Accelerate Podcast with Andy Paul
September 1, 2017

#558. A Millennial Sales Rep Joins Us to Talk about Selling. With Bridget Gleason.

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


[2:15] Bridget — who feels fantastic today, and just had a great family reunion — is joined by special guest Josh Phillips, head of the account management team at in Tel Aviv. Josh is on the customer front line for technical help and other needs. [7:06] There are a lot of people skills in sales, and a lot of sales aspects in nearly every job. Josh says his generation is used to short-term targets and goals. Sales speaks to his generation.

[8:23]  Josh is from Manchester, United Kingdom. Andy and Josh bond over the Red Devils and the Romelu Lukaku transfer. Being a striker in football is just like being a sales guy. You’re the pointy end of the stick, and you need to be consistent.

[9:47] Josh says the stereotype of Millennial entitlement is real, for a specific reason. He talks about the educational process of constant targets to hit, for which you get Pavlovian rewards.

[13:58] Josh tells tips he learned getting his Master’s: If you only do as you’re told, you’ll excel; but that doesn’t work in the office. Millennials are surprised to be micromanaged; their supervisors are surprised Millennials want to be unsupervised.

[15:56] Andy says Boomers and Gen Xers misinterpret Millennials. Millennials want to know why things have to be ‘this way.’ That is motivated curiosity, not entitlement. They believe more in a meritocracy.

[18:01] Bridget agrees with the concept of meritocracy, and contrasts that with the Boomer mentality of ‘doing the time’ for the eventual reward. Millennial impatience is a good thing.

[19:45] Josh says technology increases transparency for a workplace of meritocracy. CRM lets everyone see everyone else’s work. Andy and Bridget remember the ever-present sales board. There has always been a ranking.

[21:29] Josh knows very few people who have been six years at one company. Andy notes that people not making their numbers were dropped quickly. You qualified to go to training.

[27:22] Josh says, the more tech comes into sales, the more it distracts the process. The customer buys the person, and the benefits they sell, not the product.

[28:58] Buyers think the Millennials are great at tech, but not as good at connecting with people. Josh says knowledge doesn’t close a deal. Bridget taught him not to have ‘happy ears.’ Proper listening is critical to selling.

[31:16] Technology can only replace some aspects of sales. Successful sales reps will be more human. Josh does not see his customers, so he looks into their social profile.

[32:34] Josh uses video on conferences sometimes. If the customer turns on the video feed, so does Josh. Some only want to chat or do email.

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Contact Bridget Gleason.

Bridget is VP of Sales with, in the U.S. office in Boston, and was previously VP of Corporate Sales at SumoLogic. Prior to that her recent experience includes being VP of Sales for Yesware and SVP of Worldwide Sales for Engine Yard. She can be contacted at

LinkedIn: Bridget Gleason

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Whalr’s platform leverages the “Product Qualified Lead” (PQL) methodology to inform you when prospects are ready to talk based on how they use your product. Partner with Whalr’s data science team to build a “white box” behavior model for your specific business. www,

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Everyone Can Sell, by Martin Lwanga

To Sell Is Human: The Surprising Truth About Moving Others,
by Daniel Pink



About Andy

Andy is the host of the top-rated 6-day per week podcast, Accelerate!, the go-to resource for the best sales advice online. He is the author of Amp Up Your Sales: Powerful Strategies That Move Customers To Make Fast, Favorable Decisions. Amp Up Your Sales is on HubSpot's list of the 20 Top Rated Sales Books of All Time. He is also the author of Zero-Time Selling: 10 Essential Steps to Accelerate Every Company’s Sales (which won Top Sales World's award as one of the Top 3 Sales & Marketing books of 2011.)

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