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.