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The Winston Box


Workforce History:

In an effort to provide more fashion options for the “Big and Tall” community, owner Wil Cuadros and CEO Amit Patel created The Winston Box in 2016. The Winston Box is a subscription box service, dedicated to serving individuals who have trouble finding clothing in their sizes through more traditional methods. The company makes all its goods in Peru, ensuring that customers receive quality merchandise for the price they pay.


Workforce Challenge:

In July of 2018, The Winston Box began its partnership with SBWIB through a generous clothing donation to SBWIB’s Career Pathways 180 prison-to-employment academy. The Winston Box donated dress shirts and pants for participants of the academy that were worn at the conclusion of the training at the CP 180 job fair, in which participants interviewed with several employers. In May of 2019, The Winston Box agreed to serve as a worksite for SBWIB’s youth Paid Work Experience (PWEX) program, in which it has hosted youth from the Gardena One-Stop and provided valuable work experience, training the youth in order fulfillment, customer service, and social media marketing.


Outcomes & Benefits:

Successful order fulfillment has been a significant challenge for The Winston Box. However, through partnering with SBWIB and serving as a worksite for the youth Paid Work Experience (PWEX) program, SBWIB has been able to provide the company with reliable youth workers who have successfully assisted with fulfillment, packing, sorting, and order tracking.

The company has seen an increase in staff around the warehouse, which has resulted in an increase in order fulfillment and productivity.

“This is a great opportunity for small businesses and an equally great way to give back to the community.”

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