Jonathan Czaja

CEO & Owner

Freebird

Sep 2025 - Current (1 year)

Freebird makes handcrafted leather boots. I purchased the business in Dec 2025.

CEO & Owner

The Pros Closet

Sep 2023 - Current (3 years)

The Pro’s Closet sells high-end used bikes. I purchased the business in Dec 2025.

Chief Operating Officer

Skupos Inc

Sep 2020 - Sep 2023 (3 years 1 month)

Skupos develops software for 15,000 convenience stores in the US (10% of the market). Grew sales by 3x and sold to our largest competitor. Backed by Insight Partners, Toba Capital, Dynamo Ventures, and Unilever Ventures. Acquired by PDI Technologies in August 2023.

Chief Operating Officer

Nurx

Sep 2018 - Feb 2020 (1 year 6 months)

Nurx is a $100m+ telemedicine startup that prescribes and delivers birth control through an app. Led a team of 150+ doctors, nurses, pharmacists and CX reps in SF, Miami and NY. Backed by Kleiner Perkins and Union Square Ventures. Merged with Thirty Madison in 2022.

VP Operations

Stitch Fix

Sep 2015 - Sep 2018 (3 years 1 month)

Stitch Fix is $1bn+ online apparel business. Responsible for 6 warehouses and 2,000 employees. Opened 4 warehouses, grew the team by 3x, and acquired a knitting mill and sewing factory in Reading PA. Stitch Fix went public (Nasdaq:SFIX) in 2017.

Director, Small Business Advertising (North America)

Facebook

May 2014 - Oct 2015 (1 year 6 months)

Responsible for building world-class customer service to help over 2m small businesses advertise on Facebook. Led a team of 100+ in North America focused on account management, customer service, marketing and events. Also responsible for customer service globally with operations in Austin, Dublin, Sao Paulo and Singapore.

Chief Operating Officer

Bonobos

Apr 2012 - Apr 2014 (2 years 1 month)

Responsible for manufacturing, fulfillment, transportation, customer service and website operations. Led a team of 60+ in New York and Hong Kong. Bonobos was awarded "Best Customer Experience" and "Best Returns Experience" by Multichannel Merchant in 2015. Bonobos was acquired by Walmart in 2017.

Director, Operations

Walmart eCommerce

Jan 2010 - Apr 2012 (2 years 4 months)

Responsible for the reverse logistics and customer advocacy teams (12 people, $70m+ in expense). Relocated to Shanghai to help launch Walmart.com China.

Sr. Category Manager

ebay

Jun 2008 - Jan 2010 (1 year 8 months)

Business manager responsible for the Clothing, Shoes & Accessories category.

Sr. Business Manager

Walmartcom

Feb 2007 - Jun 2008 (1 year 5 months)

Responsible for the online Pharmacy and Tire retail categories.

Analyst, Private Equity Group

Merrill Lynch

Jun 2001 - Jul 2004 (3 years 2 months)

Investment professional in $2.0 billion private equity fund. Evaluated investments in the manufacturing, technology, media, and retail industries. Lead analyst on $700m buyout of Atrium Corporation.

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