Photo credit: Rita Chen
Challenge:
When the City of Chicago called about an opening on the new Riverwalk, I saw something nobody had asked me to look for. City Winery was already a beloved brand in Chicago, and it was anchored in one location. The Riverwalk was a chance to extend the brand's reach, attract a new audience, and plant a flag on one of the city's most exciting public spaces.
The catch: it was not my job. I had to build the case from scratch, sell it internally, and then execute it, on top of what I already owned.
What I Did:
After extensive research and rigorous financial projections, I built the business case and pitched the idea directly to our CEO. With his green light, I kicked into gear — managing everything from strategy to execution, including vendor selection, signage, marketing materials, and even furniture options.
I also navigated the city partnership closely, working with the City of Chicago to ensure the proposal was compelling, the terms were right, and the launch delivered.
The Result:
What started as a summer outpost is now a permanent fixture of the Chicago Riverwalk. It generated millions in additional revenue for City Winery and became one of the top revenue-generating locations in the brand's portfolio in its first season.
The success didn't only benefit City Winery. It contributed to the Riverwalk becoming one of Chicago's top attractions, a long-term partnership between the brand and the city that continues today.
As a surprise gift, the team named a table after me. The nameplate is gone now, since Riverwalk summers are not gentle on wood, but the story remains.
What This Means For My Clients:
The best opportunities are often the ones nobody handed you. This project happened because I was paying attention, connected the dots between what the city was building and what our brand needed, and was willing to do the work to make the case before anyone asked. That instinct, spotting the opportunity hiding in plain sight and building the strategy to capture it, is one of the things I bring to every client engagement.
Rita's Table — Chicago Riverwalk, City Winery. A surprise gift from the team. The nameplate didn't survive the Chicago summers, but the story did
Photo credit: Rita Chen
