Roast the Post Podcast

Lead VIP Host: The Whale Who Loved Me

Paul Austin-Menear and Jennifer Houle — Fri, 29 May 2026 07:21:00 GMT

Ever wondered what it’s like to be the person keeping high rollers happy in the world of monetized gaming? This week, Jen and Paul dive into a Lead VIP Host job ad that’s as bold as it is vague. From the allure of autonomy to the fine print of “unlimited vacation,” they roast the post and ask: Is this the dream gig for a charismatic hustler, or a recipe for burnout? Tune in to find out if this job ad hits the jackpot or folds under pressure.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/lead-vip-host-the-whale-who-loved-me

Jen and Paul roast weekly at 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.show

Golf Companion: Singapore Sling, Toronto Swing.

Paul Austin-Menear and Jennifer Houle — Fri, 22 May 2026 07:17:00 GMT

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

Jen and Paul roast weekly at 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.show

Product Designer: Worshipping at the Altar of Figma

Paul Austin-Menear and Jennifer Houle — Fri, 15 May 2026 07:09:00 GMT

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

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Jen and Paul roast weekly at 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.show

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

Paul Austin-Menear, Jennifer Houle, and Chief Absurdist Officer — Fri, 08 May 2026 07:05:00 GMT

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/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit roastthepost.show

Roast the Post LIVE: Happy Hour

Paul Austin-Menear and Jennifer Houle — Tue, 05 May 2026 16:06:00 GMT

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. 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

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

Paul Austin-Menear and Jennifer Houle — Fri, 01 May 2026 07:11:00 GMT

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

Jen and Paul roast weekly at 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

Senior Manager, Partner Success: The CPG Hunger Games

Paul Austin-Menear and Jennifer Houle — Fri, 24 Apr 2026 07:08:00 GMT

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

Jen and Paul roast weekly at 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

Specialist, Safety: Behind the Lockbox

Paul Austin-Menear and Jennifer Houle — Fri, 17 Apr 2026 07:11:00 GMT

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

Jen and Paul roast weekly at 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

Lecturer in Law: Last Lap for Tenure Track with Dr. Sam Illingworth

Paul Austin-Menear, Jennifer Houle, and Dr Sam Illingworth — Fri, 10 Apr 2026 07:04:00 GMT

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/

Jen and Paul roast weekly at 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

Special: Jen and Paul Write a Job Ad (Update)

Paul Austin-Menear and Jennifer Houle — Tue, 07 Apr 2026 07:04:00 GMT

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

Jen and Paul roast weekly at 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

Director, Compliance Operations: Between a Rock and a Regulator

Paul Austin-Menear and Jennifer Houle — Fri, 03 Apr 2026 07:07:00 GMT

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

Jen and Paul roast weekly at 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

Dog Nanny & Household Coordinator: Trust Falls and Dog Balls

Paul Austin-Menear and Jennifer Houle — Fri, 27 Mar 2026 07:14:00 GMT

This week, Jen and Paul sink their teeth into a job ad so specific, it’s almost surreal: Dog Nanny & Household Coordinator for a private family office. The role promises “trust-based scheduling,” overnight stays, and a “competitive monthly salary” (unh-hunh), but delivers zero clarity on pay, hours, or how to balance this gig with, you know, having a life.

Is this the ultimate flex for dog lovers, or a masterclass in how not to design a job? Watch or listen to find out.

Full job ad and notes for job-seekers and hiring managers here: https://roastthepost.substack.com/p/ep-012-trust-falls-dog-balls

Jen and Paul roast weekly at 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

Chief of Staff: The Junk Drawer Executive

Paul Austin-Menear and Jennifer Houle — Fri, 20 Mar 2026 07:07:00 GMT

Roast the Post gets its first listener-submitted job ad—and it’s a doozy. Ryan from Peterborough, Canada sends in a “Chief of Staff” role that reads less like a right-hand partner and more like a one-person corporate Swiss Army knife: recruiting, sales uplift, AI deployment, product launch, investor intelligence, and “unblocking the business” without permission. Jen calls it a crime against humanity (0/10). Paul splits the difference: the job sounds brutal, but the ad is unusually honest about the intensity (6/10). If you’ve ever wondered what a posting reveals about culture, power, and how much your life they’re expecting you to donate… this one’s a masterclass.

Full job ad and notes for job-seekers and hiring managers here :

https://roastthepost.substack.com/p/ep-011-the-junk-drawer-executive

Jen and Paul roast weekly at 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

Special: Jen and Paul Write a Job Ad

Paul Austin-Menear and Jennifer Houle — Tue, 17 Mar 2026 07:05:00 GMT

This week on Roast the Post, Paul and Jen flip the script. Instead of tearing down a job ad, they build one on the spot. What starts as an “Executive Assistant” role quickly morphs into something closer to an operations architect inside a small, impact-focused venture capital firm. They debate title coding, gender bias, Indigenous representation, autonomy vs. micromanagement, AI disclosures, PII ethics, compensation bands, rollover policies, and whether four pages is clarity… or chaos. If you hire, manage, or apply for jobs, this episode pulls back the curtain on how thoughtful design (or lack of it) shapes candidate pools, culture, and long-term success.

Full job ad and notes for job-seekers and hiring managers here :

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

Jen and Paul roast weekly at 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

Barista: Steam that Sandwich!

Paul Austin-Menear and Jennifer Houle — Fri, 13 Mar 2026 07:06:00 GMT

This week, Jen and Paul head to Victoria, BC to “roast” a barista posting from a mega-brand that actually knows how to write: clear role fit, community vibe, and benefits that are almost suspiciously strong (yes, even for part-time). But then the real questions hit: what does “reasonable accommodation” mean in a physically demanding, high-chaos service job? Why don’t they spell out lifting/standing realities? And what happens when “no experience required” meets a menu built for maximum customization... and customers having a bad day? If you’re applying, you’ll learn what to look for between the lines. If you’re hiring, you’ll learn how to communicate values by showing your policies, not just reciting slogans.

Full job ad and notes for job-seekers and hiring managers here:

https://roastthepost.substack.com/p/ep-009-steam-that-sandwich

Jen and Paul roast weekly at 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

The Loan Consultant Who Wasn’t

Paul Austin-Menear and Jennifer Houle — Fri, 06 Mar 2026 08:02:00 GMT

This week on Roast the Post, Jen and Paul head to St. John’s, Newfoundland to dissect a Loan Consultant role at a national alternative lending organization. Is it a friendly “consultant” position, or a retail banking sales job in disguise? From uncapped bonuses and 7% RRSP matching to AI disclosures and background checks, they unpack what the posting reveals about structure, transparency, and whether you can realistically build a career at $17.52–$22.50 an hour. Surprisingly, this one doesn’t burn. Instead, it raises a bigger question about respect, clarity, and what “entry-level” roles should look like in 2026.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-008-the-consultant-who-wasnt

Jen and Paul roast weekly at 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

Culture Coach or Chaos Couch?

Paul Austin-Menear and Jennifer Houle — Fri, 27 Feb 2026 08:01:00 GMT

“Culture Coach” sounds like a dream job, until the posting starts reading like an organizational Rorschach test. Jen brings a rare one: a remote Canada role at a New York–based IT consultancy that’s trying to reinvent people ops… and accidentally tells on itself in the process. We dig into what a “culture coach” really is, why the responsibilities feel half-baked, what it signals when the first interview is a one-way video into the void, and how “benefits” magically appear twice, contradicting themselves along the way. If you’re a job seeker, this episode will help you separate innovative from incoherent. If you’re a job-seeker seeker, it’s a masterclass in how vague postings create bad applicant pools, compliance risk, and trust issues before Day 1.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-007-culture-coach-or-chaos-couch

Jen and Paul roast weekly at 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

Chief of Staff: Context Switching as a Love Language

Paul Austin-Menear and Jennifer Houle — Fri, 20 Feb 2026 08:02:00 GMT

This week, Jen and Paul test a new episode format—and immediately hit the same brick wall every job seeker hits: a job posting so long and scope-heavy it gives your tongue a cramp. They dig into a “Chief of Staff (Client Operations)” role that’s also “Client Ops Manager,” also “fractional COO,” also… whatever needs doing. Along the way, they unpack what job posts accidentally reveal about a company’s operational maturity, how “context switching” becomes a euphemism for chaos, and why “we live in the unsexy” can be either refreshing honesty or a warning label. Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-006-context-switching-as-a-love

Jen and Paul roast weekly at 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

Woodwind Instructor: The Copy-Paste Conservatory

Jennifer Houle and Paul Austin-Menear — Fri, 13 Feb 2026 08:03:00 GMT

This week on Roast the Post, Jen and Paul stumble into a job ad that feels like it was assembled after midnight with one eye open and Ctrl+C permanently stuck. It’s supposed to be a part-time woodwind instructor role—except it keeps drifting into drums, then casually tosses in piano like it’s garnish. Along the way, we get into what “seasoned” really implies about pay, why “benefits” like casual dress are… not benefits, and the awkward reality of contractor gigs where the school may be one middle-person too many. If you’re hiring, this episode is a reminder that sloppiness signals culture... and if you’re job hunting, it’s a masterclass in reading between the (very messy) lines.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-005-the-copy-paste-conservatory

Jen and Paul roast weekly at 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

Intermediate Designer: Unicorn Wanted, Salary Missing

Paul Austin-Menear and Jennifer Houle — Fri, 06 Feb 2026 08:02:00 GMT

A global “social-first” agency posts a Toronto designer role that reads like a nightclub flyer: passport program, dogs in-office, celeb gossip, and “ideas worth talking about.” Jen and Paul dig into what’s real, what’s fluff, and what’s quietly doing wage suppression work... including a unicorn skill list (typography and motion and AI prompting) and the big missing piece: the salary range… in Ontario… right after pay-transparency rules kicked in.

They also get into the ethics of interview “extra credit,” why agencies can be a pressure cooker, and how culture-forward language can be both a magnet and a filter.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-004-unicorn-wanted-salary-missing

Jen and Paul roast weekly at 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

eCommerce Specialist: The Cafeteria Conspiracy

Paul Austin-Menear and Jennifer Houle — Fri, 30 Jan 2026 08:02:00 GMT

This week, Paul brings the post... and Jen gets to sit back with the matches. They roast an eCommerce Specialist role that’s oddly vague where it matters (reporting structure, authority, pay), but wildly specific where it hurts (ownership-heavy responsibilities, budget allocation, performance diagnostics, and retail partner sellout targets… in a “specialist” title). Along the way : the strange perk of “discounted or free food,” the real-world problem with salary expectation questions, and why job postings reveal culture before you ever meet a hiring manager.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-003-the-cafeteria-conspiracy

Jen and Paul roast weekly at 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

Executive Assistant & Office Manager: Two Jobs in a Trench Coat

Paul Austin-Menear and Jennifer Houle — Fri, 23 Jan 2026 08:01:00 GMT

This week Jen drops a deceptively “cool mission” job post: executive assistant and office manager at a polar expedition travel company… and the bullets just keep coming. Calendar wrangling for the president plus five other execs, expenses, decks, events, vendors, fridge clean-outs, building access, and even health & safety committee work—paired with “flexible hybrid,” 10 vacation days, and no salary range. Jen and Paul dig into what this posting signals about org design, hidden workload, gender-coded expectations, and why “discretion” shows up like a warning label.

If you’ve ever wondered how to read between the lines of a job post (or how employers accidentally advertise churn), this roast is for you.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-002-two-jobs-in-a-trench-coat

Jen and Paul roast weekly at 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

Marketing Coordinator, Apparently.

Paul Austin-Menear and Jennifer Houle — Fri, 16 Jan 2026 20:01:02 GMT

A “basic” Marketing Coordinator posting walks into Roast the Post… and quietly gives away everything about the company behind it. In this episode, Jen and Paul peel back the bullet points to decode what support, liaison, fast-paced, and PowerPoint proficiency really mean when you’re the one expected to keep samples moving, approvals flowing, and everyone else out of trouble. From acronym soup and herding cats to salary signals and missing mentorship clues, this roast isn’t about dunking... it’s about learning how job posts reveal culture, chaos, and credibility if you know how to read them. Whether you’re applying, hiring, or just trying to make sense of the madness, this one will sharpen your decoder ring.

Full job ad and notes for job-seekers and hiring managers here : https://roastthepost.substack.com/p/ep-001-coordinator-apparently

Jen and Paul roast weekly at 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