Gypsy Jo Diessner

VP of Engineering

Rogers, Arkansas, United States24 yrs 11 mos experience

Most Likely To SwitchHighly Stable

Key Highlights

20+ years of retail leadership experience
Expertise in eCommerce and merchandising strategies
Proven track record of driving business growth

Stackforce AI infers this person is a Retail and eCommerce expert with a strong focus on merchandising and digital strategy.

Contact

Skills

Core Skills

EcommerceMerchandisingProduct DevelopmentInventory Management

Other Skills

site buyingplanningsite experience strategyphoto studio managementbusiness growthonline exclusivessite relaunchreplatformmobile launch3PL transitionsomni editorialmarketing messagingwholesale merchandisingbusiness launchcollaborations

About

Highly strategic, results-driven merchandising and digital leader with 20+ years of experience leading complex retail businesses. Deep roots in fashion—one of the few retail categories that spans trend-driven storytelling, seasonal demand, replenishment basics, and high-consideration purchases—providing a strong foundation for customer-centric leadership at enterprise scale. Delivers outsized growth with urgency and clarity through periods of change. Builds high-performing teams and strong cross-functional partnerships by setting north star, establishing trust, and focusing on talent development.

Experience

24 yrs 11 mos

Total Experience

6 yrs 3 mos

Average Tenure

10 yrs 6 mos

Current Experience

Walmart

5 roles

VP Merchandising - Kids & Baby Fashion

Feb 2026 – Present · 3 mos

VP Merchandising, Kids Fashion

Jun 2023 – Feb 2026 · 2 yrs 8 mos

VP, DMM Shoes

Promoted

Apr 2020 – May 2023 · 3 yrs 1 mo

GM Kids and Baby Apparel (eCommerce)

Promoted

Feb 2017 – Mar 2020 · 3 yrs 1 mo

Senior Director, DMM - Ladies Apparel, Jewelry, and Accessories (eCommerce)

Sep 2015 – Feb 2017 · 1 yr 5 mos

Charlotte russe

DMM eCommerce

Mar 2010 – Aug 2015 · 5 yrs 5 mos · San Francisco Bay Area

Quadrupled ecommerce business in 5 years.
Lead site buying, merchandising, planning, and site experience strategy. Oversaw photo studio in 2012.
Grew online exclusives to 50% contribution and launched new initiatives (plus size, premium, and brands).
Business lead for site relaunch (2010), replatform (2012), mobile launch (2013), and 3PL transitions (2012, 2014).
Drove omni editorial and marketing messaging.

eCommercesite buyingmerchandisingplanningsite experience strategyphoto studio management+8

Levi strauss & co.

Merchandising

Jan 2008 – Jan 2010 · 2 yrs

Lead premium wholesale and retail merchandising for the Americas region.
Key lead in global transition and partnered with Asia and Europe teams on product development.
Launched new businesses: Best of Red Tab, Project X, and collaborations (Obey, Opening Ceremony, J. Crew).
Oversaw Childrens business for US Retail stores.

wholesale merchandisingproduct developmentbusiness launchcollaborationsretail merchandisingmerchandising

Gap inc.

Merchandising

Jan 2001 – Jan 2008 · 7 yrs

Accelerated growth in kids and baby business by expanding and elevating assortment and in store merchandising, testing, building flexibility through fabric platforming, and improving in stocks and sell-throughs (2005-2008).
Launched Maternity online and rolled out to over 300 retail doors (2001-2005).
Served as merchandising lead in inventory management transition and divisional lead for marketing and promotions.

inventory managementmarketingpromotionsmerchandising