iterations of leadership and mentorship roles, mostly because I genuinely enjoyed coaching others. Even while leading the team as an IC, I found that my highs were higher when I could coach someone to their win versus getting that win myself.

For a brief stint, I wanted to become a therapist because I loved the idea of coaching individuals to overcome their challenges and supporting them to lead more fulfilling lives. When I made the transition to sales management, I quickly realized that a sales coach is the perfect blend of sales skills and creating a space for people to be vulnerable. 

People get into the sales profession for many different reasons, so it’s important to understand what motivates each individual and help them navigate the highs and lows of the role.

 

What separates a good sales coach from a great one? Are there specific skills all great sales coaches have?

It’s all about compassion and communication. While these skills are necessary to be a great individual sales contributor, they become even more critical when taking on the role of a sales coach. Having the ability to connect with your reps on a personal level to build that trust early on and understand what motivates them is essential. It will allow you to provide personalized guidance and support, not only in closing deals but in handling everything else that comes with the gig. 

Creating a space for open feedback and communication from both sides is necessary to build trust. The ultimate goal is to communicate with specific and sincere praise paired with kind and clear criticism. 

 

The ultimate goal is to communicate with specific and sincere praise paired with kind and clear criticism.”

 

Also, especially in the startup space, being a sales coach means actively participating in the sales process alongside your team. You must be willing to get in the trenches with your people to lead by example, offer real-time feedback and brainstorm challenges together.

 

Describe a time when sales coaching made all the difference in a rep’s performance. What impact did this have on the business?

I clearly remember mentoring an AE who came to us from a company that specialized in smaller, transactional sales that didn’t require strategic negotiations. Although his drive was there and he was strong at building pipelines, he struggled to close deals and often resorted to excessive discounts. We pinpointed the need to improve his demo-to-close rate.

Without experience working enterprise deals, the idea of asking for a high price point made him personally uneasy. To address this, we held weekly sessions to tackle negotiation role plays. We prepared for potential objections, practiced saying the dollar amount aloud and embraced the typical uncomfortable silence that follows a proposal review. We mapped out why we priced it the way we did, and this emphasis on fairness for both parties only boosted the confidence in his pitch. 

Over the next quarter, he increased his close rates by around 20%, ultimately becoming the top performer on the team that year. He called out those negotiation sessions after making it to the President’s Club. We continue to have monthly mentorship meetings, and he still keeps a post-it on his desk that reads “SIT IN THE SILENCE.”

 

 

R. Andrew Sprague
Director of Sales, Financial Institutions • Sensor Tower

Sensor Tower provides market intelligence and analytics for the mobile app economy through its software suite.

 

Describe your role as a sales coach. How did your career journey lead you to that position?

I’m currently in a player and coach role at Sensor Tower. I manage my own book of business alongside a team of AEs and BDRs. As a sales manager, I act as a sounding board for my team. Our AEs and BDRs know their accounts better than anyone else at Sensor Tower. I listen to their thoughts and give feedback on their strategies, but ultimately, I trust my team to do what’s best.

I spent my earlier career in equity research, then hopped to Sensor Tower as an account executive. After a few years of exceeding my individual goals, someone told me that my impact could be exponential if I were to lead a team and help those team members hit their composite goals.

The bigger the team, the bigger the goals. The bigger the goals, the bigger the impact on revenue. I wanted to increase my impact while helping others hit their goals and grow their careers.

I started managing a team shortly after the suggestion was made.

 

What separates a good sales coach from a great one? Are there specific skills all great sales coaches have?

I believe in the mantra, “There’s more than one way to skin a cat.” 

A good sales manager teaches their team how they would do something. A great sales manager listens to how their team would proceed, assesses the strategy’s validity and either supports their team in that strategy or suggests an alternative based on experience.

Team members can exercise ownership, buy in and lean on their unique strengths when their sales manager realizes there’s more than one way.

 

Team members can exercise ownership, buy in and lean on their unique strengths when their sales manager realizes there’s more than one way.”

 

Describe a time when sales coaching made all the difference in a rep’s performance. What impact did this have on the business?

I’d like to toot my own horn here, but I still have much to learn as a sales manager. I’ll thus toot someone else’s. 

When I was an AE, my sales manager, Anthony Bartolocci, once told me, “I’m here if you need me. Otherwise, I’ll get the heck out of the way.” That seemingly benign and playful comment did a lot for me as an AE. It made me realize my success was up to me, but it also reminded me that I had a team supporting me should I ever need it. And trust me, I did. 

With Anthony’s guidance and the latitude he permitted me, we had some pretty big quarters for Sensor Tower. Not only that, but he was able to build a team that owned its success and could, therefore, scale attractively.  

I try to replicate that comment’s underlying ethos with my team today.

 

 

Rob Berzinskas
VP of Enterprise Sales • Smartly

Smartly.io is a SaaS digital advertising platform that helps brands better reach audiences, engage creatives and learn what performs best across the largest media platforms.

 

Describe your role as a sales coach. How did your career journey lead you to that position?

My role today is leading an enterprise sales team at Smartly.io. My role as a sales coach is to focus on several things: ultimately, the team’s performance in hitting targets, but also to help the team in all aspects of their role. 

This ranges from helping and influencing strategic deals, providing feedback on how we can collectively improve and grow, helping to remove internal and external obstacles and being a sounding board to help ideate and find solutions to improve our business. Each day in my role is different, which is what makes it rewarding to be able to take on challenges and ultimately improve our chances of success.

My journey into sales, and inevitably, leadership roles, started with a foundational background in playing sports. I was fortunate enough to play baseball competitively through college, where I learned a lot of the fundamentals of being a good teammate, being a captain, leveraging the team’s collective strength and ultimately developing a love for competition and winning. I was also very fortunate to have some amazing mentors and coaches who trusted me and instilled confidence in my abilities.

 

What separates a good sales coach from a great one? Are there specific skills all great sales coaches have?

I think what separates a good sales coach from a great one is their keen ability to recognize the motivating factors across their team — what makes them tick? For some, it’s purely about compensation, while others care about praise and recognition or seek the opportunity to be promoted and take on more responsibility. 

And for some, it’s perhaps a combination of a few of these things. I think great sales coaches also recognize that while we have a goal to hit, we are humans with lives of our own outside of the workday. Empathy is probably undervalued in the sales world, so I believe great sales coaches can help cope with the ups and downs while keeping a steady hand in the face of tougher markets. 

 

Empathy is undervalued in the sales world; I believe great sales coaches can help cope with the ups and downs while keeping a steady hand.”

 

Lastly, great sales coaches are master communicators who can motivate their teams to new heights. The success of a sales coach is predicated on the success of their collective team. When everyone is bought in on being open to feedback, striving to improve each day, being transparent about their needs and doing what’s best for the team, you have the recipe for sustained growth and success.

 

Describe a time when sales coaching made all the difference in a rep’s performance. What impact did this have on the business?

I’ve found that helping to improve a rep’s performance ultimately comes down to an exercise of priority. There is only so much time in a given day or week to focus on the areas that can drive better performance. When helping a seller who is falling behind, we often need to identify a few key areas and then prioritize accordingly. Things like keeping a laser focus on our ICP, asking the right kinds of discovery questions, hitting the organization at the right levels and so on can all impact improving performance. 

In particular, what I find is that reps spend too much time on deals that ultimately don’t align with our strategy and ICP. The time and effort to close a large deal is often the same as to close a smaller one, so placing your bets on the right kinds of accounts can be the difference in hitting or missing the target. Great sales coaches can do this at scale across their teams, balancing both pipeline growth of the right kinds of accounts while improving overall close rates, and this can create a serious positive impact on the overall business.

 

 

Responses have been edited for length and clarity. Images provided by Shutterstock and listed companies.

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