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.

This week, Jen and Paul dissect a "Safety Specialist" job ad that’s equal parts essential and exploitative. Tasked with handling everything from suicides to human trafficking, this role is adjacent to the dark underbelly of the gig economy—yet the ad offers zero clarity on training, team structure, or mental health support. With a lowball salary and a call centre vibe masquerading as a "specialist" role, is this a necessary function or a systemic failure with potentially real harms for real people?

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/ep-015-behind-the-lockbox

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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 are joined by Dr. Sam Illingworth to roast a "Lecturer in Law" job ad from a prestigious UK university. The ad demands "excellence" in teaching and scholarship, but what’s missing? Career support, clear metrics for success, and any real acknowledgment of the emotional labours required. Sam, an insider with two decades in academia, reveals why this role is both coveted and flawed, from the unpaid "service" work to the systemic undervaluing of teaching. Is this the future of higher education, or just another example of institutional gaslighting? Tune in to find out.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/ep-014-last-lap-for-tenure-track

You can find Sam's excellent Substack, The Slow AI, here: https://theslowai.substack.com/

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

Special Bonus Episode:

Jen and Paul circle back on Episode 010, where they co-designed a job ad for a role that Jen was hiring for at her firm. Update: she sent out an offer letter this week. In this short bonus episode, they reflect on the human-centric hiring process used and how it connected to the job ad design.

Catch the original episode here:

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

You can find the show notes and goodies from this bonus episode here:

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

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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 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.