Team collaboration

Day one of building a new brand

To say that I’ve been thinking a lot about branding lately is something of an understatement. From the moment I joined the company, the idea of changing YouSendIt’s name has been the subject of much deliberation and discussion. After all, changing the name of a well-known service used by over 40 million people is not something to take lightly.

Name changes are often the refuge of companies looking to escape a less-than-glorious past, such as Blackwater’s rebranding as Academi following its controversial involvement in the Iraq War. But there are also many successful name changes made by businesses that, like YouSendIt, simply outgrow their original (often descriptive) moniker.

As it grew spectacularly in 1997, AuctionWeb changed its name to eBay — a less descriptive but ultimately inspired choice that allowed the brand to expand into a wide variety of retail operations. Popular music site Pandora started life as Savage Beast back when its business model was listening kiosks in record stores. Software Development Laboratories changed its name twice, first to Relational Software, Inc. then to Oracle — a brand that has proven extensible enough to go from relational databases to a dizzying array of software, hardware and services.

Buoyed by these precedents and convinced that a new brand was a necessary pre-requisite for our longer-term ambitions, we embarked on the months of planning and preparation that went into this week’s unveiling of Hightail.

One of our main goals was to select a name that would stand out against the preponderance of descriptive names in our space. The words cloud, box, share, and sync were banned as clichés. We also didn’t want a name that was a made-up word – a serious challenge given how many domains and trademarks are registered. Choosing the right name can be an imprecise art, but the one thing we were certain of was that it is better to be bold and unique than boring and forgettable.

Not everyone will like it but Hightail is certainly a memorable name that encompasses both our broad suite of current capabilities as well as our future innovations. It feels intuitive and fast, like it’s going places. Our new visual identity with its elegant design and adventurous color palette also sets us apart from the competition.

Ultimately a great brand is never the result of a name or logo, which are more like a promise that must be kept by the product or service the brand represents. The new Hightail user experience that will start to roll out in the coming days and weeks lives up to that brand promise. It includes a complete refresh of every screen across our web, desktop and mobile apps. In the coming months you’ll notice that we’ve rethought every experience across every product across every platform. This new experience reflects our commitment to always improve and innovate our products to solve the needs of our end users and enterprise customers.

As we continue to deliver great products and user experiences, the name Hightail will cease to be a mere word and become a strong brand. This video expresses our vision for what that brand will be. With our new name finally launched to the world, it’s now time to stop thinking about branding and start shaping a new one.


  1. Well, I want to be supportive because I use your service. Perhaps you’re planning on rolling out other products that have to do with speed… but to me, “hightail” is specific to running away fast, and I don’t think that applies to what your service now is. It’s more about handling big files… so a size-specific name would make more sense to me. At a minimum, I suggest a rethink of the H-logo. Everyone in my office thought it most looked like a stop-sign… which clearly does not embody the brand.
    Just my two cents. Good luck with the transition — I do like your service, regarde less of your name/logo choices. :)

  2. YouSendIt said everything I needed to know. Hightail is a meaningless word to me and, I suspect, to everyone outside of North America. I very much appreciate the service you offer, but if I were you I’d re-think the name!

  3. According to Merriam-Webster: to move at full speed or rapidly often in making a retreat — usually used with it …
    Which is not what you intended but is what my mind questioned when I first saw your planned change… Why would you not know the definition of a word before using it in an “opposite” function?

  4. It takes courage and sacrifice to change your identity. It takes time and it takes repetition for it to stick. My number one advice to companies that rebrand: “Don’t listen to detractors”. I have already said to a colleague “I will hightail it over to you this morning”.

  5. I’m afraid I agree with Zoe. There is much to be said in this world of over-complexity for something that is simple and telegraphic. Yousendit was that. It perfectly embodied what the service is, how it works, and was easy to describe to people. Hightail has no intrinsic meaning (esp in non-US cultures that do not have the colloquial ‘hightailing it out of here’). Similar to Zoe, i like the service and use it a lot, but the branding I think is a major step in the wrong direction….

  6. Nothing that I read above changes my mind about the name change. I don’t like it! From a marketing stand point it conveys the wrong message in every way. Seriously bad idea. I really like what your services. I have a paid subscription and love what it gives me the ability to do. When I think about the sending a file to a client and telling them they have to register with Hightail I get embarrassed.

  7. While the examples you site of name changes that we have all come to know and respect: E-Bay, Pandora, etc.have become household names, the name You Send It is brilliant. It accurately describes what your service does. And the airplane logo denotes fast service. In marketing, there is no better way to name a product than to have it’s name describe what it is or does. Sorry, but in my opinion, you are making a mistake. If it ain’t broke, don’t fix it.

  8. Nice video, it really communicated the ease at which people in the design profession can work together using your product. I live in the Bluegrass horse country so the name Hightail reminds me of a horse’s tail flying high as it runs through the wind.

  9. The only problem I and associates ever had with YouSendIt was that it’s slower to type on a keyboard than yousendit because of the interior capitalization. Other than that, it fulfilled a key role of branding – it told everyone exactly what it was all about, what service was offered, what it did. And that’s extremely useful. And in the process you developed a brand name that was catchy, useful, intuitive, and we all know that such brand names are not easy to come by; they’re the product of years of promotion and often vast financial investment. To throw away a brand and start over again isn’t always the smartest move. I understand you may be antsy-pantsy to have a brand name that can encompass much more than FTP, but I believe strongly that in creating a new brand name for a larger area of activity, you shouldn’t destroy something that has worked so well and is worth so much. Why start over again – with a name that means little and says nothing – and destroy what works?

  10. A name change is a big, bold move especially when you’ve built some brand equity. It’s also a huge process if your goal is to gain internal consensus that it’s the right thing to do and what the new name should be. Between confused and potentially even alienated clients and meeting upon (brainstorm) meeting, there’s a lot of work to be done. So kudos to you Hightail for making the move, then doubly so for taking the time to explain your rational in an inspired and inspiring way to the rest of us. I look forward to seeing what this new future brings for you.

  11. I agree with Zoe. Hightail to me means running **away** fast, usually by a crook or bad person. And your logo is OK but nothing to write home about. I wish I could be more positive about all of this because I love your service!

  12. I am a fairly long timer user of yousendit (a couple of years)
    and I agree with the other poster
    Hightail is not a positive term
    usually it does infer to run away quickly, usually because of some problem
    this name is not a positive change to be associated with
    not sure why “rebranding” to a somewhat negative term is occuring
    I for one have yousendit associated with my company in my communication to clients and links on my website
    I really am not sure I will continue using the service with the new term, I do not feel positive about the name change. Did you consider this with clients and focus groups? Is it too late to stop this name change?
    Just a strong suggestion from a long time satisfied user, you risk customer retention.

  13. Zoe … at this stage of the brand conversion a “rethink” of the logo is ridiculous. Come on. Unless Hightail (aka YouSendIt) asked the niece-of-the-janitor-who-likes-to-draw to do the brand conversion for free, a great deal of research and thought, not to mention blood, sweat, and tears went into this makeover. That said … I didn’t relate to the name at first, but it is growing on me. It is more interesting and has a broader scope than YouSendIt. I’m liking it. And, it’s a nice change to tell a client we are sending files via Hightail instead of the YouSendIt.

  14. Did you have to change the company brand – maybe for legal reasons or because you got bought out – or was this a choice? My staff and I have been using YouSendIt for the past 5+ years. We used to say, “Shoot it to me via YSI.” Now we’re stumbling with trying to remember HighTail, and we end up saying, “Shoot it to me on that thing — you know, ah Highbrow — er, you know, what used to be YouSendIt.” Some staffers, not remembering the new name, are using DropBox instead now. We all miss the paper airplane icon. The new logo do NOT depict movement. The H looks capped off, held back, restricted. Sorry guys, but when one develops a good relationship with a brand it’s very hard to let it go, especially for a new name that doesn’t roll off the tongue and a logo that is bland-at-best. I miss my YSI.

  15. I also wish you the best with this branding transition. But like Zoe commented above, “hightail” seems an odd choice for the service you provide. Hightail means to run away scared, scurry, or flee the scene. For english speakers, it’s most closely associated with frightened animals, embarrassed mischief makers, and petty criminals. And the “H” logo does look like a stop sign.

    Your examples of successful name changes were great, and I was hoping the video would hint to your plans for the future and why YouSendIt was holding you back, but it only seemed to show a team using what might as well be YouSendIt with a different skin. It’s possible I missed something, I haven’t had my 2nd cup yet ;)

    I like your service, and I won’t stop using it because of an awkward name or logo. So, keep up the excellent work behind the scenes, and good luck with changing the english speaking world’s perception of the word Hightail!

  16. Well… your services are excellent, and you may have a point in saying that cloud, box, share, and sync are clichés… but at least they are not evoking na image of a lifted tail. o.O
    Come on, was there no one, not one single soul, in all your naming meetings that brought up the possibility that people won´t like to say “I´m using Hightail”… or “I have Hightail” , for describing having an account… or even worse… “I´ll put it in my Hightail”.
    You had an excellent name before… and whatever wasn´t working that led you to think you had to reform your company, certainly wasn´t the name. Because you provide a much needed service, I really hope that you company succeeds despite this silly name.
    It would be a shame to see Yousendit leave the web with it´s tail between it´s legs. :(

  17. Well you can have all the meetings and referral’s to other moniker’s that have changed brand names you like but unfortunately you young cat’s have dangerously gone off-Track with your move.

    As a long time YouSendit pro user I was perfectly happy with your last Mac issue of the app but you’ve completely destroyed the Mac-Like GUI
    and blitzed the client list addresses in the process..(where is my address book?) Now it resembles some sort of traffic sign done on Vista in the dark crevices of the Windows world, definitely not for Mac users.

    I can tell you without question that you’ve turned off 97% of your music community users in Nashville all of whom were Pro users, YouSendit was our industry file sharing standard. “Was” our standard.

    You’ve really taken nine steps backwards and done yourselves a dis-service here jumping the gun without proper market / user research. I canceled my membership immediately.

  18. Concur with some of comment by Zoe. At first brush, caused me to think of ‘hightailing it’; as in, running away from something and I pictured the white-tail deer we have in East Texas. So, would like to see that deer’s tail incorporated into logo! :) Do greatly appreciate your service!

  19. Name changes are tough because everyone has an opinion, and I guess it’s natural to express them even after the name change is done.
    But now the name is changed, so go with it! I love the commentary and approach, and I love the name too. Hightail does sound like running away fast, but that’s not necessarily negative, and it does suggest other attributes – birds flying, moving fast, lofty ideals…You may change some people’s connotation of Hightail over time, the way Pandora did. Good luck!

  20. OK, fine. But I went and looked at the plans offered under the new name, and am completely dismayed to see that the “pro” plan that was perfectly suitable for my modest needs has changed dramatically – most notably by an enormous increase in price. Like, triple. What’s that about? Will you still offer a low-cost step above the free plan, like what I have now? At renewal, is my old Pro plan going to automatically change to the new “Pro” plan?

  21. I am a firm believer that a firm’s name should communicate the product or service, leave no guesswork. Hightail lacks content; it is your spirit for innovation, but communicates nothing about your product. Perhaps you should return to the drawing board, and I agree, the logo does not hit the mark either. You will forever have to include the tagline of formerly YOUSENDIT.

  22. Why???? Brand managers and graphic designers must do their jobs but just because they can, doesn’t mean they should. The brand was far better embodied as a paper airplane than a goal post, high hurdle, halt, block-on-block, inside a heptagon. Will the strength of your utility overcome this mis-step? I hope so. Wise up. Lines have meanings.

  23. You send it… Hightail…Whatever… it’s just a matter of shifting to a new brand, just make sure we remember!…You know, being literal in the description of a brand, sometimes helps people who don’t use you as often in the toma. good luck.

  24. Dear Sirs.
    Me and my company fellows were sursprised when Yousendit decide to change his brand name to Hightail.
    As english is not our mother tonge, we had a long discussion on what does Hightail means. We had to look after it in dictionaries because for us in not a common word. For a non english language user has no meaning, then is very hard to remember it and very hard (almost impossible) to pronounce it.
    Besides technical features of your services, people do not like products wich can not even pronounce.
    For people with a basic knowledge of english Yousendit has a meaning.
    Although the word Kodak itself has no meaning, is easy to pronounce in any language, then you will easy rememer it.
    How do a spanish mother tonge user pronounce Hightail? And a chineese or someone who speaks arab or afrikaans?
    Did you ever check the brand name with international users?

    Best regards.

    Pablo Badilla
    User of Yousendit from Chile

  25. Thanks for giving a background on your branding. It’s always interesting to gain insight into the brainstorming of a brand – especially a rebranded product. I understand Zoe’s comments – that the meaning of the brand to her is all about size. I like that the brand took a different path – to reach beyond just the product features, and after all, there are plenty of cloud products available since yousendit was conceived. I like the idea of ‘moving fast’ – as the owner of the account – that’s my main goal. The product is effortless and smooth – I have total peace of mind when relying on it to get my files where they need to go.

  26. I really like your service, and my clients all gain the benefit of my ability to handle large files for them easily. That said, the old name (yousendit) was fairly descriptive about the service and worked to portray what it was you were providing and enabling.

    Unfortunately, “Hightail” to me does not have an associative meaning to what it is that your firm provides. It almost infers a rapid escape from some danger or threat (as in “we better hightail it out of here…”).

    Shakespeare perhaps said it best – “What’s in a name? That which we call a rose by any other name would smell as sweet.” So I and others will get used to this new name, as long as the product and service remains “sweet” & excellent.

    I am suspecting that you (and/or the consultant you engaged for rebranding) were hoping that the name change would evoke praise instead of an expression of resigned acceptance or endurance by clients.

    Not to worry, you’re not fleeing a bad reputation (like AIG that had to hide from its name for a period of time by calling itself Chartis); you’re simply embarking on what you (and we your cleints) hope will be bigger and better things to come from Hightail.

    If the service maintains its excellent and you provide other advantages and improvements in the future; 6 months from now, the new name will subside into part of our normal lexicon rather than the rebranding being a topic of discussion on its own merits. I hope for and wish you all the best!

  27. Well as you informed me that you rename not only name but size and speed also of this files transiction service so for me you its rename to hightail because word high shows a big data and speedy transiction of files and tail shows that you connect to all over the world in one place as its all like your own tail means a good communication service of files transiction and its really look different to others Hightail also easy to memories and to discuss with our relatives that i sent something from hightail creat a nice understanding .
    thank you hightail

  28. Long time user of yousendit although admittedly less so in recent months. I applaud your rebranding efforts and appreciated the back story in this blog article and the one aligning with NASA in the ’60s.

    The word mark is bold and the colors are indeed vibrant. The only suggestion is to omit the orange bar over the H because the negative shape introduced via this white space is a T.

    My brain translates this information: HIGHTAIL = THIGHTAIL

    This is admittedly silly and absurd for me to even consider, but my brain is seeking out the a-ha moment/punch line that’s akin to the FedEx logo—once you see the arrow in the negative space, you can’t un-see it.

    Food for thought…

  29. I share you pain – we have done the same recently changing our name from GenieMobile to GenieConnect reflecting the shift in our industry from just mobile event apps to event participation solutions across Mobile, Tablet & Desktop web and creating a Multi screen solution that people expect these days – al la Amazon and Ebay, facebook and Linkedin. We are working hard to build the brand back up to the level it used to be and recover some of our natural search positions for some of the key terms. Its a fun challenge I have to say – but we will get there.

    Good luck



  30. Yes, it feels fast and I understand the imperative not to go for something overly restrictive. But unfortunately “hightail” comes with baggage. It’s so specifically tied to the phrase “hightail it out of here,” which connotes mischief, perhaps even crime. The fellow subscribers I’ve talked to agree it is a poor choice that causes us rethink our relationship with the company, and not in the good way you were hoping we would.

    While you nicely sum up the challenges involved in picking a name, your defense of the particular solution you chose (and it sounds defensive – “not everyone will like it, but”) is quite ambivalent – at least we aren’t forgettable seems to be the main attribute.

    I’m sure the annoying name will fade, as you say, and the products and services will become what I associate with it. I do hope so. YouSendIt was a godsend when it launched, and I have only been disappointed a few times, basically due to lack of clear communication during outages. Good luck.

  31. I like it! Regardless of file size, I use this service when I need to get something out fast. And thank you for not creating a logo that even remotely looks like it has a tail. Plus, who doesn’t want their company name to be a verb? Well done!

  32. Hightail: to get out fast – That is exactly what the service does. Gets my large files out fast and I don’t have to look back. Nice job! Love the service, love the new name. This will be much easier to explain my files will be coming to you from Hightail vs Yousendit, uh? u send what? Well Done!

  33. Most of my professional career has been focused on business identity (logo) development and branding. With awards and recognition in over 35 years of Agency work as a Creative Director, I certainly can appreciate your wanting to try an build something new with the company’s image. My response however, is that the original “YouSendIt” was profoundly accurate and complete. Even the glyph of the paper airplane was right-on target. I also agree with most all of Zoe’s comments – multi-colored “stops signs” ? Guess time will tell how successful this effort will be.

  34. Everybody agrees, name changes are difficult. The trick is to keep your product and your service a the highest level. I’ll keep using your service as long as it continues to work well. I’ll get used to the name.

  35. This is going to be tough for you guys:
    A. People don’t like change.
    B. The logo seems to represent the opposite of what your service does.
    C. The name has a different connotation than what you intend and you will have to change people’s associations with that word.

    I am a long-time user and will continue to use it until it no longer serves my needs. But I am reluctant to send clients to a site called “Hightail.” In addition to the “running away” definition, it also brings to mind online hook-up/porn sites. You have a long road ahead of you.

  36. Reading the feedback on this blog has been quite insightful. I love that someone has thought that hard about it and actually concurred the logo looks like a stop sign. That person should be on a design team. And that Hightail is a negative connotation. Way too much thought in my opinion.
    Yousendit was a great name, Hightail is a pretty crap name but its just a name, if it doesn’t affect your business i am sure people will get used to it. Good Luck with it all I think the biggest problem with it will be attracting new customers as it has no reference to your product. Hopefully your SEO and website developer is better than your name changer at his job though and used yousendit in your keywords list!

  37. I am a commercial model and only used YSI to view comp photos for approvals through my photographer. Having the ability to view my files online is a huge bonus however, the name change is quite confusing.
    I hunt white tail deer in the fall and my lodge is named hightail. The name indicates a fast chase and the white tail wagging in the tall grass. I’m interested to know if the decision maker hunts and did not think about how unrelated the name is? The name change has no real conceptual meaning to the business. It’s rather insulting to the service and consumer confidence in management. If I had no idea about YSI, I would turn sideways towards a company with a name that made more sense. Sounds like they hired a guy making too much money sitting in a deer blind.

  38. Interesting comments. I agree with the new name’s limitations re: pririent connotations or re: not really capturing what it does. I just hope I remember it. I enjoy the service and sold many on the concept of “you want it received without hassle” then use “you send it” .

    Maybe make “you send it” a part of the new group name “hightail”
    Good Luck

  39. My first impression was ‘meh… but then I realized it has an endearing memory as a word my grandfather would use. Not always in a “retreating” reference – just to move quickly. So I thought of it as an old fashioned word – one hardly used any more – but being revived for the 21st century lifestyle.
    Sort of like hunkie-dorie. I remember a friend trying her best to revive that word about 25 years ago. I’m not sure that worked out well for her (or the word) but social media had yet to hightail it anywhere.
    Good luck – I like it. I think it’s hunkie-dorie.

  40. Different name,great services!
    My monthly service went up only $0.54 cents,so what’s all the complaining about increase is plan costs?
    Really people….you spend more than that on a cup of coffee!
    Hightail,keep up the great work!

  41. Desirable, global & bold. Its a gutsy move providing a stable springboard helping build a sustainable, future-focused brand. Embrace the change!

  42. Hinkie-dorie it is. Think of how it works so well in daily work conversations: “I will Hightail it over to you this morning.”, “Could you Hightail it to me?”, “I gonna Hightail it outa here.” Kudos.

  43. I am always curious when a successful company decides to do a major brand identity changes. From a Brand Strategist’s perspective, I would need to know your future business ambitions and whether there where any negative reactions to the existing brand before fully evaluate your re-branding efforts but here are my initial thoughts:

    Educating and engaging 43 million users is quite the undertaking. My first reaction to the name itself was negative for several reasons: it’s not a term known globally, Hightail can connote ‘get the heck out of here’ as if something was wrong, the spelling isn’t evident from the pronunciation (Hitell, Hitale, hightelll, hightale) and as a specific word, it doesn’t convey ‘file collaboration’ to me.

    The visual branding is nice but I think you could have leveraged the success of your previous identity to make it easier for existing customers to make the transition. Why not at least keep the same color palette? The previous green and blue icon has more visual interest, conveys movement, and works great on it’s own. I would have made every effort to keep a part of that. The line above the H in the new logo seems bulky, static and uninteresting. It also seems trendier than the old icon, which will date the company to this time period.

    The video created didn’t keep my interest; it seemed slow and too literal. I felt like it was a training video on how to use a product. Having experience as a video producer, I would have done something fast-paced, with lots of motion and activity to convey speed and collaboration. It could have been shorter too.

    If you can fulfill your brand promises through your products and services, make strategic brand decisions, put tremendous effort and enough money into your re-branding efforts, I do think you can be successful. But I would watch what your competitors are doing during this time to counter act any of their efforts to gain market share from this. If customers are forced to make a change, it can trigger a reaction to compare other options they might not have considered otherwise.

    As a YouSendIt customer, I haven’t received any notification yet so I’ll be interested in seeing what is to come. I look forward to evaluating the success of your rebranding at a future date.

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