Eighteen new candidates meet up with Donald Trump in a New York City airport to be divided into teams and set out on their first mission. After preliminary details, the task, to market Sam's Club using massive blimps, is revealed. Allie leads her team, Synergy, to a close victory against Tarek's team, Gold Rush, which loses mostly because of his lack of a creative theme and Summer's ineptitude in marketing. Synergy is treated to a glimpse of life as a billionaire. Gold Rush, meanwhile, is sent to the boardroom. Tarek is nearly fired for his poor leadership, but for stupidly interrupting Trump when he is about to fire Tarek, simply to say something incredibly irrelevant, Summer is fired instead.
The Donald presents the next task to the candidates: promote a new razor by getting New Yorkers to send text messages to a phone number. Under the supervision of Bill Rancic and newcomer Ivanka Trump, Trump's daughter, Synergy Corporation fumbles with any sense of advertising scheme, and when it comes to location, they pick an unpopulated area that not many people go to. Gold Rush, however, does quite well despite struggling with leader Lee, who is whipped into shape by Lenny. In the end, Gold Rush trumps Sunergy, and in the boardroom, Project Manager Pepi, as well as the rest of the team, blames the loss on the obnoxiously different Brent. Pepi brings Brent, Stacy, and Michael back into the boardroom, but ultimately, the boss decides to keep Brent around for another week and fires both Stacy and Pepi.
The candidates must throw a corporate retreat for car-dealership owners.
The contestants design billboards to launch a new product for a cereal company.
The remaining candidates must create a new commercial for Norwegian Cruise Lines. Project Manager Roxanne, faced with initial resistance from her team, manages to lead Synergy to a decisive victory by creating a great, original commercial. Project Manager Dan, on the other hand, makes so many mistakes, including failing to utilize all of his teammates and going with a bad concept from Lenny, and leads Gold Rush to defeat. Synergy gets rewarded with a trip to the Brinks Diamond Vault to take home ,000 worth of diamonds. Gold Rush goes to the boardroom, where, despite Tarek's many boardroom appearances, Trump fires Dan for his bad leadership and bringing Lee into the boardroom instead of Lenny.
The twelve remaining candidates are challenged to write an advertising jingle for Arby's. Synergy immediately gets off to a good start when Project Manager Sean has them meet with their client right off the bat. Thanks to the input they are able to obtain, they manage to put together a very catchy jingle hitting on every aspect of Arby's. Gold Rush, already a man down because of Lee's absence, gets off on the wrong foot when Charmaine schedules a meeting with the client that Project Manager Bryce gets them to 25 minutes late. With less time to get any decent input, the team puts together a decent jingle that lacks a crucial bit of info, giving the win to Synergy. For their reward, they dine at the luxurious Alain Ducasse restaurant. Gold Rush goes to boardroom, where Bryce refuses to hold Tarek and Charmaine accountable for the loss, instead trying to hold Lenny and Lee responsible. Trump sees this as a stupid mistake and fires Bryce for it.
The eleven remaining candidates are assigned to create activity areas to benefit a children's charity in a renovation-themed task.
The remaining candidates launch a new pizza sandwich for 7-Eleven.
Trump's children, Ivanka and Donald Jr. fill in for Carolyn and George for this task, which requires the remaining candidates to promote one of New York City's biggest tourist attractions. The winning team is treated to a round of golf while the losers are sent to the boardroom, where another candidate is fired.
And then there were eight. The candidates dive into a hair-raising challenge in which they must oversee the grand openings of two hair salons. Along the way, a potential love match comes to light. The winners then work with songwriter Burt Bacharach.
The remaining candidates tackle a challenge to throw a tailgate party at a college football game, with one team cooking up plans for an eating contest. The winners then head out to the country, where they're wined and dined.
The remaining five candidates must create a store display for the new Xbox 360 at Wal-Mart. Real life meets reel life for the winners when they jet off to the West Coast to meet film executive Jeffrey Katzenberg, who gives them an opportunity to participate in a voiceover session for the animated movie Over the Hedge.
The remaining four candidates are tasked with creating a new line of uniforms for an upscale hotel chain. The winners then enjoy some time out on the town.
The final two candidates are challenged to coordinate two high-profile charity events. Lee works with the returning Lenny, Pepi, and Roxanne to organize a celebrity hockey event. Sean works with the returning Tammy, Andrea, and Tarek as he tries to hit all the right notes while staging an Atlantic City rock concert featuring Barenaked Ladies.
The finalists scramble to complete their most difficult tasks to date, then go head to head in the final boardroom. The winner is announced live from Los Angeles.