Struggling advertising executive Roger Newhouse wants to quit the business and become a musician; no-nonsense Maggie tries to convince cocky boyfriend Sanjay to attend couples therapy; alpha-boss Bob arrives from New York for a showdown with Roger.

Roger finally reveals that he has landed a coveted pitch with Pear Computer; Maggie discovers just how badly Roger has managed the agency in her absence; Bob hatches a plan to get Maggie and Roger back together to ensure he wins the Pear pitch.

Maggie makes a decision about working with Roger; the agency is visited by an oddball creative team (Hamilton's Lin-Manuel Miranda and Irene Lucio) who offer their prodigious talents for the Pear pitch; over-worked account executive Caitlin (Eirinie Carson) begins to question her loyalty to Roger.

Roger shares a cathartic experience with the guy who used to water his plants; Maggie reads the riot act to Sanjay and avoids repeating history; Bob and Caitlin begin to bond over coffee and racial injustice.

In a last-ditch attempt to finish the pitch on time, Roger bares his soul; Maggie comes to terms with her past relationships; with Roger AWOL, Bob and Caitlin decide to present the pitch themselves.

Roger has a rude awakening and scrambles to get his plan to fix everything back on track; Maggie, Bob and Caitlin crack open a bottle of champagne; we finally discover who Enoch Bartlett is.