Simon, Zach, and Andrew pitch ideas for Australia tourism, but Simon has a difficult time coming up with ideas. Sydney's former co-worker writes a song about her that she does not like. Simon uses the song for the Australia ad.
The agency hires a data analyst against Simon's wishes. They have a new client who sells cat food, and the data analyst has a better marketing idea than Simon. Sydney bonds with the cat, while Zach and Andrew try to cheer up Simon.
Someone's job is on the line at the annual Accounts vs. Creatives 16-inch softball game, and the truth about Simon's last epic win threatens to surface.
The agency promotes an advertisement for men with functioning problems. So when Simon is nominated for an advertising award next to a younger man from another agency, Simon starts to feel his age.
Simon and the team decide to use a new idea to save a library from being shut down while Gordon finds himself becoming the poster boy for the campaign.
A new client, sophisticated and classy, has Simon, Zach, and Sydney falling all over themselves to be liked the best. Helena likes them all and it causes jealousy with the three.