OpenSky

OpenSky, which now operates as Alibaba.com's North America and Europe division, was established in 2009 by co-founders John Caplan, Kevin Ambrosini, and Alan Blaustein. Caplan, who served as CEO, brought a wealth of experience from previous high-profile roles, including CEO of Ford Models and President and CMO of About.com. His background in marketing and brand development, with involvement in major brands like Starbucks and Arizona Iced Tea, shaped OpenSky's strategic direction.

Initially launched as a social shopping platform, the company pivoted to a model centered around curation by experts and celebrities. The platform enabled tastemakers, such as Bobby Flay and Serena Williams, to recommend products to their followers, with OpenSky taking a percentage of the sales. Another key aspect of its business was providing tools for bloggers to monetize their content by selling products directly to their audience. This approach targeted consumers looking for a more personalized and interest-driven shopping experience, differentiating it from large-scale retail. The company operated a web and mobile marketplace where users could discover and purchase goods aligned with their tastes.

OpenSky secured significant financial backing, raising a total of $49.4 million over four funding rounds from investors such as Providence Equity Partners, Highland Capital Partners, and Canaan. A major funding event was a Series C round in October 2011, which brought in $30 million. The path to acquisition began in 2015 when Alibaba acquired a 37% stake in the company. This was part of a larger deal where OpenSky absorbed several Alibaba-owned entities, including 11 Main, Auctiva, and Vendio. The relationship culminated in a full acquisition by Alibaba Group, which was completed on September 5, 2018. Following the acquisition, the OpenSky team and its marketplace and SaaS businesses were integrated into Alibaba, forming the foundation of Alibaba.com's B2B operations in North America and Europe.

Keywords: social commerce, curated marketplace, influencer marketing, e-commerce platform, SMB enablement, celebrity endorsements, B2B trading, online retail, SaaS for merchants, Alibaba acquisition, John Caplan, Providence Equity Partners, Highland Capital Partners, social shopping, product discovery, digital marketplace, online monetization, retail technology, venture capital, e-commerce acquisition