Our Fireside Fridays series is where we have the opportunity to sit down with top B2B revenue leaders for 7 questions and get a behind-the-scenes look at their recommended best practices, their background, and factors that have contributed to their success.  This is our interview with John Judge, SVP of Sales at Crayon.  

Give us your background in sales

I’ve been a sales and marketing leader across a number of successful technology companies, both large and small. Prior to Crayon, I was SVP of sales at WordStream where we successfully sold the company to a strategic buyer. In addition; I’ve been Chief Revenue Officer for Datawatch, SVP for Enterprise Sales at Iron Mountain, and VP for Novell’s SUSE Linux business.

What’s the best piece of sales advice you ever got?

“When you’ve earned the right to ask for the order… ASK for it”. First sales VP I ever worked for gave me that and I’ve never forgotten it, not do I ever fail to pass that on to my teams.

What is the biggest challenge today facing a sales professional, and how would you recommend they overcome it?

I’m not a person of “absolutes”… so the term “biggest” is tough for me to answer. A few biggies I see working alone at home in the Pandemic, dropping into occasional ruts and bad habits, and thinking the grass is greener somewhere else. For all of these I continually as my sales pros: “Are you getting what you need from your boss?” “Are you happy with your company, your team and your leadership?” “If you were me, what would you do right now?”

What’s the best sales or business book you’ve ever read?

Challenger Sale. Right now I’m lost in a Mitch Rapp series of books on international intrigue. (I need to shut my brain off at night!)

What’s the best advice you’d give to someone who is interested in getting into leadership one day?

Few things: Do the job you have right now really, really well. Find a mentor who will give you honest advice on the areas you need to work on… and work them. Have a plan developed with your leadership on the path you need to travel in order to win that leadership position. Remember also: the best salespeople don’t always make the best leaders. Learn the craft of leadership along with the craft of selling.

What’s a mistake or fail you vividly remember from your journey in business, and what did you ultimately learn from that experience?

Jumping to conclusions too quickly. Did it once and it cost me my role as a regional leader. Was fortunate enough to work for a person who eventually saw that I learned from that mistake and was given an even better role a year later.

What is one weird/quirky think about you that most people don’t know?

I am freakishly good at landscaping.
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