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.

This week on Roast the Post, Paul and Jen flip the script. Instead of tearing down a job ad, they build one on the spot. What starts as an “Executive Assistant” role quickly morphs into something closer to an operations architect inside a small, impact-focused venture capital firm. They debate title coding, gender bias, Indigenous representation, autonomy vs. micromanagement, AI disclosures, PII ethics, compensation bands, rollover policies, and whether four pages is clarity… or chaos. If you hire, manage, or apply for jobs, this episode pulls back the curtain on how thoughtful design (or lack of it) shapes candidate pools, culture, and long-term success.

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

https://roastthepost.substack.com/p/ep-010-jen-and-paul-write-a-job-ad

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