After Stu Hoffman's, the VP Creative Director of Chicago's Rothman, Greene & Mohr Advertising, campaign for Arc Mobile is rejected he is found dead in his office and the Group Creative Director Tony Mink wastes no time in appointing Art Director Mason McGuire to Stu's old job which causes a conflict with his friend and work partner copywriter Conner. Meanwhile, new copywriter Sarah Krajicek-Hunter, who found Stu dead on her first day, begs for her old job back at DDB after a disastrous presentation but they don't want her back.
After Conner inadvertently uses a copy-line designed by another copywriter for the Arc Mobile campaign, Mason has to find a way to change the focus groups liking of the line so that the line is killed before the original copywriter finds out and sues the firm. Meanwhile, Sarah adds to Mason's stress by canvassing for a window office like she was promised in her interview and disliking Mason's choice of partner for her now that Stu is gone. Elsewhere, Conner eventually persuades Mason to take Stu's old office.
Mason puts himself and his job on the line when he promises the CEO that his new partner will bring his team success. Things couldn't be any worse for Mason, he is unaware that Sarah is not only frustrated with her job but is also entertaining other job offers. And Conner runs into an old flame.
Mason misses the mark when he surveys his atypical daughter about trends with typical teens. It's up to Conner to save the day when Mason keeps digging himself into deeper trouble with the client by making promises he may not be able to keep. When Sarah's romantic life is called into question, Hector and Tom complete for the opportunity to clear up the matter.
Production comes to a grinding halt when a client decides to rethink the campaign. Conner puts jobs on the line when he chooses to continue production with overconfidence in his ability to convince the client to move forward with the commercial. To celebrate her birthday, Sarah tries to go back to the way things were when she attempts to reconcile with her ex-husband. Already worried about losing his job, Tony receives some unexpected news about his daughter which sends him reeling.
Mason convinces Tony to allow his group to create a campaign for the potential Chicago Olympics. With the entire team assigned to the project, Mason and Erin have the opportunity to get away for the weekend, leaving Conner at the helm. Sarah and her new partner clash when their two very different lifestyles collide, making them both wonder what they each truly want in life.
Mason and Conner both face financial upset revolving around work, but for very different reasons. Mason struggles with the raise he never got an unaware Erin hires a contractor for some home renovations while Conner must repay the company after some questionable expense reports come under review. Sarah is at the end of her rope without a partner while she continues to work on the bane of her existence: hair care. Suddenly she finds herself competing with her co-workers' campaigns and wonders if she can turn her bad luck string around.
Competition gets fierce for Mason and his team when they try to win a new energy drink account. But things become complicated when he learns the client is having a beyond-professional relationship with someone on the team. Sarah decides to try a dating service to help her find a perfect mate, but may end up regretting it all when she allows Conner to help her fill out her profile. Erin decides to pop in for a visit when she thinks that Mason may have interests outside of their marriage.
Conner finds himself in a jam when he vouches for his former partner who is unable to come through on a freelance deal. While trying to nap a spotlight beer account, Sarah draws attention from Simon, who decides to bring his group into the race. Once again upsetting the balance at home, Mason learns a valuable lesson when he meddles in Haley's love life.
Tony loses all control of his anger when Simon and his group jump into the competition for the beer account that Sarah worked so hard to bring to the company, which leaves her feeling torn between the two teams. While Conner works on the bum assignment of making a birthday video for Tony, he unwittingly discovers an interesting office secret.
Mason questions his career choice when he receives an unsatisfactory job review. In order to deal with the team's neuroses, Tony decides to bring in an expert in business psychology. Meanwhile, Sarah's personal life may be settling down when she and her boyfriend step up their relationship.
Sarah finds herself at odds with both Mason and the director of the team's Dove commercial when she and the director disagree and Mason fails to back her up. Meanwhile, Tony recruits Conner to help him steal a forgotten account from another group, which drives an even larger wedge between Conner and Mason.
Mason finally gets the recognition he so desperately craves when Denise gives him the credit, and another promotion, for winning a massive account for the team. While Conner gets an update about his short-lived relationship with Diane, Sarah is questioning whether to continue her current relationship or the best way to end it.