Demo

Account Executive

Crayon
Boston, MA Full Time
POSTED ON 4/16/2026
AVAILABLE BEFORE 5/15/2026
About Crayon

Deals are more competitive than ever! 55% of companies say they have more competitive deals than they did a year ago, and sellers are facing competitors in nearly 7 out of every 10 deals. 

And yet the typical company rates their effectiveness in competitive selling just a 3.8 out of 10 — a painful reminder that most teams are losing head to head competitive deals they should be winning. 

In fact, the typical enterprise is losing $2 to $10 million a year in competitive deals they could have won!

At Crayon, we literally fix this.

We're building software that helps sales teams win competitive deals at a higher rate. This is a problem that had been waiting for AI to come along. Our software transforms mountains of unstructured data into actionable, winning sales plays and deadly talk tracks. We do it in real-time, at-scale, using AI.

If you want to build something big and you’re passionate about how generative AI is transforming go-to-market, we’d love to meet you!

About the role and team
  • You will close opps generated by our marketing and SDR orgs, but we also expect you to own ensuring you have enough pipeline to hit your number.
  • We are extremely development focused. Weekly training session. Lots of call reviews. 1:1 coaching. Feedback heavy culture. (make sure you’re really excited about this)
  • High performing. We brought in new leadership and reset our team a bit in H2 2024 and have seen consistent over-achievement of team and individual targets.
  • Attributes we look for in sellers: smart, high EQ, seriously hard working, high agency
  • We like sellers who have ideas, who will refine their own talk tracks and share them back to the team, who are always tinkering with messaging and collateral
  • Crayon is a startup. We change things all the time in a never-ending quest to be the most elite team we possibly can.
  • We’re open minded, but we’re looking primarily for folks with at least some experience in an Account Executive role
  • You must have a demonstrated track record of high performance professionally and throughout your life
  • Serious work ethic
  • Hunger for feedback and to improve your own craft (we approach training like a professional sports team)
  • Smart, ready to present as a peer to serious executives
  • Excellent ability to connect with people
  • High agency, meaning you just find a way to accomplish the mission
  • High integrity
  • Excellent writer

We offer a very competitive base salary and commission structure that includes a meaningful equity component. Crayon AEs who demonstrate high performance and commitment also have the opportunity for rapid career development within sales or other departments.

Crayon offers medical, dental, vision, 401k, generous paid parental leave, and take-what-you-need paid time off.

Salary : $2 - $10

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Job openings at Crayon

  • Crayon Boston, MA
  • DescriptionAbout Us Sales deals are more competitive than ever, but most sales reps aren’t prepared to sell against the competition. At Crayon, we're build... more
  • 10 Days Ago


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