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Key Traits Shared by Top Sales Performers w/ Bridget Gleason [Episode 607]

Bridget Gleason is VP of Sales for Logz.io and my regular partner on Front Line Fridays.


  • Andy and Bridget discuss going to Dreamforce. Andy was interviewed by Matthew Bellows of Yesware. Dreamforce took over several venues in San Francisco.
  • Bridget is going to Reinvent in Las Vegas. Amazon books all venues and sells them to sponsors.
  • Bridget will go to Boulder to visit a friend’s book club discussing The Lemon Tree. At work, there is always more to do than there is time to do it, as is typical with a startup.
  • Andy has been talking with leaders about who should choose sales strategies and tactics — reps, managers, or executives? Is there too much command and control in sales? Where do the science and art of selling combine?
  • Andy believes we are hurting ourselves by constraining the creativity and individuality of our reps and account executives. It shows itself in industry-wide results. But we have a system that leaders are loath to change.
  • Sales reps follow a script to sell to personas. Frontline managers are like helicopter parents. They do not let reps solve problems. Andy tells how he was given freedom — once he was trained — to adapt his process to hit quota.
  • Bridget attributes Andy’s case to the better training that was given in the past than reps receive today, and to the longer time a rep stayed in a role then, contrasted with reps, today. Reps today look for structure in their role.
  • Bridget and Andy discuss one thing top performers have in common. Bridget says it is self-motivation. Andy says it’s that they all break the rules. They shape the process to what works best for them.
  • Andy says we are not providing an environment to create more top performers. The people who try successful measures are given more rope to explore. He worries that holds back average performers. Are quotas too high?
  • How do you engage the middle group of sellers to elevate their success? Andy gives one idea.
  • Investors put pressure on startups to scale up, but hiring more sales reps dilutes the quality of deals and sales. Is the quota still serving profit interests?
  • CSO Insights says 50% of reps make quota. Another source says we are closing 20% of deals in the pipeline. A fundamental change is needed in sales thinking. Once people taste success, they want to keep succeeding