Two very different products. The same underlying problem.
StreetEasy had a real relationship with its city. New Yorkers genuinely looked forward to the subway ads. The voice was sharp, irreverent, unmistakably local. But that brand identity stopped at the product door. Inside the app, the pages felt generic, inconsistent, and technically dated without content strategy to hold them together. Users had the tools, they just couldn't find them, understand them, or trust them enough to use them.
Out East was the opposite problem: a completely blank canvas. The StreetEasy founders saw an opportunity to take the Hamptons' outdated, barely usable MLS and build something actually worthy of its market. Just me and one UX designer built out brand naming and the full site from navigation labels to OOH campaigns.