You got a bunch of people about to turn orange

I’ve always championed our company’s rebrand using this audacious analogy: Hightail is like NASA in the 1960s. Our users are the astronauts taking giant leaps of creativity, while we’re the geeks at Mission Control calculating air-to-fuel ratios and parabolic trajectories to ensure Neil and Buzz get where they’re going, then come home safely to enjoy tickertape parades and punching conspiracy theorists in the face.

Space exploration became an internal theme of the new Hightail brand that even extended to the names of the various project teams working across all our products and services: Centauri, Orion, Polaris, Pulsar — everyone at Hightail is looking to the stars. The design team’s mission was to create a visual identity that matched these lofty ambitions.

The Hightail Wordmark
The Hightail Wordmark: while inspired by a masterful typeface from Hoefler & Frere-Jones, each letter was redrawn to bring a custom feel to the Hightail experience.

The Wordmark

The text-only lockup of our name had to be bold and instantly recognizable. As I worked through different versions, I kept asking myself: would this work on the side of a space shuttle? Though simplicity was the main aim, I also wanted to give the wordmark something extra. The horizontal bar over the H adds a playfulness that subtly conveys the idea of doing more and that’s what Hightail is all about.

The Hightop

The Hightail wordmark is an introductory handshake that appears on our marketing and sales material, in press articles and on our corporate website. But we also wanted another mark for our users — something more personal, a sign that you’re among friends.

The Hightop in the spectrum of Hightail colors

That mark is the Hightop and it represents how we want people to feel when they use Hightail. It’s a design you might see on an astronaut’s mission patch or an Eagle Scout badge, a mark that symbolizes the success and accomplishment of completing the task at hand, something that lets you know you’re part of a team.

Circles are lazy

These days a major function of any logo is to be the app icon on a user’s phone or tablet. Rather than be dictated by the tile format of mobile devices, I wanted the Hightop to have its own frame. But I refused to use a circle, which too often feels like the lazy option, a comfortable crutch used as an easy fix for any lame design.

All circles are the same so it’s almost impossible to create one that stands out. I wanted something different, a shape that would speak to our brand values of exploration and movement, a frame that was balanced and geometric but also dynamic and original.

Odd number-sided shapes are perfect thanks to a flat base that grounds the shape and a point at the top that moves your eye up and out. Triangles are boring, pentagons are too militaristic and nonagons don’t reduce well, which made the heptagon an easy decision.

Besides, I love me some Akira Kurosawa, baseball, the ancient Egyptians and Sunny Day Real Estate, so a heptagon made perfect sense.

The beginning

I’m proud of the new Hightail identity and of the amazing work done by the whole team here. The primary mission was to deliver a strong, unique brand and we’ve achieved that with our fantastic wordmark and logo. But the real work starts here. Now we have to instill our new brand with life and make it mean something to people.


  1. It’s nicely done, but I can’t help thinking it’s a lot more generic than the old one. The paper plane communicated something, the new logo is just kinda pretty. Although I do really like the new name.

  2. Sorry to be negative but I was very disappointed with the new logo and color orange. I think it would have been a great move to at least keep the color scheme from UsendIt. That was a logo that will be remembered forever. Good luck to the company!

  3. hmmm. i am not sure about this design. it looks like industry, very heavy and masculine, like you are digging coal in sibir, producing some heavy metal products or digging highway under the earth…

  4. Check your english……. day 1?

    The special Hightail edition

    From our new name and logo to the evolving product experience, we explore what it means be Hightail.

  5. Ok, all good to compare your creativity and service to the world to the space race. Cyberland is to, as Buzz Lightyear says. “Infinity and Beyond!” I find it fascinating, I a customer and paying client, complainted about the Screaming Color User Interface, and had no acknowledgement. You might be more successful if your attention is directed to how the User feels/thinks/experiences the service. Don’t you want product adoption more than kudos for cleverness?

  6. I am a graphic designer and subscribe to Hightail (YouSendIt).

    The design (although the justification is over intellectualized) is acceptable but I cannot come to grips with black & orange without thinking of Halloween. My personal preference in a two color logo is green/black or blue/black. Research shows that the cooler colors are the most confidence inspiring. However, I am “old school” when it comes to color theory…

  7. I think your rebranding exercise is going to end up being more important to the people who went through it than your customers. The video of your leadership team (“executives”) with hip sounding job titles came across as flat and uninspired, overscripted, not authentic. The video, and your big rollout campaign, go at great lengths to discuss how your team approached this, how your team thought about, the process your team went through — that’s the takeaway from your rebranding campaign, not what’s in it for the customer. It’s about “we want the company to go here” or “we want the flexibility to do something unimagined”, but there’s nothing about what’s the benefit for me your customer. I detect a strong infusion of millennial “me-ness” in this. You are all very proud of your work, and I’m sure it’s fine for a segment of your market, there’s just no “me”, your customer, in it. Good luck!

  8. I still have no idea why you (all) had to make a change? For me, as a hardened design consultant, I bought into your (all) service because of the wit and simplicity (and timelessness)of the original paper plane image. As an IDEA it immediately conveyed the concept of the movement of information in an identifiable and accessible way – it was a fantastic design metaphor and I found myself ‘envying’ the outcome (as a conclusion I would have been happy to achieve myself) and identifying with it ‘in the same breath’.

    For myself, it has reminded me in a fairly dramatic way how much an identity impacts on personal perception and engagement. It’s fair to say that I am now ‘at sea’ – I understand all the problems and complexities but I don’t identify with the new identity one bit (emotionally) which may well have an impact on my decision making re. your type of services in the future…

    I sincerely hope there was some really important reason for this change – like a fundamental worldwide copyright issue – and that your customers ‘warm’ to the new identity.

  9. You guys sadly followed a trend — condensed typography, hipster emblem shape for the mark.

    Try designing something that isn’t ephemeral.

  10. The circle shape might not have much variation but it is definitely not a lazy option for a logo. Many iconic brands use the circle shape in their logo design and are able to distinguish themselves from others that also use the circle. For example, Target, BMW, and even NASA. It’s what the designer chooses to do within the confines of the common shape to create something unique and symbolic. Which, to me, seems more like accepting a challenge rather than taking the lazy route.

  11. Really don’t like the new name or logo.

    I am a graphic designer and work with marketing and communication professionals. We are all BAFFLED by YouSendIt’s decision to dramatically re-brand itself. Around our office and within our larger organization and outside consultants/colleagues, “YouSendIt” had just started to become a solid part of our lexicon, sort of like “xerox this” or “FedEx it” — we had started to say, “I’ll YouSendIt to you”, that sort of thing — and people understood immediately what we meant. Even the technophobes in our organization (older people, upper management, etc.) had become comfortable with “YouSendIt” not just as a name but also as something they could easily use. People even liked the paper airplane logo as it was welcoming, friendly and somewhat whimsical.

    And now you have tossed it all out, changing your name to the non-intuitive “Hightail” with a very authoritative and forceful logo. We suppose you must have a good reason for this big change, but we are all thinking this is going to be a disaster for your company a la Netflix and New Coke.

  12. What is the point of the change? I don ‘t see major innovations that I will use on top of the excellent YSI service which is in constant use in my business. Please tell me why you needed to make this move.

    I frequently encourage people to try out YSI, should I now stop doing tht?

  13. One further comment. I would recommend others to use Yousendit. Can’t see myself saying why not try Hightailing it…… enter the Lone Ranger and Tonto LOL

  14. Why? YouSendIt clearly communicates what your service does, or did. Hightail? Not so much. I remember from the old westerns “hightail it” meant to hurry, as in a horse’s tail being held high when it ran at top speed. (They also raise their tails for another less elegant bodily function!)
    So. what will be so new, necessitating a new name (oops! BRAND! sorry!)
    I don’t like the new name because it decreases recognition of your core function. That said, I plan to stick around and I do hope for your continued success. Just don’t become complicated. The main reason I prefer YouSendIt has always been its simplicity and ease of use. Just don’t change that, ok?

  15. As a graphic designer, I am also struggling to come to grips with the new name and logo. Like all things, we resist change, especially when the old seemed better than the new. I think the rationale about space is not related, unless you actually do intend to send stuff to mars !!! But enough negativity, like steve jobs said, ” people dont know what they want until I show it to them” Good luck.

  16. Ditto Barb, Sally Aberton, Skip Moskey, Neil Lumby, Sarah, Big See and Brian. I’ve read all the Hightail emails and newsletters. I’m still trying to figure out what this means to me, the customer. What I do know: when I send a file to a client, I’ll email them and say “I’ve uploaded the file to YouSendit (now know as Hightail)”

  17. The layout has been simplified and cleaned, the color combination breaks with the yousendit style, I suppose that was one of the goals, it “force” people to forget about the previous layout… still I miss the blue and green, those colors make me feel good, now there is a big grey block, simple but oppressive… anyway I suppose is a question of time get used to it… in my opinion the biggest lost is the “yousendit” name, for me as spanish make sense a service like this to have this name… but “hightail” ? cola alta? I still try to figurate what does it means !! XD A big marketing effort will be needed to make customers and public relate Hightail with the service provided.

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