Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on October 22nd, 2020

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Brian Moseley


Brian’s been a leading sales rep, manager, and director at three fast-paced, successful marketing tech startups, HubSpot, DataBox, and most recently joining SEMrush. He’s also the owner of a small sailing franchise called Sail Time Boston. In his free time, he loves playing hockey, he’s a big sailor, and I’ve even actually had a chance to snowboard with him out here in Colorado.

Brian will share with us how discomfort can cause growth in your sales career.

Key Talking Points of the Episode:

  • How Brian got into sales
  • Relationship selling
  • Qualities of a top performer
  • Organization culture
  • Building a personal brand
  • Giving and receiving feedback
  • Brian’s definition of success

Key Milestones of the Episode:

[02:40] How did Brian get into sales?

[05:22] Brian’s experience relationship selling

[12:05] How Brian evolved his goal setting and how it changed his definition of success

[15:52] What qualities has Brian seen standout for top performers?

[23:40] What makes Hub Spot’s organization culture unique?

[26:00] How can you build a personal brand?

[30:08] What changed Brian’s perspective in regards to building relationships?

[33:34] How to give and receive feedback

[37:49] How does Brian bounce back after a lousy quota?

[46:56] What is success to Brian?

[44:21] Does Brian love winning or hate losing more?

[44:31] What are some of the qualities of leaders that Brian has worked with?

Resources Mentioned in the Episode:

The Sales Challenger- Brent Adamson and Matthew Dixon

Sail Time Boston

Key Quotes from the Episode:

“If you consistently and voluntarily put discomfort in your life, there’s involuntary discomfort that will happen to you, and you’re more prepared for bad things.”

“When you realize what you’re doing doesn’t work, you need to be good at breaking up with stuff that’s not serving you.”

“I think it’s worthwhile to spend time trying to make jerks, less of jerks.”

“If someone is being rude to others, they’re probably hurting inside. They probably have some hole missing in them that they’re feeling. Their only way to defend themselves from their pain is to be aggressive, and, and make other people feel small.”

“Humans are naturally good and we want to help people, but we’re complex. We have conflicting desires, and we can be selfish, envious and jealous. We can also be kind and courteous and helpful.”

“You've got to try a bunch of things before you find your tribe. Once you find it, really lean into it and double down on it and try to get to know the people inside that tribe.”

“You should always be adding value before you extract value.”

Connect with Brian Moseley:





About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.