Roast the Post Podcast

Ever wonder what happens when a job ad tries way too hard to sound fun and accidentally leaks entitled toxicity all over the lobby floor? This week on Roast the Post , Jen and Paul eviscerate a wealth management firm’s posting for a “Director of First Impressions”... a role that’s equal parts receptionist, placeholder for pretty privilege, and a potential HR nightmare. From gender-coded language (...

Dive into the chaos of a job ad that can’t decide if it’s hiring a construction scheduler or a project manager for Toronto Pearson Airport’s multi-billion-dollar infrastructure overhaul. Jen and Paul dissect the confusing responsibilities, missing salary, and baffling lack of transparency in this high-stakes role. Is this a case of corporate laziness, a sneaky cost-cutting tactic, or just a job ad...

Ever seen a job title so whimsical it makes you do a double-take? This week on Roast the Post , Jen and Paul tackle the "Happiness Engineer" role... a position that sounds like it belongs in a corporate parody but packs a punch with its focus on customer experience, technical problem-solving, and even AI fluency. Is this the future of customer support, or just a clever rebrand of a classic role? W...

Ever dreamed of being the security mastermind behind a global football tournament? This week, Jen and Paul roast a baffling job ad for a Senior Security Manager role that’s as temporary as a red card. The catch? You’re expected to oversee non-competition venues (think: team hotels, training sites) for a three-week gig ... with all the responsibility and none of the clarity. The ad demands a decade...

Jen is based in Victoria, Canada. Paul is based in Toronto, Canada. That’s about 3,500km in distance, as the crow flies. Needless to say, they’re almost never in the same place at the same time. Something really cool happened on April 29th though—the stars aligned, and they were in the same city. So? Well, they got together at a pub and held their first ever livestream event—Roast the Post: Happy...

Ever seen a job ad that feels like it was written by a time traveler? This week on Roast the Post , we dissect a Communications Associate role for a nonprofit preserving Revolutionary War battlefields in the United States... where the biggest twist isn’t the history, but the ban on social media . That’s right: no tweets, no posts, just… print ads and event logistics? Jen, Paul, and guest roaster K...

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...

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 s...

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 p...

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 laugh...

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 "tr...

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 benefi...

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, i...

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...

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 f...

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-an...

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 car...

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...

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 humani...

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...

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/standin...

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 whet...

“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 in...

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 compan...

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 d...