Hightail, formerly YouSendIt, is a cloud service that lets users send, receive, digitally sign, and synchronize files.

The company's early focus was on helping users send files that were too large for email; it started adding features and plug-ins for businesses in 2007.

[4] In its early years, Amir pursued advertising revenues, Jimmy Vienneau managed business development, Francis Wu created the graphic design including the logo, while Kumaran focused on the user experience and Khalid did technical work.

[24][25] In September 2013, Hightail acquired adeptCloud, a security-focused file-sharing service for hosting files inside a corporate firewall.

[41][42] The service has a pay-per-use security feature[5] and files sent through Hightail are encrypted during transit and while stored on individual devices or servers.

[44] The business version has additional features for corporate use, such as remote data wipes on mobile devices, service level agreements and controls for compliance requirements, such as HIPAA and PCI.

[53] In July, YouSendIt's online folder management system and digital signing features were introduced in order to compete with Dropbox.

The reviewer, Jeffrey Wilson, found its app easy to use and noted its digital signing and cloud storage features.

Wilson reported problems when trying to use the digital signing feature with the phone held vertically and experienced occasional crashes.

"[58] A review in About.com said the service was easy-to-use and noted its features for password protection, file-tracking and interface branding, but also pointed out that users cannot copy themselves on files sent through the Hightail Outlook application.

[60] Referring to the "for Business" product, PC Advisor stated that Dropbox, had better customization, while YouSendIt had the advantage of integration with SharePoint and Active Directory for corporate environments.

[61] Enterprise Strategy Group (ESG) conducted a comparative review of vendors in the file sharing and collaboration market in 2012.

ESG noted that the pricing model was expensive on a per-user basis, but its lack of caps or surcharges made it more affordable for heavy users.