071 – Breaking Through with Voice in a World of Automation | John Jackson

071 – Breaking Through with Voice in a World of Automation | John Jackson

Born and raised in Lima, Peru, John Jackson felt in order to be successful, he had to be educated in the United States. Combine that with his parent’s subscription to National Geographic magazine and he soon found his way to living in Pennsylvania.

A failed stent selling pots and pots door to door nearly caused John to give up sales. In fact, after finishing basic training for the Army, John told an employment agency he wanted to do “anything but sales.”

Fortunately, John’s charisma kept him in the game where he’s found success over and over again for the last 30 years. Today he keeps up his “old school” success as Director of Sales at Connect and Sell, a platform he calls the “Uber of Sales.”


  1. Blaze a Different Path: I’m a big proponent of starting outreach as high as you can in an organization. However, when you can’t reach that person, you have to try a different approach. Figure out who the direct reports are for the person you ultimately want to connect with and try to build a relationship with them. Doing this correctly could help you gain valuable insight on initiatives, priorities, communication preferences and even the decision making process.
  2. Don’t Rely on Others: Your success is just that — your’s. It shouldn’t come from peers, another department, or even your manager, it must come from within you. Having that mentality will help you overcome many obstacles. Don’t have enough data or prospects on your call list? Find it elsewhere. Don’t have all the answers to objections? Research your prospects to understand the root cause of their statement. Don’t have all the tools you need to do your job? Buy them yourself.
  3. Never Give Up: Unless a prospect tells you they’ve left the company they work for or the company is going out of business, don’t give up on them. Simply hearing “no” today does not mean “no forever.” After six months, figure out what has changed with the person, their company, or the use case you solve for and reach back out.

Book Recommendation


  • CostelloWhat if every sales rep inherited the habits of your best rep? With Costello, they do.
  • The pipeline-centric system is strategically built on a proven selling methodology that keeps teams focused on the only thing they can control in sales – actions that push deals to close.

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