After freelancing for 5 years, I had gotten to the point where I craved more stability, less headaches chasing down clients for money, the possibility of making money beyond the hours I was working, and health insurance. In other words, I was ready to take the plunge into full-time employment.

At the same time, It was a transitional moment in New York City, where the burgeoning tech start-up scene had begun to blossom, with Gilt representing perhaps the fastest growing, along with ZocDoc, Tumblr, Foursquare, and Etsy. Additionally, through a friend, I had heard Gilt was a great place to work, so I sent in my resume, had a few in-person interviews, and almost exactly one month later, I joined as the tenth member of the tech team, and around their 100th full-time employee overall.

Once I started, it became very clear that I was hired specifically to replace another member of the tech team, and one of the very first employees at Gilt—let's call him "John." Based on the internal chat logs, it seemed John had a long history of pushing back on the design team, often telling them that their mock-ups were unnecessarily complex and that he would ofte... Read more