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There have been a couple recent updates I'd like to suggest adding to the article to keep it up to date
Suggest adding right after "placing it in competition with Dropbox Inc. and Box Inc.": “Hightail began advertising against competitors Dropbox and Box with slogans like "Your files should be neither Dropped nor Boxed".<ref>{{cite news|title=Silicon Valley's billboard wars are back|first=Ari|last=Levy|date=July 14, 2014|url=http://www.cnbc.com/id/101832454#|publisher=CNBC|accessdate=August 1, 2014}}</ref>
Suggest adding to the very end of the History section: "Brad Garlinghouse resigned as CEO in September 2014 allegedly due to disagreements with the board of directors and was replaced by co-founder Ranjith Kumaran.<reF>{{cite news|publisher=re/code|url=http://recode.net/2014/09/12/why-brad-garlinghouse-left-hightail/|title=Why Brad Garlinghouse Left Hightail|date=September 12, 2014|accessdate=September 16, 2014}}</ref>
One thing I should point out regarding Garlinghouse's resignation, is that the source goes into great depth about the circumstances of his resignation based on "sources familiar with the matter" and to what extent (if any) it should be included might be debateable. I just included it briefly with the "allegedly" statement. CorporateM (Talk) 23:54, 16 September 2014 (UTC)[reply]
YouSendIt, later HighTail, while for a short time unbeatable and unavoidable, has had its lunch well and truly eaten (in Europe at least) by WeTransfer. Nobody in Europe willingly uses YouSendIt any more. Everyone uses WeTransfer. Should we mention this? 2A02:1811:429:F200:8973:F490:4575:CDE2 (talk) 19:35, 17 August 2015 (UTC))[reply]
Hawes, Larry (October 16, 2015). "Hightail to a Defensible Niche". Gigaom The industry leader in emerging technology research. Retrieved February 2, 2016.