Ever seen a job ad that feels like it was written by a time traveler? This week on Roast the Post, we dissect a Communications Associate role for a nonprofit preserving Revolutionary War battlefields in the United States... where the biggest twist isn’t the history, but the ban on social media.

That’s right: no tweets, no posts, just… print ads and event logistics? Jen, Paul, and guest roaster Katelyn McArdle from Functional Authority unpack the bizarre contradictions, from the "entrepreneurial" spirit clashing with the "follow-the-rules" vibe to the salary range that’s almost fair (if the role weren’t so confusingly scoped). Is this a hidden gem for history buffs, or a dumpster fire waiting for an unsuspecting comms pro? Tune in to find out.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.show/p/communications-associate-musket-smoke-on-water

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

Ever wondered what it’s like to be the person keeping high rollers happy in the world of monetized gaming? This week, Jen and Paul dive into a Lead VIP Host job ad that’s as bold as it is vague. From the allure of autonomy to the fine print of “unlimited vacation,” they roast the post and ask: Is this the dream gig for a charismatic hustler, or a recipe for burnout? Tune in to find out if this job ad hits the jackpot or folds under pressure.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/lead-vip-host-the-whale-who-loved-me

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

What does it take to be a full-time golf companion for a jet-setting family? This week, Jen and Paul tee off on a job ad so niche, it makes their previous roasts look like entry-level gigs. Between the 75% travel, the cultural tutoring, and the mystery of who’s footing the bill for rent in Singapore, this role is equal parts dream job and logistical nightmare. Is it a legitimate opportunity or a scam wrapped in a country club membership?

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/golf-companion-singapore-sling-toronto-swing

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

Mission-driven or mission impossible? Jen and Paul dissect a product designer job posting that promises to ‘redefine healthcare’... but leaves out critical details like benefits, reporting structure, and actual responsibilities. The ad hooks you with bold language and a compelling mission, but the fine print reveals a chaotic, high-pressure role with a tiny salary range and a bizarre application process (including a mandatory video pitch).

Is this a dream job for a passionate designer, or a hustle culture trap? Listen as we roast the red flags, question the company’s priorities, and ask: If healthcare is so broken, why isn’t this company fixing its own job ads?

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/product-designer-worshipping-figma-altar

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

This week, Jen and Paul are joined by Chief Absurdist Officer (Kathi Eric Dalguntas) to roast a "Director of Pedagogy, Learning & Instructional Design" job ad that’s equal parts baffling and infuriating. The role demands a unicorn: someone who can develop curriculum, manage projects, support sales, and navigate international cultural sensitivities... all while being paid a salary that’s more laughable than livable. The ad is a Frankenstein of responsibilities, with no clarity on reporting structure, no cultural hooks, and a salary range that’s a slap in the face. Kathi, Jen, and Paul dissect why this role is doomed to fail, why the company’s mission is buried under a mountain of red flags, and what job seekers should really ask if they dare apply.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/director-pedagogy-pedagoogoo-chief-absurdist-officer

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

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You can check out Kathi's work Hello, Human and NOT RISING here: https://chiefabsurdistofficer.substack.com/

Jen and Paul are live from a Toronto pub, ripping into the worst of hiring: the radio silence after applying, the salary question trap, and the myth of "cultural fit." They spill the tea on how to handle lowball offers, when to walk away from a toxic workplace, and why your next job’s hiring process might be a red flag in disguise. Plus, hot takes on digital nomad life, the absurdity of unpaid "trial workdays," and why every new hire deserves a paid first week off. This isn’t just a roast, it’s a survival guide for job seekers and a wake-up call for hiring managers.

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

This week, Jen and Paul tackle a Vice President of Enterprise Sales job ad from a nonprofit tech platform, and it’s a doozy. With a $25M revenue target, a team of 40+ direct reports, and a compensation structure that’s more mystery than transparency, this role is a masterclass in how not to design a job. The ad screams capitalism but serves charities, raising serious questions: Who’s really benefiting here? And why is a role this demanding so light on details about authority, reporting structure, and even base salary?

From the ethical tightrope of incentivizing sales in the nonprofit sector to the logistical nightmare of managing a team this size, this episode dives deep into the systemic flaws hiding in plain sight. Plus, Jen and Paul debate whether “executive presence” is just code for old-school bias, and why this job ad might be setting up its hires for failure.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/vp-enterprise-sales-the-scorpion-frog-river

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

This week, Paul and Jen roast a Senior Manager, Partner Success job ad for a tiny CPG startup network... and uncover a classic scaling mistake: hiring a clone of yourself. The role? A chaotic mix of sales, operations, event planning, and team leadership, all wrapped up in a “player-coach” philosophical bend. But with 20-30% travel, a vague team structure, and a salary that suggests high stakes, is this a bold bet on growth or a recipe for disaster?

We dig into why founders often default to replicating their own skill sets (hint: it’s not strategic), the red flags in role design, and what this ad reveals about the challenges of scaling a scrappy startup. Plus, Jen and Paul debate whether this job is even doable, or just a fantasy of what one person could do if they never slept.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/the-cpg-hunger-games

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