Rebranding Upwork
(in 6 weeks!)

Upwork had plans to reintroduce its brand while introducing a new industry category—the world’s work marketplace. The company wanted the entire visitor site rebranded with new messaging guidelines and design components. In 6 weeks. With very little lead-in time.

In came content design to take a complex ask and manage what was feasible. After a few deep breaths, we jumped in to figure out: What can we realistically commit to? And how do we make sure such a fast-moving rebrand doesn't overlook critical usability elements?

First we needed to communicate to the teams driving the project the full scope of what they were asking.

I reviewed all of our pages to identify:
- the focus of the page, main call to action, and UI elements
- responsibilities of content design vs. marketing copywriters
- key stakeholders and dependencies
- estimated level of effort
- notes for other potential changes (in case we had time along the way)

We set up 1-week sprints which included
- frequent check-ins
- planning sessions with stakeholders
- management of copywriters
- writing or rewriting content
- group content critiques with the marketing team
- sign off meetings with the VP of marketing for every page
- legal review
- design sprints where I helped integrate content changes into the new look, sometimes needing to troubleshoot and rewrite on the fly

The writing and critique process helped time box the work, keeping us focused on priorities (that part was crucial—it's easy to get distracted by what if's when reviewing so much legacy content!).

Stakeholder management was tricky at times, with everyone considering different aspects of their pages as unchangeable, or having different understandings of the aim of the rebrand. We tried to include them in as many decisions as we could, but our time and attention was limited, so there were times we had to make judgment calls on considering feedback as an opinion or suggestion rather than a mandate.

Still, I was happy with how I represented content design to teams of all flavors. And I learned a lot about common interests and conflicts of priority across the company (some necessary, some not so much).

A few of our high-converting, high-traffic acquisitions pages were critical to overall revenue and business growth, and with some early trial runs of the redesign of these pages we saw a significant drop in registrations and clients who posted their first job.

A couple weeks before rebrand launch, I joined a small growth team to run rapid tests of micro iterations on these pages, followed by reviews of the findings with the analytics team a few times a week. We made adjustments on color, spacing, headline and subhead copy variations, and more, all as a team, and all with time against us.

By the time we launched (deep breath...) key metrics on these pages were flat (...big sigh of relief), and the pages were ready for bigger ideas and optimizations post-launch.

Although we were successful in pulling off such a massive project, I would have wanted a bit more prep time and more of an opportunity to anticipate the impact of changes, either with user testing or additional growth experiments.

I appreciated times when I could improve more than just the minimum viable content. This wasn't a priority, but I find that high-profile projects are a good place to make a case for quality of life upgrades that sometimes go unnoticed by bigger business goals. ("We can always update the copy later" is often code for "This isn't worth our time"...)

I also put some extra effort into pages that didn't drive revenue but still had a place in the overall experience of the visitor site, like a 404 page which we made a little friendlier and more helpful, and a reviews page where we took a more humble approach and highlighted the value of client and freelancer relationships.

‍This was a crash course in a massive area of the product. It would later come in handy for other teams as I would get called in to consult on visitor site content

Many of my observations set the stage for follow-up growth experiments that I explored throughout the year. Ideas that I had wished we had time to address during rebrand ended up driving or contributing to significant impacts later down the line.

I also loved seeing people coming out of content critiques with a positive impression and understanding of content design. Those intangible improvements are important to celebrate, even when the road to get there is a little messy.