Let’s Roast.
Ever dreamed of turning your hobby into a six-figure salary? This week’s job ad offers just that… for the right (or wrong) candidate. A wealthy family is hiring a full-time golf companion to travel between Toronto and Singapore, blending coaching, cultural immersion, and a healthy dose of ambiguity. Is this the ultimate gig for a new grad with a finance degree and a love of the links, or a trap disguised as a dream job? Buckle up, this roast is about to take a swing at the 1%.
Follow along with the full job ad here:
The Bigger Picture
How do you design a role that bridges cultural gaps, professional ambitions, and personal lifestyle… without turning into a logistical disaster or a short-term gimmick? This job ad isn’t seeking a golf companion, it’s seeking a golf companion AND…
Clearly communicating the AND is the key to success or failure.
At a Glance: The Job Profile
Job Title: Golf Companion
Report-to Title: Unknown
Company Size: Unknown
Industry: Family Office
What do they do?: Things. They do things. Presumably. The details of which are murky at best.
Head Office Location: Toronto, ON, Canada
Job Location: Toronto, ON, Canada & Singapore
Geographical Operating Area: Unknown
Job Type: Permanent, Full-Time, On-Site
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:
Is this role a stepping stone or a dead end? How will this experience translate to my long-term career goals?
What’s the real scope of the job? Am I just a golf coach, or am I expected to be a cultural liaison, chauffeur, or even a business advisor?
How are travel, housing, and visas handled? Will I be stranded in Singapore with no support?
What’s the family’s background? Are they legitimate, or is this a front for something shadier?
Is the salary worth the lifestyle? Can I afford to maintain a home base while traveling 75% of the time?
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:
Issues
Ambiguity in Role Design: The job blends golf coaching, cultural tutoring, and potential business advising without clear boundaries, leading to confusion for candidates.
Lack of Logistical Clarity: No details on travel arrangements, housing, visas, or insurance, which could deter qualified applicants.
Unrealistic Sustainability: The role’s demands (75% travel, no roots) make it unsustainable long-term, risking high turnover.
Trust Gaps: The ad’s vagueness and lack of credibility (e.g., no company details) may raise red flags for candidates about legitimacy or safety.
Fixes
Define the Role Clearly: Separate the golf coaching from cultural/business advisory duties, or explicitly state the blend.
Clarify Logistics: Specify who covers travel, housing, visas, and whether a vehicle is provided (or required).
Address Sustainability: Offer a fixed-term contract (e.g., 2 years) to attract candidates who see it as a temporary adventure.
Build Trust: Include details about the family office’s background, interview process, and support systems (e.g., health insurance, relocation assistance).
The Verdict
Jennifer Houle:
7 / 10 (Job Ad)
5 / 10 (Role Design)
The job ad was pretty clear, though it was missing some important points of clarity. The role design isn’t very sustainable, but maybe that’s okay. This doesn’t strike me as one that would have a long-term employee.
Paul Austin-Menear:
6 / 10 (Job Ad)
6 / 10 (Role Design)
It was just OK, from my perspective. There are certainly some endemic trust issues and the employer is a black box. That will be tough to navigate. This could be a dream job for a new grad, or it could be a nightmare. The devil’s in the details.
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 contributions made on Buy Me a Coffee to help pay for our production costs, and donate anything raised beyond our costs to charity.
