Pitching a Site Overhaul

At InsureMyTrip, I asked for the chance to rethink and redesign our high-traffic, e-commerce website. The website was outdated, not easy to update even for simple content changes, and lacked useful content and features like site search. Because it was ambitious, we called the project Super Redo.
 
The images below are from the presentation I made to senior management to pitch the project. I wanted the slides to be simple, with strong images to poke people attentive and little text so they would listen to my story rather than read the slides. I'll try to recreate a little of what I said back then beneath each slide.
  
 
This was the old and tired brand logo. I started with this because it represented a design state from which this project would attempt to shoulder the company forward.
 
 
Next up was Cassius Clay (he hadn't changed his name yet) towering over Sonny Liston in '65. Phantom punch or not, Clay/Ali was and is still considered to be the best heavyweight in history. He was the greatest.
 
We weren't aiming to make a better website or a good website; we wanted to make the greatest website. I don't know if we got to wear that crown after we were done, but we got where we got by aiming high.
 
 
To achieve something great, first be clear about the goals.
 
 
"Simple" is from John Maeda (and other folks, of course). "Enchanting" is from Guy Kawasaki. Great design makes complex things like insurance less complex. Great experiences end with people feeling happy. Yes, even experiences with insurance can leave people happy.
 
 
This project had several customers: the people who purchased travel insurance on our website, the companies who sold travel insurance through our website, and all the people in our company who used and supported the website. I wanted to make sure that what we built would improve things for all three groups.
 
WordPress is a relatively simple website administrative tool. It allows people to publish and do things, like we wanted our website to be for our internal users. It also was the most prolific publishing platform on the web, used by almost 25% of all websites. If we provided more value to our business partners, we could become that entrenched in the travel insurance web.
 
 
In any ask, talk about the benefits.
 
I believed that a great website would make the company more productive. I wanted the executive folks to understand the project as a good investment, from all the angles.
 
I've never surfed but my impression that there's a focus that comes from a person, a board, and a wave. The Otter Surfboards website is one of the cleanest and most focused sites I've seen, which speaks to its audience. The site enchants them (a bit) like the water.
 
This project was about so much of the website, not just the top layer. But, damnit, we were going to make that top layer speak to our audience and make them want to spend time on the site. We were making a siren. Without all the rocks and the crashing, of course.
 
That's the Tower Building, considered to be New York City's first skyscraper. At that time, tall buildings were built of stone and brick. The skinny lot at 50 Broadway wouldn't allow for many stories (and not much income) with a stone building. The owner asked architects what could be done, and none had any ideas except for Bradford Gilbert, an architect of railroad stations (including Canton Junction, for you people local to Boston). He had seen a lot of railroad bridges and it occurred to him to turn one on its end: To use steel.
 
People laughed at him. But it worked. And now we have skyscrapers.
 
I heard that story on one of my favorite podcasts, 99% Invisible, by Roman Mars. The story was told by Nate Dimeo.
 
I told this story in the presentation to forewarn folks that to get to great, to reach higher, we would need to change some frameworks and, perhaps, some of the materials. But we would make choices that allowed everyone to go higher.
 
How do you know if something's great? You measure it, of course. I had a goal of implementing a solid metrics program for the new website. During the project we updated from Urchin to Google Analytics and implemented ClickTale to watch our customers' behavior on the site.
 
We built an A/B/Multivariate testing framework into the site's new architecture. And we didn't just add site search, we added search with logging (obvious, I know) to learn from the words and phrases people searching for.
 
With better data comes better decisions. We didn't just want to improve the site, we wanted to improve how we improved the site after the project was done.
 
It looks a little funny to be talking about appliances in a proposal about an insurance website. I believed we could find a better way to help people find the right travel insurance for their trips by building a smarter, interactive solution. The above screenshot came from a website that did just that, for appliances: It helped you find the right part.
 
I can't go into the details of what I proposed for a travel insurance "assistive engine," because that information is InsureMyTrip's information.
 
Let's see: We needed boxing gloves and a lot of steel. What else?
 
First and most importantly, we needed a great team with the right skills. We didn't get everybody we needed, but we did get great people: Chris, Hristo, Eric, Debra, Jerry, Wayne, Alex, and some others. They all worked hard and they all did great work.
 
I knew that this would be a difficult project and that it would take some time. We'd need support during the difficult times. This project needed commitment from the team, the executives, and the organization.
 
I believe in collocation. I believe people do their best work in inspirational spaces. We did get our own room with windows and whiteboards. I also got the iconic Farrah Fawcett poster (and hung a toddler-sized Run DMC t-shirt over her bathing suit), for inspiration. We got to know each other, we had fun, and we built trust.
 
The actual project timeline, of course, looked nothing like this. And it went for 6 quarters, not 4. But considering we were a team of only 3 for the first 3 quarters, I consider the actual timeline a great accomplishment.
 
I included the above slide to let the executives know that we needed project planning.
 
I ended the presentation with a new version of our logo, created by Hristo Kanchev. It wasn't the final new logo. Hristo came up with something even better.
 
From the old logo on the first slide to a new logo, from the old website to the new website, we were reinventing things. I believe that is what good design and good work should do.
 
The new InsureMyTrip website launched fully in November, 2013 and resulted in a 15% increase in sales conversions (among other metric improvements). That felt pretty great.