Roast the Post Podcast

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

44 min · 1 de may de 2026
Portada del episodio VP, Enterprise Sales: The Scorpion and the Frog at the River

Descripción

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.show [https://roastthepost.show?utm_medium=podcast&utm_campaign=CTA_1]

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