Roast the Post Podcast

Golf Companion: Singapore Sling, Toronto Swing.

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 [https://roastthepost.substack.com/p/golf-companion-singapore-sling-toronto-swing] -- Jen and Paul roast weekly at https://roastthepost.show [https://roastthepost.show]. Subscribe to catch new roasts as they drop. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.substack.com [https://roastthepost.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Product Designer: Worshipping at the Altar of Figma

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 [https://roastthepost.substack.com/p/product-designer-worshipping-figma-altar] — Jen and Paul roast weekly at https://roastthepost.show [https://roastthepost.show]. Subscribe to catch new roasts as they drop. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.substack.com [https://roastthepost.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Director of Pedagogy: Peda... goo-goo? With Chief Absurdist Officer

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 [https://roastthepost.substack.com/p/director-pedagogy-pedagoogoo-chief-absurdist-officer] — Jen and Paul roast weekly at https://roastthepost.show [https://roastthepost.show]. Subscribe to catch new roasts as they drop. — You can check out Kathi's work Hello, Human and NOT RISING here: https://chiefabsurdistofficer.substack.com/ [https://chiefabsurdistofficer.substack.com/] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.substack.com [https://roastthepost.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Roast the Post LIVE: Happy Hour

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. -- Jen and Paul roast weekly at https://roastthepost.show [https://roastthepost.show]. Subscribe to catch new roasts as they drop. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.substack.com [https://roastthepost.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

VP, Enterprise Sales: The Scorpion and the Frog at the River

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 [https://roastthepost.substack.com/p/vp-enterprise-sales-the-scorpion-frog-river] -- Jen and Paul roast weekly at https://roastthepost.substack.com [https://roastthepost.substack.com]. Subscribe to catch new roasts as they drop. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.substack.com [https://roastthepost.substack.com?utm_medium=podcast&utm_campaign=CTA_1]