Roast the Post
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Most job postings are treated like boring admin documents. They’re not.
Job ads are compressed expressions of how an organization thinks about work, power, risk, and people. What gets listed, omitted, what’s vague, what’s conflated, and what’s really being offloaded onto “other duties as assigned.”
Roast the Post is a weekly show that takes real job postings and breaks them down, line by line, to uncover what they actually signal about the role and the organization behind it.
We don’t name-and-shame companies, and we don’t pretend that the labour market is broken because people are “doing it wrong.” Instead, we analyze job ads and treat them as the hidden decoder ring that they are.
What happens in an episode
Each episode centres on a single, real job posting. One host brings it to the table; the other sees it cold for the first time while sitting in the hotseat.
We read it aloud, section by section, and pause to discuss :
What the role is really asking one person to do
Where responsibilities, authority, and accountability don’t line up
What the posting reveals about structure, culture, and decision-making
Which signals are helpful, and which are red flags
We close each episode by scoring the post and explaining why. Agreement is optional. Perspective is not.
If you’re a job seeker
This show helps you read postings more critically so you can :
Avoid roles that are mis-scoped, under-supported, or, frankly, unworkable
Prepare better questions for interviews
Make informed tradeoffs instead of hopeful guesses
The goal isn’t to talk you out of work, but to help you make informed decisions. You won’t always be in a position to be selective about your offers, but you can at least walk in with your eyes wide open.
If you’re hiring (or designing roles)
This show will challenge how you think about job postings as a tool for building a better organization and more resilient teams.
You’ll see how small wording choices signal big structural issues, and how unclear roles create downstream problems like burnout, churn, and missed expectations. Not because people are bad at hiring, but because role design is rarely treated as a discipline.
If you care about attracting better candidates and setting them up to succeed, this will be uncomfortable in the most useful way possible.
About the Hosts
Jennifer Houle
Jennifer Houle has spent nearly two decades inside organizations, building, advising, fixing, and pulling apart the systems that shape how people work.
She’s currently VP, People Operations at Raven Capital, where she supports multiple companies and advises venture-backed founders on values-aligned, legally sound, and actually built-to-handle real-world complexity people systems. Her work lives at the intersection of HR, leadership, power, and trust.
Jennifer also writes Uncompliant, a space for people who sense that something about work isn’t actually working… and want to understand why. Her writing focuses on organizational design, entrenched practices, and the gap between what companies say they value and what their systems actually reward.
On Roast the Post, she brings a people and culture lens that cuts past surface-level advice. She’s interested in how job postings encode expectations, where responsibility gets offloaded, and how “standard practice” often becomes a problem when no one stops to question it.
Jennifer is deeply skeptical of lazy role design, performative hiring, and systems that expect humans to absorb structural failures beyond their control.
That’s why she’s here.
Paul Austin-Menear
Paul Austin-Menear’s spent his career inside growing companies—building teams, scaling operations, and dealing with what happens after the org chart looks good on paper.
He’s an operator by trade, with deep experience in organizational design, operational leadership, and entrepreneurship across technology, manufacturing, and consumer businesses. He’s worked inside startups and scale-ups, led cross-functional teams, and held roles where vague mandates and poorly designed jobs turn into very real delivery problems.
Paul is the founder of Six Catalysts, where he works with founders and leadership teams on operational clarity, role design, and systems that actually scale. His focus isn’t theory—it’s how decisions show up in workflows, incentives, accountability, and day-to-day execution.
On Roast the Post, Paul approaches job postings as early warning systems. He looks for where expectations outpace authority, where scope balloons, and where “this seemed reasonable at the time” turns into burnout six months later. If a role is structurally set up to fail, he’s usually the one pointing to how and why.
Paul isn’t anti-ambition or anti-growth.
He is allergic to hand-wavy roles, overloaded individual contributors, and organizations that confuse optimism (or lack of thought) with purposeful design.
Together with Jen, he brings the operator’s counterweight to the people lens because good intentions don’t survive bad structure on hopes and prayers alone.
Studio Audiences
New episodes are recorded in front of a live audience in the virtual studio every Friday afternoon. You can join any recording for free—subscribe for an invite!
