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

--

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

--

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

--

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

This week, Jen and Paul head to Victoria, BC to “roast” a barista posting from a mega-brand that actually knows how to write: clear role fit, community vibe, and benefits that are almost suspiciously strong (yes, even for part-time). But then the real questions hit: what does “reasonable accommodation” mean in a physically demanding, high-chaos service job? Why don’t they spell out lifting/standing realities? And what happens when “no experience required” meets a menu built for maximum customization... and customers having a bad day? If you’re applying, you’ll learn what to look for between the lines. If you’re hiring, you’ll learn how to communicate values by showing your policies, not just reciting slogans.

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

https://roastthepost.substack.com/p/ep-009-steam-that-sandwich

--

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

This week on Roast the Post, Jen and Paul head to St. John’s, Newfoundland to dissect a Loan Consultant role at a national alternative lending organization. Is it a friendly “consultant” position, or a retail banking sales job in disguise? From uncapped bonuses and 7% RRSP matching to AI disclosures and background checks, they unpack what the posting reveals about structure, transparency, and whether you can realistically build a career at $17.52–$22.50 an hour. Surprisingly, this one doesn’t burn. Instead, it raises a bigger question about respect, clarity, and what “entry-level” roles should look like in 2026.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-008-the-consultant-who-wasnt

--

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

“Culture Coach” sounds like a dream job, until the posting starts reading like an organizational Rorschach test. Jen brings a rare one: a remote Canada role at a New York–based IT consultancy that’s trying to reinvent people ops… and accidentally tells on itself in the process. We dig into what a “culture coach” really is, why the responsibilities feel half-baked, what it signals when the first interview is a one-way video into the void, and how “benefits” magically appear twice, contradicting themselves along the way. If you’re a job seeker, this episode will help you separate innovative from incoherent. If you’re a job-seeker seeker, it’s a masterclass in how vague postings create bad applicant pools, compliance risk, and trust issues before Day 1.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-007-culture-coach-or-chaos-couch

--

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

This week, Jen and Paul test a new episode format—and immediately hit the same brick wall every job seeker hits: a job posting so long and scope-heavy it gives your tongue a cramp. They dig into a “Chief of Staff (Client Operations)” role that’s also “Client Ops Manager,” also “fractional COO,” also… whatever needs doing. Along the way, they unpack what job posts accidentally reveal about a company’s operational maturity, how “context switching” becomes a euphemism for chaos, and why “we live in the unsexy” can be either refreshing honesty or a warning label. Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-006-context-switching-as-a-love

--

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

This week on Roast the Post, Jen and Paul stumble into a job ad that feels like it was assembled after midnight with one eye open and Ctrl+C permanently stuck. It’s supposed to be a part-time woodwind instructor role—except it keeps drifting into drums, then casually tosses in piano like it’s garnish. Along the way, we get into what “seasoned” really implies about pay, why “benefits” like casual dress are… not benefits, and the awkward reality of contractor gigs where the school may be one middle-person too many. If you’re hiring, this episode is a reminder that sloppiness signals culture... and if you’re job hunting, it’s a masterclass in reading between the (very messy) lines.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-005-the-copy-paste-conservatory

--

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