Marty and The Pod travel to New York to consult for MetroCapital, a bank looking for a plan to unscrupulously justify their year-end bonuses as the financial world around them burns, but Marty makes an enemy of Greg Norbert, MetroCapital's number two executive. Back at home, Marty receives unwanted parenting advice from his live-in father Jeremiah when his son Roscoe decides to audition for the female lead in a school play.
Marty and The Pod are sent to Phoenix to clean up a mess at a very powerful sports franchise caused by the impending divorce of its high-powered owners. Jeannie takes a dinner meeting with Derek, an old flame, but is deflated when she finds out his real intentions toward her. On the home front, Marty continues his personal war with Principal Gita over Roscoe's cross-dressing.
Marty arrives at the offices to find Greg Norbert there to announce the possible acquisition of Galweather by MetroCapital; the Pod flies to Indiana to consult for a beverage company, where Marty applies his management skills to turn a loss into a win; Clyde questions whether Doug really hooked up with a transvestite; Roscoe struggles with the confusing feelings of liking both a boy and a girl.
With Jeremiah out of town, Marty is forced to bring his son Roscoe to his next job in San Francisco; hoping for some quality time with his dad, Roscoe ends up spending it all with the Pod when Marty is forced to babysit Alex Katsnelson, the teenage CEO of a security software company. Meanwhile, Jeannie reacts to her recent engagement by having a tryst with Kurt, a tortured musician she randomly meets in a coffee house.
On a consulting gig in Utah, Jeannie is put in charge when it becomes clear that the racist CEO of a no-frills motel chain won't take Marty seriously; Clyde tries to make inroads with a virginal Mormon woman; Monica decides to spend some quality time with Roscoe after her married boyfriend rejects her, but their parent-son bonding takes a dark turn, leading Roscoe to better understand his mother ... and better appreciate his father.
Marty goes to war with his son's school when Roscoe is accused of sexual harassment for trying to kiss a boy. On the home front, Marty's personal life is further complicated when April, a stripper he met in New York, suddenly reappears. Meanwhile, Jeannie starts to get cold feet at the prospect of her upcoming wedding.
When the Pod goes to Washington D.C. to consult for a pharmaceutical company, Marty faces a challenge from April to stay monogamous on the road, which puts Jeannie in the position of having to "take one for the team" and fully satisfy a female client; Jeremiah reveals something serious to April, asking for her discretion until he can tell Marty himself; a jealous Monica drops a huge bombshell on Marty.
Marty and the Pod participate in Galweather-Stearn's annual recruiting event, where the best and brightest from Harvard Business School are wined and dined. Marty takes the sole black recruit in the predominantly white affair under his wing; Doug tries to prove to Clyde that he can coach any of the potential candidates onto "the list;" Jeannie grills a sexy, flirtatious recruit to see if she's all style and no substance, but a secret of Jeannie's is revealed that makes her stance somewhat hypocritical.
Marty and the Pod are put through the ringer by their arch-rival firm Kinsley-Johnson as part of the due diligence performed by MetroCapital for the pending merger; Jeannie does her best to keep Wes and the marriage at bay but fails to keep it a secret from Marty; Monica and Roscoe bond but Marty learns about Jeremiah's secret and receives shocking news from Monica.
Jeannie embarks on a gig to establish her own legend in the consulting world when she leads the Pod to her hometown on a mission to resurrect an ailing church; Marty enters into custody mediation with Monica but her powers of manipulation are in full force, threatening Marty's relationship with April.
Marty and "The Rainmaker" work together to put the kibosh on their firm's acquisition by MetroCapital but a back-stabbing turn of events leaves Marty and "The Rainmaker" mortal enemies instead of valued allies; in the aftermath of the news about April, Marty must deal with attitude from Roscoe.
With the help of Greg Norbert, Marty and the Pod fight to pull off an eleventh-hour reprieve and stop the MetroCapital acquisition from happening; Jeannie makes a decision about marrying Wes; Marty's son Roscoe makes a life-altering choice of his own.
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.
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 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 is by suggesting the two of them enjoy a spa day together. Monica makes an unlikely connection with her personal vegan chef.
Matt Damon calls on Marty to help him enhance his image.
Marty gets a surprise visit from his militant younger brother, Malcolm, 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 while on an engagement with a banking CEO.
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. Marty is tempted to explore things with Tamara after she makes a startling admission about her personal life.
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.
Jeannie meets an unlikely suitor, Nate, 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 begins to drive a wedge between Marty and their father.
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.
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
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
Season 2 finale. 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.