This week, Paul and Jen dissect a Director of Compliance Operations job ad that’s equal parts fascinating and terrifying. With a dual reporting structure pitting the Chief Commercial Officer against the Chief Anti-Money Laundering Officer, this role is a pressure cooker of conflicting priorities, ambiguous authority, and a salary that doesn’t match the stakes. Is this a career opportunity or a career-ending trap? Tune in to find out.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/ep-013-between-a-rock-and-a-regulator

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Jen and Paul roast weekly at roastthepost.substack.com. Subscribe to catch new roasts as they drop.

This week, Jen and Paul sink their teeth into a job ad so specific, it’s almost surreal: Dog Nanny & Household Coordinator for a private family office. The role promises “trust-based scheduling,” overnight stays, and a “competitive monthly salary” (unh-hunh), but delivers zero clarity on pay, hours, or how to balance this gig with, you know, having a life.

Is this the ultimate flex for dog lovers, or a masterclass in how not to design a job? Watch or listen to find out.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/ep-012-trust-falls-dog-balls

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Jen and Paul roast weekly at roastthepost.substack.com. Subscribe to catch new roasts as they drop.

Roast the Post gets its first listener-submitted job ad—and it’s a doozy. Ryan from Peterborough, Canada sends in a “Chief of Staff” role that reads less like a right-hand partner and more like a one-person corporate Swiss Army knife: recruiting, sales uplift, AI deployment, product launch, investor intelligence, and “unblocking the business” without permission. Jen calls it a crime against humanity (0/10). Paul splits the difference: the job sounds brutal, but the ad is unusually honest about the intensity (6/10). If you’ve ever wondered what a posting reveals about culture, power, and how much your life they’re expecting you to donate… this one’s a masterclass.

Full job ad and notes for job-seekers and hiring managers here :

https://roastthepost.substack.com/p/ep-011-the-junk-drawer-executive

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Jen and Paul roast weekly at https://roastthepost.substack.com. Subscribe to catch new roasts as they drop.