Doug pops the question to his girlfriend, Sarah (JENNY SLATE), who plans a shotgun wedding in Las Vegas on the eve of the Pod closing a major business deal. Marty's backhanded dealings lead to increased tension and unintended consequences for everyone.

Marty is pushed to the brink when trying to finalize a business deal with erratic and temperamental Las Vegas casino magnate, Michael Carlson. Clyde sees his star meter rising when his club owner pals, the Dushkin twins, turn to him to extend their brand beyond Las Vegas. Marty learns privileged information about Tamara.

Marty covertly makes strides with his future in mind and Jeannie questions her own future when presented with a great career opportunity. Doug must overcome his fear of navigating social settings when a chance to "rain make" some of his own business falls into his lap. Meanwhile, at home, tensions come to a head with Marty and his brother, Malcolm.

Doug and Clyde are summoned to testify in a legal deposition for their role in a wrongful death suit filed against a big telecommunications company. Casino king Michael Carlson slows Marty's attempts to close a deal. Monica begins to unravel after Roscoe moves out.

Jeannie meets an unlikely suitor, Nate (ADAM BRODY), when consulting with an adult toy company. While on the engagement, Doug is struck with inspiration for a wild gift idea for his new girlfriend. Meanwhile, Marty's brother Malcolm (LARENZ TATE) begins to drive a wedge between Marty and their father.

Marty faces a moral dilemma when he discovers evidence of a banking client's role in a cover-up scheme. Jeannie attempts damage control with the Pod when an ex-boyfriend posts something shocking on the web.

Marty questions his commitment to Galweather Stearn when events at an executive retreat conflict with his plans to do something important for Roscoe. Doug gains a new perspective on his fellow Pod members after introducing them to his girlfriend Sarah (JENNY SLATE). Marty is tempted to explore things with Tamara (NIA LONG) after she makes a startling admission about her personal life.

Marty gets a surprise visit from his militant younger brother, Malcolm (LARENZ TATE), whose reasons for resurfacing after three years seem dubious. Elsewhere, Doug and Jeannie go on assignment with an online dating company while Marty finds a kindred spirit in political consultant Brynn (LISA EDELSTEIN) while on an engagement with a banking CEO.

When superstar Matt Damon (HIMSELF) calls on Galweather Stearn to find him a charity to enhance his image, Marty discovers he may have to go further than he's willing to keep Damon's business. Elsewhere, Jeannie spends time with Roscoe whileTessa presses Monica about their status.

Marty and Clyde attempt to woo the business of new Las Vegas casino king, Michael Carlson, a maverick self-made millionaire who notoriously hates consultants. Meanwhile, Jeannie tries to assess how big a threat Tamara (guest star Nia Long) is by suggesting the two of them enjoy a spa day together. Monica makes an unlikely connection with her personal vegan chef.

Marty and the Pod head to Las Vegas to help an aging casino regain its luster. They're joined by Tamara (guest star Nia Long), Galweather Stearn's newest consultant and Marty's business school rival. Clyde is seduced by the VIP bottle-service Las Vegas nightlife. Jeannie finds a passive-aggressive foe in Galweather Stearn's interim CEO, Julianne.

Marty and the Pod adjust to the "new" Galweather Stearn in the aftermath of the sexual harassment scandal. Interim CEO, Julianne Hofschrager, needs Marty to live up to his reputation of being a fearless closer but that expectation poses a challenge when Marty consults with Mr. Pincus, a valued client no one in the company knows. Meanwhile, Jeannie relives haunting memories from a drunken night out and Marty struggles to patch things up with his son Roscoe.