Looking back on old design work is like cracking open a yearbook from 1994. You thought you did so well. The plaid shirt. The purple. The elements themselves were thoughtfully curated, but together they look jumbled. Insane. Recently I was possessed to go over some of Trippeo’s old work for inspiration, and nostalgia (I’m still riding this new year’s train of optimism and excitement). I thought you might like what I found. Or hate it; both are enjoyable.

Initial Launch Page

I made this in early 2014. I call this iteration “Trippeo rave edition.” I mean, my logic was sound. I wanted something that would get folks curious about the product and wanted it to stand out at the same time.

In retrospect, the colors were nuts but at the time they felt like the right call. It’s a good way to create backlinks right off the bat: bloggers love (and love to hate) design, and so having a stand-out one was a great way to generate buzz (and backlinks) right away.

Landing Page, V1

I worked with the amazing Benjamin Guedj and Jean-christophe Suzanne duo to come with a “stand out of the crowd crazy” landing page that really elevated the Trippeo brand. And as expected, they delivered. This landing page won us a bunch of awards and I still really like the design and visual elements, but as a SaaS product, we failed in conversions. We had a ton of curious signups from the design and web community, but the all crucial free to pro conversion ratio was low. We abandoned this page after just 3 months, but you can still view the live version here: http://v1.trippeo.com

Trippeo Swag

Trippeo Boarding Pass — SXSW 2015

Armed with shaky branding and uncertain tone, we charged towards our first conference. And no self-respecting company hits the expo floor without some very cool swag. There is a huge subset of attendees that need to be lured into earshot with the promise of free stuff. Boarding passes! Cool, subtle, easy to carry. And (to us), pleasingly clever. Too clever, as we discovered. Too subtle. A pass granted the carrier a free Lyft ride, and a coupon for Trippeo, but there was so much happening on the pass that most people thought it was just a very fancy bookmark. It also wasn’t very useful beyond the conference itself, which guarantees that recipients will leave that carefully planned swag behind in their room.

Trippeo Illustrations

This was around the time that we hired our first full-time designer. For CEOs that are design-minded, like myself, it can be hard to cede control. But Zac brought so much to the company that we loved, and that ultimately pushed us towards a more illustrative, adult style that echoes publications like the New Yorker. We still had a lot of opportunity to be fun and boundary-pushing, but this was a gentler approach that felt more in line with what our business offers and feels like. It’s not perfect, but it’s bold and considered. I appreciate that.

Trying to SaaS

Our current homepage tried to tie all of these weird, esoteric elements together. Trying to illustrate a complex brand essence, and communicate what that brand actually does… it’s really hard. Color to keep us fun, product shots to communicate our ease and sensibilities. This effort still felt a little too formal: a little too like the the rote (but instantly recognizable).

So, what now?

I think you can tell even from the way that the tone of this piece changes how much we’ve changed since our inception. Our design has been a driving force of our brands’ shape and essence. Finding new directions isn’t just a line item on our daily to-do lists: it’s something we sneakily spend time on when we’re supposed to be iterating our QA processes, or writing a press release. We came across our newest designer, Chris Dammeyer, by trolling Instagram for locals. His photography-focused projects embody the fun and quirkiness. If our design denotes our brand’s personality… we want to be quirky and fun, but also elegant, and refined.

You can see how this is a hard balance to hit every time. Keeping with the allegorical theme, I think I only hit this in terms of my own personality upon entering my thirties. And sometimes I regress.

But we’re working on it. This month in particular, we have a ton of releases that will inform the direction of our product. We have a lot of growing to do yet and you can check it all out on trippeo.com later this month. Stay tuned.