It’s not the wins in our life that showcase our true strength – it’s how we respond when we get knocked down…badly! 

Greg Cummings had just been laid off from a startup after underperforming. He came back to Salesforce, put everything he had into proving he belonged there, and still fell short of where he thought he should be. 

When he looked at his territory for the following year, stripped down and reassigned to industries he had no excitement for, he contemplated a decision that a lot of sellers consider but never talk about.

Should I leave sales entirely? 

Greg spent six years in the Marine Corps before starting his career in medical device sales, walking into operating rooms at four in the morning to tell neurosurgeons what they were doing wrong. 

He transitioned into tech, found his way to Salesforce, and spent years hovering between $100,000-$200,000 W2 income. Good, but not great. Definitely not what he knew he was capable of.

Then came the layoff, the return to Salesforce, another underperforming year, and a moment of real reckoning. 

Was he even cut out for this? Was his early success just luck?

Instead of quitting, Greg made a different decision. He decided to invest in himself and get help by enrolling in Untap Your Sales Potential. 

His first year, he doubled his income to $360K. His second year, working with me 1:1, he made $970K.

But his income growth is not the most interesting part of our conversation.

What’s most interesting is who he had to become in order to reach that level. 

During our interview, Greg talks about how he stopped pitching and became genuinely curious about people’s problems. He talks about only working deals with executive engagement, and what it takes to have the courage to bring executives into deals early on or walk away. 

We also got super personal and Greg discussed the changes he had to make at home to begin truly enjoying his life outside of work. Prior to coaching, Greg was doing all the cooking, yard work, house projects, and felt constantly depleted and drained. 

On our first 1:1 coaching session, the first assignment I had him do was hire somebody to mow his lawn. This first step began the process of outsourcing everything that didn’t bring him joy and robbed his free time, then re-allocating that time to spend with family. 

Here is what we covered on the podcast :

• Going from the Marine Corps to medical sales to Salesforce
• The layoff, the underperforming year, and questioning whether he should leave sales
• Why he finally reached out for help when he admitted he couldn’t succeed on his own
• The inward to outward mindset shift
• How to sell to CEO’s 
• Why executives are much easier to talk to than mid-level buyers
• The playbook Greg now teaches new hires: spend almost no time learning product, spend all your time learning how to talk to executives
• The mindset shift behind outsourcing: what your time is actually worth, and why doing everything yourself is not a badge of honor
• Clearing mental clutter and why Sunday night no longer feels heavy
• Why he moved from sales coaching into therapy, men’s groups, and church involvement
• His message to anyone who is stuck: be humble enough to ask for help, because the journey never stops

Greg’s story is not just about hitting a number most sellers only dream about. It is about what happens after you hit it, and having the courage to keep growing in the parts of your life that success alone will never fix.

Watch the full episode here: https://youtu.be/iaTjMcGE6HE