053 – How to Succeed in Software Sales with Trent Dressel

053 – Trent Dressel is a Senior Account Executive (salesperson) for a software company and runs a YouTube channel (10.5K subscribers as of May 4, 2022) with practical advice for individuals in the software sales industry. Trent has made over 50,000 cold calls, and in his own words “actively tries to have no work life balance.”

Thomas and Trent discuss his path to this industry, the correlation between sales experience and entrepreneurship, the mindset required to have an extraordinary career, how Trent would approach achieving diversity of thought, identity and gender as a corporate leader, and the pros and cons of chasing money and prestige.

2:30 – What is Software Sales, Trent’s path to it, how he got into content creation and his upbringing 
7:00 – How did Trent make the decision to go public with his online persona and make YouTube videos about career advancement?
10:00 – what is the connection between sales and entrepreneurship? 
14:30 – What is Trents philosophy on D&I strategy in a corporate context? 
18:30 – What are the qualities Trent looks for in an organization as a candidate? 
23:00 – Why does self-development matter? 
26:30 – the pros and cons of being driven by status and prestige
32:00 – Gender representation in sales 
35:00 – Men and taking feedback 
40:00 – personal finances 
46:00 – Spark by Seek Discomfort Conversation Games

  • Trent’s Question: What is a misconception that people have about you?
  • Thomas’ Question: if you were to die, would you be satisfied with what you have accomplished? 

Trent’s Top 3 Books:
How to Win Friends and Influence People
Principles – Ray Dalio 
Man’s Search for Meaning 

Trent’s YouTube: https://www.youtube.com/c/TrentDressel
Follow Bro Nouveau on Instagram: https://www.instagram.com/bronouveaupod/