Account Executive

Crayon
Boston, MA

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.

Requirements

  • 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

Benefits

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.

On-Target Earnings: $200k+

Posted 2025-08-09

Recommended Jobs

Associate Teacher (SY25-26, Middle School)

Veritas Preparatory Charter School
Springfield, MA

What You’ll Do As an Associate Teacher (AT) at Veritas Prep, you will join a supportive, team-oriented environment designed to foster your growth as an educator. In this role, you’ll play a key pa…

View Details
Posted 2026-02-11

Certified Personal Trainer, Physical Education, Recreation, and Dance

Boston University
Boston, MA

We seek personal trainers with current national certification from NSCA, ACSM, ACE, AFAA, or similar nationally accredited organizations. Compensation: $25 - $30 an hour $6,500 – $15,600 per y…

View Details
Posted 2026-04-06

Customer Service Representative

Window World of Boston
Woburn, MA

Job Description Job Description Company Overview Window World is the largest exterior remodeler in the United States and we are looking for highly motivated professionals to offer a best-in-cl…

View Details
Posted 2026-03-20

Senior Manager, Consulting

Dana-Farber Cancer Institute
Brookline, MA

Overview Job Profile Summary The Senior Consulting Manager supports large-scale transformations at Dana-Farber as well as planning and decision-making regarding the company’s most critical bu…

View Details
Posted 2026-04-27

Principal Scientist, Peptide Chemistry (Boston)

Third Rock Ventures
Boston, MA

About the Company A soon to launch Third Rock Ventures company is seeking an experienced Peptide Scientist to lead peptide design efforts supporting discovery-stage therapeutic programs. This role…

View Details
Posted 2026-04-27

Seasonal Special Police Officer

The Trustees of Reservations
Ipswich, MA

Who We Are: Founded in 1891 by a group of visionary volunteers, The Trustees of Reservations (The Trustees) is the nation’s premier conservation and preservation organization. The Trustees’ preser…

View Details
Posted 2026-01-14

infant/ Toddler Teacher

The Goddard School
Bedford, MA

Job Description Job Description The Goddard School of Bedford is a place where children learn through play in a fun and nurturing environment. The Early Childhood Educator develops and implements…

View Details
Posted 2026-04-17

Prep Cook

Mother's East Tavern
Boston, MA

Job Purpose: Perform assigned responsibilities necessary for production of food items for the restaurant, in keeping with the standards of food quality, sanitation and cleanliness. Duties & Res…

View Details
Posted 2026-04-17