Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on January 13th, 2022

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Love The Game, Not Just The Outcome w/ Jake Dunlap


Jake Dunlap, CEO of Skaled Consulting joins us on this weeks episode.

As a veteran sales leader and executive of many years, Jake has several nuggets of wisdom to share in many areas, such as coaching, multitasking, burnout, headcount management and more.

Jake talks about chasing growth instead of wealth, always looking for ways to develop one’s skills, and loving the sales game, not just the outcomes. Jake’s approach to problems is that of one who truly loves sales and problem solving. Everyday is a chance to learn. Everyday is a chance to get better. Everyday is a chance to try new shit, break new things and try something different.

Episode Notes


  • Sales is a process
  • Invest in training and onboarding early
  • Consistency and empathy: Building trust as a sales leader 
  • Humans suck at multitasking 
  • Coaching should not breed dependency
  • Headcount should not determine the worth of a sales leader
  • You don't feel burnout if you truly enjoy doing something
  • You have to own your career development
  • All your problems have already been solved before 
  • Chase growth and wealth will follow later 
  • The trick to dealing with discomfort
  • Love the game, not just the outcomes


Jake: "Sales is a process. It is just as much science, if not more science than art. There are right and wrong ways to move customers through a journey based on your sales cycle, who you sell to, etcetera." 

Jake: “It's all about the people, man. I don't need to know the product that well. I don't need to really know much. All I need to do is to get to know Jake, or John, or Scott or Shawn, or Susan, or Eva, whatever. I think for a lot of people, if I understand where you are today, like what your motivations are, what you're trying to accomplish, then like, amazing. I can now help to put together a development plan because I can invest in you. “

Jake: "To understand where someone's coming from, I don't have to placate that person. I just need to understand so that I can better communicate with that person because now I know where they're at mentally or based on their experience. And then I show up consistently throughout the process. That's how I build rapport." 

Jake: "Really great coaching isn't always giving advice. Sometimes it's just asking."

Jake: "If you are doing something that you really enjoy, even when it's hard, you don't feel it, if I'm just being perfectly candid. I've been tired in my career and life, but once I realize that, look, I really love sales. I love learning. I'm naturally very curious. And sales to me checks those boxes in some next level because it's evolving so quickly." 

Jake: "If you align the things that you're good at and the things you enjoy and get energy from, that's the job you should be doing."

Jake: "Everyday is a chance to learn. Everyday is a chance to get better. Everyday is a chance to try new shit and break new things and try something different."

Jake: "100% if the problems you're facing have already been solved. Therefore, it is doable. So what are you gonna do about it?"

Jake: "I made an oath: I will never hang up the phone and have that feeling again. I will always go for 15 seconds of discomfort to ask that tough question, as opposed to 25 minutes or an hour, hours of beating myself up later, just knowing that I left something on the table, knowing that I left my best possible performance on the table."

You can learn more about Jake in the link below.

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.