When Mason wins a promotion within the advertising agency, he must leave behind his best friend Connor. This forces them to reexamine their relationship as both brotherly friends and colleagues in the fiercely competitive ad agency world.
Connor must save the day when a client rejects a pitch, which puts Mason's job on the line. Meanwhile, Sarah adds Mason's anxiety.
Mason risks it all by promising the company CEO that Sarah will lead the team to complete success. However, this proves to be easier said than done as Sarah begins to consider other job offers.
Mason gets into an ad campaign problem after reneging on a promise he made to a client. Mason's latest pitch falls short after basing his abnormal teenage daughter's habits which don't exactly translate to all teens her age. Meanwhile, Hector and Tom have a battle over who will escort Sarah to a party.
Connor makes a bold move by continuing to produce an ad after the client pulls the plug to rethink the entire campaign. Meanwhile, Sarah tries to get back together with her ex-husband and Tony receives devastating news.
In hopes of latching onto a coveted account for Chicago's Olympic bid, an ad group decides to network. Mason grudgingly hands over the Conner managerial control for the group so he and Erin can have a long-weekend at a Ritzy Chicago hotel. Meanwhile, Sarah ads a new partner who left the ad business earlier to raise her children.
Mason and Conner both seek employment when hit by financial difficulties. But they find a lack of trust between each other as they discover their secrets. Elsewhere, a shampoo account has Sarah up to her neck with problems. And, Tom finds himself involved in an interoffice romance.
The Mink Group's chances of landing a new energy drink may be jeopardized by a concealed relationship of a team member. Elsewhere, Sarah uses a dating service to find a love match. And Mason's wife believes he may have a roving eye, so she shows up to his office unexpectedly.
Conner's ex-creative partner is offered freelance work by him, only to discover he doesn't posses the skills needed for the job. Meanwhile, Sarah looks into a high profile beer account, which causes Mink nemesis Simon Cochran to be drawn aware. Back at the McGuire home, Mason attempts to help daughter Haley with her romantic growing pains, which backfires.
The agency taps into an imported beer account, but find that all is not bubbly as Tony spirals into an uncontrollable rage after learning that adversarial Cochran Group is allowed to join in the pitch. Meanwhile, Conner unearths office secrets while shooting a tribute to Tony for his birthday.
Mason receives an unfavorable evaluation at work, causing an angry outburst and Tony to hire a corporate therapist to help the group through a number of issues. Meanwhile, Sarah finds her new relationship blossoming and seeks the blessing of her ex-husband, only to discover the brutal truth of why he divorced her.
A soap product's commercial shoot becomes chaotic when Sarah tangles with the director, which causes friction between herself and Mason. Then Tony gets his hands on a rival group's account and delegates Conner as his partner in the act, making a further rift between Conner and Mason.
Season one closes as the Mink group wins a crucial account, inspiring Denise to offer Mason a huge promotion. Elsewhere, Conner receives important news concerning his affair with a marketer from a energy drink client; and Sarah thinks over which way would be best to break up with her boyfriend.