Struggling advertising executive Roger Newhouse (Anthony Veneziale) wants to quit the business and become a musician; no-nonsense Maggie (Chrissy Mazzeo) tries to convince cocky boyfriend Sanjay (Pitch Perfect's Utkarsh Ambudkar) to attend couples therapy; alpha-boss Bob (Don Reed) 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.
