Jessie Carroll in

Jessie Carroll

Trailblazer · DISC type DI
Director, Support Content at Squarespace
📍 New York City Metropolitan Area, United States

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.

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Experience
18 Years
Current Role
Director, Support Content
Job Level
Mid-senior
Location
New York City Metropolitan Area, United States
Personality Overview

How Jessie shows up

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.

Priorities

Topics Jessie cares 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.
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Career

Work history

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

Media appearances

No media yetWe could not find public media appearances for this person.
Education
BS
Ithaca College
Education details unavailable
New York University School of Continuing and Professional Studies
Social presence
in
Behavioral profile

DISC profile (public)

D

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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