Season 5

Now that Pied Piper has ample funding and new offices, the pressure to get things right stymies Richard and forces him to grow the company in a way he hadn't planned. A picky Dinesh and Gilfoyle question their ability to make good decisions. After returning to Hooli, Gavin worries about becoming antiquated.

Panicked by suddenly leading a much larger team, Richard finds himself managing a number of small conflicts in his efforts to unite his new employees. Dinesh celebrates a new purchase that Gilfoyle looks to spoil. Jian-Yang goes to court. Gavin meets pushback over his signature and what it says about him.

Encouraged by Jared to strike up a friendship with Dana, a like-minded CEO, Richard instead finds himself charmed by Dana's COO, who challenges his loyalty to Gilfoyle. Facing limited housing options thanks to his impulse purchase, Dinesh searches for a new roommate.

Attempting to woo a gaming company to PiperNet, Richard inadvertently angers a prized ally. Dinesh deals with a betrayal. In preparation for a big launch, Gavin leaves his underlings with a cryptic message. Jared gets inside information from Big Head.

Overshadowed by Jared in an on-camera interview, Richard’s confidence wavers further when Laurie and Monica force him to work with Eklow, a new artificial-intelligence company. Gilfoyle worries about the prospect of introducing AI into Pied Piper. Dinesh makes Jared self-conscious ahead of a second interview. Gavin questions his future beyond Hooli.

Richard decides to help when Laurie gets in a jam, but his lack of emotional discipline threatens to backfire on Pied Piper. Gavin tries to make a deal with a stubborn partner while abroad. Dinesh relishes a rare win. Jared bonds with a surprising figure.

As the Pied Piper guys prepare to close on their Series B funding, Richard receives some unsettling news. Gilfoyle suggests a risky proposition and Monica gets blunt with Richard. Dinesh goes to great lengths to compete with a coworker, while Jared keeps close watch on Richard's new assistant. In search of a better deal, Gavin tries to charm small-town America.

PiperNet launches, but an early success makes Monica suspicious; Richard makes a surprising move; the team races against the clock as its future is threatened.