Jessie Jackson

Trailblazer
DISC Type : DI

Chief Digital Officer - Digital Strategy Leadership at Jess Jackson Consulting

New York City Metropolitan Area, United States

Overview

Jessie Jackson is a digital commerce leader with over 20 years of experience driving growth for major retail and B2B brands. As Chief Digital Officer at her consultancy, she specializes in strategy, customer experience, and technology implementation. Colleagues describe her as results-driven, thorough, and passionate.

Outside of her consulting work, Jessie is focused on mentorship and fostering authenticity. She actively supports professional communities that help those affected by layoffs and uses her platform to advocate for individuals finding and using their unique voice in their careers and lives.

After working at Victorias Secret for 20 years, she took a chance and reached out to Mickey Drexler, who then hired her to run J. Crews e-commerce.

Personality Overview

Persuasive

Friendly But Fast

Informal

They respond better to a combination of speed and relationship.  They are charming and have the ability to align others behind their decisions. They like to keep things under control.

Topics They Care About

Customer Experience
Her work is centered on the belief that a better customer experience directly translates to better business performance, a core tenet of her consulting practice.
Digital Commerce Strategy
With over two decades of leadership, she focuses on P&L management, strategic roadmaps, and re-platforming for clients like Puma, GameStop, and Canada Goose.
Authentic Leadership
She frequently posts about the value of using one's authentic voice and ideas, believing an individual's unique perspective is a significant business asset.

Media Appearances

Jessie has no verified media appearances

Work History

8-2024
Chief Digital Officer - Digital Strategy Leadership at Jess Jackson Consulting
1-2022 - 10-2024
Digital Strategy Practice Lead at OSF Digital
1-2019 - 12-2021
Senior Consultant at FitForCommerce LLC
5-2018 - 1-2019
Senior Director, E-Commerce & Mobile at The Vitamin Shoppe
8-2015 - 1-2018
Sr. Director, E-Commerce at Rebecca Taylor

Education

1983 - 1987
BA from New York University
1982 - 1983
Education details unavailable from Antioch College

More Information

Social Presence :

Prographics :

Exp : 12 Location : New York City Metropolitan Area, United States Job Level : Leadership Designation : Chief Digital Officer - Digital Strategy Leadership at Jess Jackson Consulting
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Insights For Selling To Jessie

During A Call Or A Meeting

DO's

  • Talk about yourself and some of your achievements at the start of the conversation
  • Ask them for a lunch or coffee once some rapport has been established
  • Showcase existing customers and use case-studies to grab their attention

DONT's

  • Don't make any commitments that you might not be able to fulfill
  • Avoid unnecessary negativity or slowness
  • Do not look like someone who doesn’t know what they are talking about

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 make decisions quickly if they develop trust in you and conviction 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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