Customer Success Manager

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

As a Customer Success Manager at Crayon, you'll be a strategic partner to our customers by helping them harness the full potential of Crayon’s capabilities to build a best in class competitive intelligence program. You’ll also play a key role in scaling Crayon’s customer business, by driving retention and growth of our clients.

You'll draw on your business, sales, and technical acumen to gain a deep understanding of their business objectives, strategic direction, AI vision, and technical needs to advise them through their journey with Crayon.


You will also get to function at the tip of the spear for all new product releases, helping with everything from go-to-market strategy to narrative creation. You’ll have a key voice in shaping how we build and deliver ongoing value as a business. Our vision is to become the best CS team in all of SaaS, and we’re looking for the next person who can bring us closer to that vision.

What You'll Work On

  • Driving adoption, retention, and expansion for a product that solves real problems.
  • Proactively own the customer experience across their lifecycle — managing comprehensive account and success plans grounded in the customer's business objectives, serving as the primary conduit between the customer and Crayon to help them drive organizational impact with their Compete program.
  • As the customer's trusted advisor and product expert, You'll host trainings, onboarding, and working sessions to educate our customers and dig deep into new use cases of Crayon.
  • Contribute to the foundations of Customer Success at Crayon. As a member of our small but mighty team, you’ll be instrumental in helping define our motion.

Requirements

  • You have 2+ years managing B2B SaaS accounts focused on retention and growth.
  • You have strong project management skills & ability to manage multiple customer relationships.
  • You have the ability to navigate ambiguity in a fast-paced environment.
  • You have a “roll up your sleeves” mentality and are committed to driving results.
  • You’re a cross-functional collaborator. You proactively and positively represent your customers and their needs internally, and are excited to rally everyone around strategies that solve their needs.

Benefits

We offer a competitive base salary and bonus structure that includes a meaningful equity component. CSMs 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.

Posted 2026-01-14

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