Career Path - Chris Pope, Director of Sales at Crayon banner image

Career Path - Chris Pope, Director of Sales at Crayon

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What do the career path and the day-in-the-life look like for a Director of Sales at Crayon?

We connected with Chris Pope to find out!

Interested in learning more about Crayon? Make sure to check out their company page!

Where did you grow up? What did your parents do for work?  

I grew up in Newfields, NH which is a small town in southeastern NH. My mom has worked in sales at Microsoft for almost 30 years and my dad has held a number of jobs including managing manufacturing plants, coaching every youth sport you can imagine, and helping manage a golf course.

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I graduated from Hobart & William Smith Colleges in Geneva, New York with a degree in Public Policy and English. I initially worked as an apprentice for Kerivan-Lane, which is a family-owned HVAC business out of Needham, MA. That opportunity was humbling and really opened my eyes to the real world and taught me a lot about hard work and customer service. It also taught me that manual labor wasn’t something I wanted to spend the next 50 years of my career doing. After my time there, I started my career in sales at AppNeta, working for the brilliant Matt Stevens. I attribute a lot of the sales skills and knowledge I have to my time there. They were a gritty start-up at the time that wasn’t afraid to provide young people with the opportunities to grow their careers quickly. While sometimes you felt like you were drowning, I also credit the sales leaders there for teaching me how to swim pretty quickly. Since then, I have been at Crayon for the past 4.5 years, where I have grown from Account Executive to Director of Sales. I think I was extremely fortunate to find Crayon when I did. It’s not every day you get to watch a start-up go from doing thousands of dollars worth of business to tens of millions of dollars worth of business first-hand in such a short period of time. It’s been the ride of a lifetime, to say the least.

Chris Pope Crayon

What has attributed to your success thus far and has helped propel you to the position you have now?

I have two mantras:

  • Always be the hardest working person in the room (or on the Zoom)
  • Be an expert

Sales takes a lot of skill, but part of it is science. The harder you work, the more successful you will be. My dad drilled into my head at an early age that if you want to be a leader, you need to lead by example, so that is always what I have tried to do. 

I think one of the most common mistakes salespeople make is not taking the time to become an expert of their product and their industry. Sales is all about trust and showing your prospects you are an expert can go a long way in your attempt to build credibility. One of the first things I did during my time at Crayon is quickly form alliances with every department within the organization, as well as become acquainted with a lot of thought leaders in the industry.

Can you share the high-level responsibilities of your current position as a Director of Sales at Crayon?

Most of my time is spent supporting our senior sales executives with deal support. Whether that is providing technical support on demonstrations or strategizing around negotiations and internal contract review processes. I also assist with hiring, onboarding, and training of new sales executives, as well as other strategic initiatives we have going on internally.

Any tips for someone considering a career in your field?

Network. Network. Network. Immerse yourself into the fast-growing technology community and build as many relationships as you can.

Chris Pope Crayon 1

Day in the Life

Coffee, tea, or nothing?

I crush caffeine-free tea to help me keep going through the day. 

What time do you get into the office? 

Typically between 7:30-8:00 am.

What are three things that motivate you in your role?

  • Seeing others succeed
  • Watching the company succeed
  • Money

Every day is different, but can you outline what a typical day looks like for you?

I am in the trenches with my team.  With a team of reps that vary in tenure and experience, I never know what my day will end up being.  From scheduled demos to last minute negotiations, things move fast and so do I. 

What time do you head out of the office? 

Typically at 6pm 

Do you log back in at night or do you shut it down completely?  

It’s a mobile world, so I am pretty much always on or available. I usually take one or two vacations per year where I try my best to shut it down completely. 

Any productivity hacks?

  • Take short breaks throughout the day. I am almost always pacing from one end of our office to the other between tasks. 
  • Plan your next day the night before. I wrap up every day by creating a to-do list for the next day.
  • Work on one big project at a time. 

What are the 3 apps that you can’t live without?

  • The Grint - So I can closely monitor how bad my golf game is. 
  • ESPN
  • Instagram

Who do you admire or call upon for professional advice?

I have a ton of mentors and peers I call or share ideas with frequently. If you don’t have a career mentor, I strongly suggest speaking to your manager about helping you find one.

About the

Crayon’s award-winning competitive intelligence platform helps your organization see and seize opportunities so you can create a sustainable business advantage.

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