How to Improve Selling, with Bridget Gleason [Episode 757]

Bridget Gleason, Head of Sales and Customer Success at Tidelift, joins for the final episode of the Accelerate! podcast. What!? That’s right. We have some HUGE changes coming to show next week. Tune in today to learn what’s happening.


  • Bridget has been a guest on Accelerate more than 100 times! Andy and Bridget discuss A Mind for Sales, Daily Habits and Practical Strategies for Sales Success, by Mark Hunter. Curiosity is a great fit for sales if you do the work.
  • Bridget wasn’t satisfied in her career until she got into sales. She desired to talk to customers. Andy brings up hard parts of sales. Bridget doesn’t know of a job where every aspect of it is enjoyable. Make your calls first.
  • Bridget refers to Brian Tracy’s Eat that Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time. Do the hard things first to get to the fun stuff.
  • How do we enable sellers to perform to the best of their ability? Andy lists five factors: skills, behaviors, mindsets, mentors, and experience. What skills enable you to perform at a higher level? How did you learn that lesson?
  • Andy considers listening and asking great follow-up questions to be top skills. The right questions help you to understand the buyer’s needs. That provides great value to the buyer.
  • Bridget shares one of the worst sales phone calls ever made to her; it angered her! It takes lots of practice to make good calls. Show reps how to ask questions and get needed answers without using a scripted checklist.
  • Bridget wasn’t allowed to make a sales call before taking weeks of training. Investing in training pays off in making sales reps more effective. If SDRs were paid more, would they stay longer?
  • Bridget describes Tidelift’s team-selling model. Each member is comped on the total sales number, by their experience. The work is more interesting for everyone. Bridget describes the levels of sales roles at Tidelift.
  • Andy would like to see highly-skilled senior prospectors on a career path starting with SDR. Bridget talks about the professional BDRs she saw in Israel at Would it ‘take a movement’ to have those in the U.S.?
  • Andy says you learn to sell from your customers, your peers, your managers, your mentors, and books. Some of Andy’s mentors were CEOs who were his customers. He recalls the video training he received, which he laughs at.
  • Bridget’s training was very valuable. At Wang, the top reps taught the new reps. Andy visited a retail CEO who mentored Andy to sell to him. Cultivate the relationship before asking for the order. We sell human-to-human.
  • Andy has told customers when his product wasn’t the right fit. Years later, he did business with some of them under more appropriate conditions. Bridget says it’s also the right thing to do. Be trustworthy.