Let’s Roast.
What happens when your job is to say “no” to the people whose job is to say “yes”? This week, Paul and Jen tackle a Director of Compliance Operations role where the reporting structure is a minefield, the salary is a sick joke, and the expectations are sky-high. For job seekers, this is a cautionary tale about the cost of ethical tension. For hiring managers, it’s a blueprint for how not to design a critical role. Listen in to find out why this job ad is a case study in systemic dysfunction… and why the best candidates will run the other way.
Follow along with the full job ad here :
The Bigger Picture
How do you design a compliance role that actually works? This episode isn’t just about roasting a job ad… it’s about the fundamental tension between profit and principle in financial services. The real question: Can a role like this ever succeed when its structure guarantees conflict? For organizations, the answer lies in clarity, authority, and compensation that reflects the true value (and risk) of the work.
At a Glance: The Job Profile
Job Title: Director, Compliance Operations
Report-to Title: CCO & CAMLO (dual-reporting)
Company Size: 1,001 - 5,000
Industry: Financial Services
What do they do?: Personal loans, Home Improvement Loans, Debt Consolidation, Mortgage, Consumer Financing, Automobile Financing, and Retail point-of-sale Financing
Head Office Location: Montreal, QC, Canada
Job Location: Toronto, ON, Canada
Geographical Operating Area: Canada
Job Type: Full-Time, Permanent (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:
How will I navigate conflicting directives from two bosses with opposing goals?
What does “entrepreneurial” mean in a compliance role, and is that a red flag for a role that exists to mitigate risk?
How many people am I actually managing, and what support will I have?
Is there a progression path here, or is this a dead-end role?
How is the performance bonus calculated, and what metrics am I being judged on?
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:
Dual reporting creates paralysis: Without clear final decision-making authority, the role is set up for gridlock, especially when commercial and compliance goals clash.
Ambiguous acronyms and responsibilities: Unclear language (CCO = Chief Commercial Officer or Chief Compliance Officer?) and vague tech/people management expectations risk attracting the wrong candidates, or scaring off the right ones.
Salary misalignment: A $120K–$150K range for a high-stakes, high-responsibility role in Toronto is under-market and signals undervaluation of risk mitigation.
No career progression: The lack of intermediate roles between Director and C-suite means top talent will stagnate or leave.
Fixes:
Clarify the reporting structure: Assign a single final decision-maker to resolve conflicts and streamline accountability.
Define “entrepreneurial” in compliance: Replace buzzwords with concrete expectations—compliance requires rigor, not risk-taking.
Adjust compensation: Benchmark against industry standards for similar roles in high-cost cities, and tie bonuses to measurable risk mitigation outcomes.
Add career ladders: Create senior director or VP-level roles to give high performers a path forward.
The Verdict
Jennifer Houle:
8 / 10 (Job Ad)
5 / 10 (Role Design)
The job ad was nicely structured, and contains a lot of information. They included a salary range and mandatory disclosures, unlike many organizations. The role design is a different story though… poorly thought through, with an ambiguous reporting structure and nightmarish power dynamics. This person will burn out because of how the role was designed.
Paul Austin-Menear:
7 / 10 (Job Ad)
5 / 10 (Role Design)
The job advert itself was easy to navigate and contained all of the information I’d need to decide if I was going to apply. So, good marks there—though I took a few points off for including irrelevant information and perks that wouldn’t apply to the successful candidate. The role design was a struggle. This person will be stretched thin, and won’t be properly compensated for the importance of their work in relation to the value it creates for the org.
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.
