Sales Managers Share the Most Important Lessons They’ve Learned and How They Helped Them Grow

by Janey Zitomer
December 11, 2019

The same qualities that make sales leaders valuable closers can translate to management ability. For starters, you have to know how to listen and what to listen for. Secondly, you have to be able to let go of what doesn’t work. 

For Inside Sales Manager Kathleen Glassett, this meant she stopped taking over calls, rewriting emails and providing quick answers to questions that deserve in-depth consideration.

“I’ve become a better manager by delegating effectively, letting go of certain projects, accounts or tasks, and fostering an environment of creativity and critical thinking,” Glasset said. 

We spoke with Glassett and other Boston sales leaders, who shared the most valuable lessons they've learned along their career paths. 



Don’t Rely on Repeatable Processes 

Streamlining solutions is one thing. Relying too much on repeatable processes is another. This goes for selling to clients as well as for scaling your team. “Sales leaders expect results, and they tend to measure their team primarily by a ‘wins versus losses’ quota,” said Azi Cohen, co-founder of WhiteSource. “After a few years of working in startups, I found that, unfortunately, these measurements don’t apply when selling new technologies.”

“During a company’s formative years, the sales process is far from repeatable,” said Cohen. “Sometimes it takes two or even three years to distill the right formula for a win.” 



Embrace Failure

Kathleen Glassett said that as an inside sales manager at Grubhub, she knows that sometimes “done” is better than “perfect.” 

“I tend to overanalyze and agonize over small details which ultimately leads me second guessing myself,” she said. “Learning to be more impulsive, embrace failure and be comfortable doing both came with a learning curve.” 

Looking back, she would have liked to have taken a zoomed-out approach on a more regular basis. 



Engage With Your Team in a Meaningful Way 

According to LogicManager Customer Advocacy Team Lead Will Powell, mentorship isn’t about leading by example alone. 

“Regardless of workload, it is important to engage with your teammates consistently as you would a potential customer. We have been successful in cultivating a team-first culture at LogicManager by prioritizing professional growth over monthly quotas,” said Powell.

As a mentor, it’s your job to figure out how to specifically guide your direct reports in a way they can’t get from others in the field or even the department. This is all the more important when you’re trying to hit certain numbers or convert specific accounts. 

“It is my responsibility to provide my teammates with all the resources necessary to achieve that development, which will naturally lead to success in their roles,” Powell said.



Reassess the Culture You’re Creating  

SmartBear Director of Sales Tom Salah has always responded best to direct, blunt feedback. But he has learned that not everyone communicates that way, especially in high-pressure situations. 

“I have found that helping the team understand the ‘why’ by supporting the ‘why’ with context both from their personal perspective and the overall business perspective gets the best results,” said Salah. 

Knowing this, he's able to communicate more effectively to both the team and individuals, even (and especially) during more stressful growth periods. Salah's favorite part about management? Helping reps establish sales skills that will set them up for long-term success.  


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