Jessie Carroll

Trailblazer
DISC Type : DI

Director, Support Content at Squarespace

New York City Metropolitan Area, United States

Overview

Jessie Carroll is the Director of Support Content at Squarespace, where she builds high-performing content teams focused on scaling knowledge and elevating the customer experience. People who have worked with her often describe her as reliable, dedicated, smart, and a talented writer. She holds a BS from Ithaca College and is a Certified Professional Resume Writer.

Jessies work centers on the intersection of technology and user support, with a keen interest in the evolving role of AI in customer self-service. Her career demonstrates a consistent focus on developing writers and managers, creating systems that support growth and adapt to change in the tech landscape.

Unique fact: She received the Erin Masling Faculty Award in college, given to one graduating senior for demonstrating a commitment to learning and overcoming significant challenges.

Personality Overview

Values Relationships

Charismatic

Informal

They are more likely to be open to unproven but exciting technologies.  They are charming and have the ability to align others behind their decisions. They will fight for you if they come to believe in you.

Topics They Care About

AI in Customer Support
Her work involves deploying AI tools and navigating its evolving role in customer support and self-service, as mentioned in her recent hiring posts.
Content Team Development
Focuses on building and coaching content teams, helping managers and writers grow their skills and advance their careers.
Scaling Knowledge Systems
Her experience includes leading multiple CMS migrations and building content standards to scale knowledge for a growing customer base.

Media Appearances

Jessie has no verified media appearances

Work History

8-2025
Director, Support Content at Squarespace
10-2021 - 8-2025
Senior Content Team Manager, Customer Operations at Squarespace
1-2018 - 10-2021
Content Team Manager, Customer Operations at Squarespace
4-2014 - 12-2017
Content Team Lead, Customer Operations at Squarespace
2013 - 2014
Content Development Manager at Booker Software

Education

BS from Ithaca College
Education details unavailable from New York University School of Continuing and Professional Studies

More Information

Social Presence :

Prographics :

Exp : 18 Location : New York City Metropolitan Area, United States Job Level : Mid-senior Designation : Director, Support Content at Squarespace
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Insights For Selling To Jessie

During A Call Or A Meeting

DO's

  • Keep your pitch focused on the impact but nurture the relationship too
  • Talk about yourself and some of your achievements at the start of the conversation
  • Build a trustworthy relationship while keeping the product center-stage

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Avoid unnecessary negativity or slowness
  • Don’t force involvement of other stakeholders unless it is critical

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jessie is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Jessie

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Jessie move?

  • They can reach decisions quickly if they develop trust and confidence in the product.
  • Can Jessie take some risk or not?

  • They can take risks if necessary.

You And Jessie

Personality Compatibility


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