Executive Assistant & Office Manager: Two Jobs in a Trench Coat

Roast the Post Podcast · Jan 23, 2026 · 58m · transcript

This week Jen drops a deceptively “cool mission” job post: executive assistant and office manager at a polar expedition travel company… and the bullets just keep coming. Calendar wrangling for the president plus five other execs, expenses, decks, events, vendors, fridge clean-outs, building access, and even health & safety committee work—paired with “flexible hybrid,” 10 vacation days, and no salary range. Jen and Paul dig into what this posting signals about org design, hidden workload, gender-coded expectations, and why “discretion” shows up like a warning label.

If you’ve ever wondered how…