Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on March 10th, 2021

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John Judge, SVP Sales, Crayon


Today we welcome John Judge who is Senior Vice President of Sales at Crayon.  Prior to joining Crayon, John was SVP of Sales at WordStream.  In his role at WordStream John led a team that doubled revenue resulting in the successful strategic acquisition of the company.   

John has been a sales and marketing leader across a number of successful technology companies, both large and small. Prior to WordStream he was Chief Revenue Officer for Datawatch, SVP for Enterprise Sales at Iron Mountain, and VP for Novell’s SUSE Linux business.

You can accomplish anything, provided you don’t mind who gets the credit – Harry Truman

JJ: Truman - Wasn’t told anything by the President as VP. Got news he should be at white house ASAP.  Found out the president had passed away and had to figure out what to do. He always took pride in delegating and didn’t need to take credit for all the stuff. I’ve always been a Truman fan and as a sales leader, any kind of leader. If you can delegate authority and coaching for improvement you are creating a culture to step out of the way of others*


How'd you get into sales?


Got into sales, had some people around me that I respected.  Uncle, heavy machinery sales guy who was also a real good golfer so took both of those up, good combo package. Parents saw my outgoing nature, competitive nature, swimmer. 

Butterflies in your stomach, feeling what it was like to win, just came natural. 

Took awhile to get good. First few forays into sales didn’t go so well, nearly got canned but finally pulled in the first


How do you manage the tension/stress/butterflies in your stomach feelings?


More mature in career now, a lot more chill than I was earlier in my career.

Have to have some level of perspective

Gained perspective in positive things and a few tragic things. 

I don’t care how bad a day you’re having selling, proposaling, closing. A heck of a lot out there worse that can be happening. 

CHILL, it’ll take care of itself. 

I like to compete, still like to compete.  Not running and swimming as fast but golf is fun!


Par 3 every time THIS ONE IS GOING IN! It’ll happen one day because that’s my attitude

Perspective and that RUSH of when it does go in, when then that deal goes in?

It’s FUN and you celebrate it. Make sure the people that deserve credit, get it!
It’s your legal, product, ops department, make sure you say thank you because they’re part of the team too.


Talk to me about how you celebrate victories and the wins with your team?


A lot has changed since everyone bugged out in March. 

TIMELINESS is important - the fastest you can get that High five!

SLACK → Everyone sees the deal come in, name of the rep, size of the deal

GONG Emails → don’t get credit until it’s sent to customer success. The gong emails are the whole company piling on with atta boys, bitmojis and have a lot of fun!

During pandemic working from home, everyday sales standup 5min/30 min depends on day. But we will have the celebrations everyday, promotions, hitting an anniversary 

I’m not the one that has to do it, others bring it up and it’s a great competitive culture and extraordinary teaming company. 

Some people have only been here through covid with no in-office experience rave about the culture.

Improved on culture during pandemic, everyone working for each other


Pre-Covid in-office culture, you wanted to see butts in seats.  You said “I don’t think I’ll go back to the office 5 days a week if I don’t have to” How do you see that operating after covid now?


Ran a boiler room, if you weren’t in seat at 9AM, you’re getting a text or a glare

Ran the organization in a traditional way, people fed off the energy, a lot of positivity came from it. 

When we bugged out (everyone had to go home). Having our business instrumented was important, every single key leading indicator is somewhere in salesforce or your dashboard of choice. 

Business was quickly instrumented so he could virtually “stand on the floor” and see all the metrics as to who is running which calls

Second, people can be very productive on their own! 

We have seen that people can be very successful in their home

“I’m a changed man, I have seen the light!”

We will go back to the office, socialization is missing, nothing like a live meeting, there are people stuck in small apartments. It’ll be nice, but there is more trust now that people can get things done on their own. 

Always sold over Zoom, so the client facing perspective was Hey put a background up on your Zoom call. 

Other than that it was on me to change.  Let’s adopt a new model. 


How do you build the culture for folks that have never been in office yet? The folks that haven’t been able to meet in-person.


Some folks don’t know how good it is in-person and this is all they know. 

We are big proponents of mental wellness. At least once a week we reinforce, help develop the proper healthy routines necessary to push through this. 

Whether we recognize it or not, everyone could be suffering from some level of depression or withdrawal. Need to recognize that. 


You’ve gotta look people in the eye. 

When we moved to 830AM Zoom standups, you could see some people nicked up. Had to set a standard:

  1. Cameras on
  2. Showered and ready
  3. No witness protection (blinded by background)

Some folks were saying thank you. Developing bad habits but not getting into that pattern. 

You’ve got to recognize this is a different time, focus on wellness, physical and mental. We’re alive, we still have a job, we have a lot to be thankful for, let’s celebrate that as much as we can.


We talked about ways you engage and motivate your employees.  Tell us more about how you play with the team and drive engagement. 


Blending physical wellness 

sNOw Days Off

Anyone who booked a deal got 20 pushups and he would do it and push it out to the whole team at WordStream

Crayon- ran a monthly competition. BDRs & Sales could play- successful BDR got a 30 second hill climb on the peloton while singing the song of her choice.  Miley Cyrus - Wrecking Ball (slight lyrical modification) On the 830 AM zoom call

For the top sales rep, Did a sprint saying SALES REP NAME IS GREATEST SELLER IN THE WORLD!

Sometimes you’ve got to give yourself up! If we got to 150% of quarterly number I Would shave my head! Got to 165%!

Quarterly meetings, flew down to ATL, right in middle of the meeting they brought in barber chair

Show some humility a smidge of self degradation, people will see that you will run through walls for them and they will then for you

Don’t make the job harder

Maintain your wellness and good spirits lean on others, they’re there for that

Tell the truth for how you’re doing how you’re feeling

Seek help when you need it

Got a lot of people saying no, don’t make it any worse on yourself


What does your daily routine look like to maintain performance?


Get outside everyday.  May not succeed everyday but it’s in the back of my head

Schedule time - get on the bike, get up and down the stairs

Work for a gentleman who loves to talk when he is on his daily jogs

14 degrees and still important to get outside!

Watch what you’re eating - kitchen is full of food, now I can just go downstairs and cook a steak

It’s the obvious stuff


How do you bounce back from a tough month/quarter or work with your leaders?


Over the years I’ve been consumed by the data. It’s all in the data. 

Why did close rate fall off? Couldn’t find our buyers?  Only had their office line and everyone was gone

It goes back to the fundamentals, not enough activity or opportunities tee’d up. 

Not enough adjustment in demos to account for key features

You can almost always get to an answer then focus in on that answer. 

Answers may differ from person to person. 

Must be instrumented to look at it from Crayon perspective, team and individual perspective

Any given cruddy month or quarter a few people who crushed it! → what happened with them that didn’t happen in other places that is micro focused in that manner.

Don’t do Sales ORG demo training anymore, do that with the people who need discovery work!

Get our best person at discovery to teach the class. You’re the one closest to success 

You’ve just got to own it 

“We’re/You’re better than this” Here’s what went wrong, what we’ll do to correct it and leading indicators to tell us if we’re moving in the right direction

OWN IT- we got a tough job

We will not win every month and every quarter as long as we win most of them, we’re going to be OK


Sales has so much data in today’s day and age. Going back to my days in baseball it’s a numbers games and you should be able to peel back the layers of the onion to understand where the opportunity is. 


As leaders we have to be ready to have difficult conversations and EMBRACE THEM. 

If you allow disorganization or poor performance or something wrong with an individual's results and kick that can down the road, that leads to significant dysfunction. 

Have to be able to sit folks down, do it on a caring way, focus on the problem not the person and be CARING ABOUT IT 

When you first met JJ, was he impressed with how good you were? → Yep congratulated me on another record month → showed me my call stats and new biz generation → told me to get my butt in gear because 2 months from now will stink → now seen as the right thing to do!

Have to have those conversations as leaders to problem solve, still LISTEN back.


Help people be their best, be uncomfortable for 5 seconds, maybe 1 minute. 


The Power of No

Prospect starts asking for more. The answer is NO, we can’t offer that. Then ZIP IT! No explanation needed. The classic, next person to speak loses!

Be comfortable saying NO. It’s PERFECTLY OK TO SAY NO!


What are some of your qualities in leaders you love?


I love an individual who is Self-reflective, generates a genuine level of humility because people respond well to that

A leader that has proven they can walk the walk. Last 3 companies “we’re gonna grow our own leadership” The street cred that you can have by being senior sales exec, team lead, manager, and ascend to leadership role. Significantly overcomes the, we need new blood, which can help. 

To have a management team that has risen up has so much street cred and power. They also know how to get everything done, they know how to make the flywheel fly!

Extremely motivating and powerful retention tool as the organization expands as you work towards unicorn status. People know I have a shot at that next promotion!

I look for qualities I see growing up in people as they expand the organization. 

I’m gonna let you try it out, be a team lead, try it out, carry your bag and see how it fits. 


As we think about organizational growth and development.  REtention of employees and talent is critical.  If you can bring individuals that can be self-reflective, have humility and see a future for themselves is a fantastic way to keep people. 

Do you love winning or hate losing?


I like Winning more and enjoy people that like winning more.  It allows you to let go of the negative/losing quicker. 

The people that hate losing tend to get a little grindy and sit on the 1 deal of 5 they lost. 

It’s a lot more fun celebrating success than it is going through loss meetings. 

I LIKE WiNNING! I don’t remember the 2nd, 3rd, 4th places.  But I can remember the #1 times! 

I like to see people touch the wall first and celebrate those


Favorite interview question


I have a couple things I like to do in interviews.

3 Sections - I’ll let you ask questions first - Knock them off balance. And see the quality of their questions. 

Tell me what your greatest attribute is? And What's' your current area of professional development. -- The first one doesn’t matter, it’s all about question #2. 1. Do they remember the question? 2. Do they give me an honest answer or some sort of rope a dope answer. 3. They give me honest answer 


I get to find out whether I have someone who is; honest, has emotional intelligence and whether they have the skillset to go improve upon something. 

We are all always improving on something. 





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.