Roast the Post Podcast

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...

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 Onta...

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 per...

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 sala...

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...