Marty and the Pod attempt to get a boy band to re-sign with their record label; Jeannie gets fed up being a politician's girlfriend; Doug deals with his post-Ted Talk "fame" and the repercussions it has on relationships.
Marty reluctantly reunites with a couple of his most objectionable past clients in an attempt to expand the business of a major cruise line; Clyde gets in the way of Doug fulfilling his high-seas fantasy; Jeannie gets emotional over her baby.
Marty competes with Monica for new business and learns she's been offered a lucrative deal. Meanwhile, Jeannie gets romantic with a client, despite his questionable past; Clyde is tapped to join a new venture; and Doug obsessives over the opportunity to give a Ted Talk.
With Jeannie back at K&A, Marty and the Pod consult for a new company trying an unconventional management style. Meanwhile, Doug wonders if there is a possibility of romance with K&A's newest client; and Clyde experiences an ill-timed breakup.
Season 5 begins with Marty back on top and navigating the hazards of co-parenting with Jeannie, along with each other's new relationships. Meanwhile, Doug and Clyde maneuver for position; and a familiar face from the past approaches Marty with an intriguing offer.