Tech Sales with Carter

Why More Dials Won’t Fix Your Sales Problem


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In this episode, I sit down with Jordan Benjamin, CEO of My Core OS and former 6x President’s Club member at HubSpot, to talk about the mindset and psychology behind sustainable sales performance. Jordan breaks down the biggest lies reps believe about success, including the idea that more hours and more dials automatically lead to better results, and explains why energy, self-awareness, and emotional resilience are often the real drivers of consistent performance. He also shares how top reps can tell whether missed quota is really a skill problem or a mindset problem, and why confidence, internal stories, and self-belief quietly shape how people show up on calls every day. 

We also get into social selling, career growth, and what reps can do when they feel stuck. Jordan explains how he built My Core OS from corporate workshops into a more direct-to-consumer coaching business, why LinkedIn has become such a powerful channel for both prospecting and brand building, and how sales reps should think about using it more like a landing page than a resume. He also shares practical advice on gratitude, imposter syndrome, asking for help, and how to structure a strong interview story around why you, why now, and why this role. 

TOPICS WE COVER

  •  Why more hours and more dials are often not the real answer to better sales performance 
  •  How to tell whether a rep is missing quota because of skill issues or mindset issues 
  •  Why emotional intelligence, self-awareness, and confidence matter so much in sales 
  •  How Jordan built My Core OS and what changed as he moved from corporate workshops to coaching individuals 
  •  Why LinkedIn is such an overlooked tool for prospecting, personal brand, and social selling 
  •  How to handle imposter syndrome, build better habits, and structure a stronger interview story 

ABOUT THE GUEST

Jordan Benjamin is the CEO of My Core OS, where he helps salespeople, leaders, and teams perform at a high level without burning out. Before that, he spent about 15 years in tech sales and was a 6x President’s Club member at HubSpot. In this episode, he shares lessons from both his sales career and his work coaching sellers on mindset, psychology, and sustainable performance. 

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about My Core OS: https://www.mycoreos.com/

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Tech Sales with CarterBy Carter Armendarez