Let’s Roast.
Ryan from Peterborough, Canada sent in a “Chief of Staff” role that accidentally confesses the entire company is held together with duct tape and grand ambition. If you’ve ever wondered whether a job ad is warning you away… well, this one isn’t subtle.
Follow along with the full job ad here :
The Bigger Picture
What happens when a company uses a prestigious title to paper over an undefined operating system… then asks one hire to become the operating system? This isn’t about dunking on a posting; it’s about job design as risk management for both the business and the human doing the work.
At a Glance: The Job Profile
Job Title: Chief of Staff
Report-to Title: Founder
Company Size: 11-50
Industry: Investment Management
What do they do?: Facilitate acquisitions of and investments in small businesses throughout North America.
Head Office Location: New York, NY, United States
Job Location: Remote (North America)
Geographical Operating Area: North America
Job Type: Full-Time, Permanent (Remote)
For the Job Seekers
Did you come across a job ad like this? These questions might help you shed some light on what working there is really like:
When they say “intentionally broad and demanding,” what work are they explicitly not resourcing elsewhere… and why?
What decisions do I have authority to make without escalation, and what budget/tools do I control?
Who owns each function today (hiring, sales ops, product, investor relations), and what breaks if I don’t “fix” it?
What does “performance-based upside” mean in writing: metrics, timing, payout, and who decides?
What does success look like at 30/60/90 days, and what tradeoffs are acceptable if everything can’t be done?
What guardrails exist for workload: prioritization rules, off-hours expectations, and coverage when I’m away?
Why is a Loom video required up front, and how do they mitigate bias in screening?
For the Job-Seeker Seekers
Are you writing a job ad for a similar role? Consider these hidden issues that might impact the success of your recruitment campaign:
Outcome: You’ll attract “hero” candidates and repel steady operators; retention risk skyrockets. Fix: Narrow scope into 1–2 outcomes, define decision rights, and staff the rest (or explicitly defer it).
Outcome: Title inflation (“Chief of Staff” as COO/recruiter/product/sales ops) creates internal conflict and external confusion.
Fix: Re-title the role (Ops Lead/COO/Business Operations) or split into two hires with clean interfaces.
Outcome: “Move without permission” + no policies/process = inconsistent decisions, compliance risk, and stakeholder blowback.
Fix: Establish clear escalation lanes, guardrails, and a simple operating cadence (weekly priorities, decision log).
Outcome: No salary range + vague upside = low-quality applicant pool or prolonged vacancy.
Fix: Publish a credible range, define upside mechanics, and state what “competitive” means for the market.
Outcome: Up-front Loom video increases bias and excludes strong candidates (accessibility, neurodiversity, privacy).
Fix: Start with structured questions or a short work sample; offer alternatives and score with a rubric.
Outcome: The “pressure cooker” promise becomes a burnout factory and damages employer brand.
Fix: Pair intensity with sustainability: realistic workload, backup coverage, benefits, and explicit boundaries.
The Verdict
Jennifer Houle: 0 / 10
This job is a crime against humanity. I would give it negative points if I could. I need a hot shower to wash the ick off.
Paul Austin-Menear: 6 / 10
I looked at the job ad and the job’s role design separately. The role design sucks… they want a unicorn, without saying how much they’re willing to pay. That person will burn out right quick. The job ad though… it was honest. It was well-structured. There was a lot about it that I didn’t like… but it was a bit refreshing.
Roast the Post is a passion project of Jen Houle and Paul Austin-Menear. The show helps job-seekers and employers get dud job ads out of their lives. We use these one-time, any-amount contributions to help pay for our production costs, and donate anything raised beyond our costs to charity.
