Roast the Post Podcast

What happens when a national security AI startup writes a job ad entirely in spy-movie trailer voice? Jen and Paul find out, with backup from a very special guest: Rebecca Wicker, aka The Strategic Linguist, who knows exactly what words like "faceless," "borderless," and "adversary" are doing to your brain while you read them. The mission, should you choose to accept it: a business operations hire...

One tiny Stockholm startup, 2.6 million Euros raised, a 13 million Euro letter of intent, an ex-McKinsey founder, a NATO accelerator, and a Founder's Associate role that promises "the steepest learning curve I can offer" ... in exchange for what the ad itself admits is "full ownership of you." This week Jen and Paul head to Sweden to figure out whether this is radical hiring transparency or the mo...

Paul and Jen dissect the viral headline claiming Gen Z's iced coffee habit in job interviews could be costing them jobs, after a corporate recruiter with 16 years of experience warned that candidates arriving with lattes appear "too casual" in buttoned-up Fortune 500 environments. The hosts unpack the recruiter's advice... "finish the coffee before you walk in"... and ask whether an iced coffee re...

Dive into the choppy waters of a Chief Steward job ad that’s equal parts intriguing and infuriating. Jen and Paul dissect a role that’s supposed to be the backbone of ferry operations but reads like a last-minute scramble of responsibilities, questionable qualifications, and a salary range that leaves more questions than answers. Is this a dream job for maritime multitaskers or a sinking ship of u...

Ever wondered if you could turn your love for sports cards into a full-blown career? This week, Jen and Paul tackle a job ad that claims you can do just that... as a "Sports Card Breaker." But is this the dream gig for hobbyists, or just another example of modern career chaos? From live-streaming unboxings to coordinating shipping logistics, this role blends entertainment, e-commerce, and a dash o...

This week on Roast the Post , Jen, Paul, and special guest Brandi Copeland dive into a Director of HR job ad that’s equal parts baffling and infuriating. The posting doesn’t just describe a role... it demands total cultural submission, with a side order of impossible expectations. Think "influence without authority," a CEO who’s also the Chief Purpose Officer (because why not?), and a laundry list...

This week, Jen and Paul dissect two pressing workplace issues: WestJet flight attendants challenging the definition of paid work and the rise of AI governance in collective bargaining agreements. This episode explores the fairness of unpaid labour, such as pre-flight safety checks, and discusses whether AI regulation should be led by governments or collective agreements. Key discussion points incl...

Ever wondered what it’s like to be a digital detective for the auto financing world? This week on Roast the Post , Jen and Paul dive into the shadowy, screen-bound life of a Skip Tracer ... a role that’s part investigator, part debt collector, and 100% intriguing. From Boolean searches to social media stalking (the legal kind, of course), this job ad promises a caseload of 50-100 files and the thr...

Jen and Paul dissect the headline “Chime to cut 10% of total workforce on AI driven efficiencies” With Chime reducing approximately 10% of its workforce citing AI-enabled efficiencies, the episode asks: when AI creates productivity gains, what should organizations optimize first... profits, employee capacity, customer experience, innovation, or shorter work weeks? The discussion challenges the eth...

This week, Jen and Paul tackle a job ad for a Strategy & Ops Leader role at an AI-driven investment management firm working with firms managing over $10 trillion in assets. The ad oozes confidence... boasting about revolutionizing the industry, assembling the "most talent-dense startup in New York," and offering perks like free meals, gym stipends, and a stunning office. But beneath the bravado, t...

This week on Roast the Post , Jen interviews co-host Paul, revealing his unconventional career path through the national intelligence service recruiting pool to entrepreneurship and management consulting. They discuss the origins of their podcast, their shared frustration with the atrophying labour market, and the importance of having human-driven systems that are amplified by technology (and not...

Ever fantasized about swapping maple syrup for Vegemite and trading Toronto’s Bay Street for Sydney’s harbourfront? This week, Jen and Paul roast a job ad that’s equal parts travel brochure and sales pitch, offering a one-way ticket to a stockbroking career "Down Under"... complete with sponsorship, cold calls, and a clear... ish... path to promotion. If you can stomach the grind, that is. But wit...

Ever wondered what a job ad reveals about a company’s culture, expectations, and potential red flags? This week, Paul, Jen, and special guest Jonny Havey... founder of eLearning Partners... dive into a Learning Experience Designer role that’s equal parts intriguing and overwhelming. From employer branding that hits the mark to responsibilities that blur the lines between design, strategy, and proj...

This week on Roast the Post , Paul interviews co-host Jen, revealing her unconventional career path from struggling with traditional education to thriving in human resources. They discuss the origins of their podcast, their shared frustration with opaque job ads, and the importance of transparency and authenticity in hiring. Jen’s story highlights the value of being seen in your career and why job...

This week, Jen and Paul tackle a job posting for a Head of YouTube role at an ed-tech company that’s equal parts inspiring and infuriating. The hosts praise the company’s mission and employer branding but skewer the vague reporting structure, the unrealistic expectations of “obsessed” candidates, and the glaring omission of salary details. They also question whether the role is more about marketin...

Ever wonder what happens when a job ad is so vague, it might as well be written in invisible ink? This week on Roast the Post , Jen and Paul tackle a Founding BizOps Lead role at a "stealth VC-backed legal AI startup"... where the company name, mission, and even the hiring process are shrouded in mystery. Your first interview? With an AI named Jack. The perks? "Massive career acceleration" (transl...

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...