We meet Gordon at the beginning of Season 2, who is Adam Braverman's uptight boss. Adam, struggling to come up with more ideas for new shoes, gets an idea from his sister, Sarah Braverman, and gives it to Gordon, who loves it. Eventually, Adam reveals that it was his sister who came up with the idea, not him. This lands Sarah a job as an intern at the company, much to Adam's dismay.
Sarah and Gordon meet, and they immediately hit it off while sharing their lunches at work. Adam watches the two as Sarah reveals family secrets to Gordon, angering Adam. Adam confronts Sarah, saying that Gordon is trouble and shouldn't be trusted. Sarah refuses to listen and accompanies Gordon to a shoe convention business trip, while simultaneously blowing off Mike, who she has been casually dating. This ends their relationship, giving her the freedom to see Gordon. Gordon and Sarah kiss in the parking lot, but Gordon fails to mention it during the next day and acts like it was nothing, upsetting Sarah.
Later, Gordon tells Sarah that she is completely wrong for him since he usually dates younger women, she has children, and they work together, but nevertheless, he can't stop thinking about her. Gordon assists Sarah with getting Amber Holt and Kelsey from a party, and they kiss at her house, starting their relationship.
Gordon and Sarah continue dating even though Adam still doesn't trust him. Gordon invites Sarah to accompany him on a business trip to LA, but she decides to not go. Soon, her shoe idea doesn't sell, and she and Gordon get drunk in a limo to get over it. They sleep together in the limo.
Episodes later, Gordon decides to sell the company, but doesn't tell Sarah. Adam finds out and confronts Gordon, saying not to come to their Thanksgiving dinner. Gordon comes anyways, and he and Adam get their anger out in a football game, where the secret about the company is spilled. This causes Sarah to break up with him, and Gordon is not heard from again.