Roast the Post Podcast

Strategy & Ops Leader: The Wolf of West Village

Paul Austin-Menear — Fri, 28 Aug 2026 07:09:52 GMT

Let’s Roast.

This isn’t just a job ad, it’s a high-stakes gamble. A Strategy & Ops Leader role at an AI-powered investment firm promises to "build the future of investment management," but the fine print reveals a company caught between ambition and chaos. With a salary range that’s as confusing as the role itself, and perks that scream "live at the office," this ad forces both job seekers and employers to ask: How much ambiguity is too much? And more importantly… who’s actually in charge here?

Follow along with the full job ad here:

SEE JOB AD

The Bigger Picture

How do we design roles that balance ambition with clarity, especially when the stakes are $10 trillion and the expectations are "unreasonably high"? This episode isn’t just about roasting a job ad; it’s about the tension between innovation and the need for structure, trust, and sustainability in high-growth environments.

At a Glance: The Roasty Profile

Job Title: Strategy & Ops Leader
Report-to Title: Unknown
Company Size: 51-200 employees
Industry: Financial Services
What do they do?: AI operating system for investment management, built for the world’s largest wealth firms and fintechs. This Company works with firms managing more than $10 trillion in client assets
Head Office Location: New York, New York, USA
Job Location: New York, New York
Geographical Operating Area: Unknown
Job Type: 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:

If the role promises “career acceleration” but lacks clear responsibilities, how do I assess whether this is growth or exploitation?
The ad emphasizes “exceptional” talent… how do I know if I fit their undefined standard, or if it’s just a buzzword?
With no clear reporting structure, how do I evaluate the authority and impact of this role?
The company boasts about its clients managing $10 trillion… how do I verify these claims and assess the company’s stability? Having big clients doesn’t mean that this company is financially sound.
Free meals and gym stipends sound great, but what does a “five days a week in-office” requirement signal about work-life balance?

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 Created

Lack of Role Clarity: A vague job description risks attracting unqualified candidates or overwhelming the right ones. Outcome: High turnover, misaligned expectations. Fix: Define core responsibilities and success metrics upfront.
Overemphasis on “Exceptional” Talent: Without clear criteria, this signals elitism and may deter diverse applicants. Outcome: Homogeneous, potentially toxic culture. Fix: Replace subjective terms with specific skills and cultural values.
Unsustainable Work Expectations: Perks like free meals and in-office mandates imply long hours. Outcome: Burnout, low retention. Fix: Offer flexibility and transparent work-life boundaries.
Salary Range Ambiguity: A $160K–$230K spread without justification creates inequity. Outcome: Resentment, perceived unfairness. Fix: Tie compensation to objective benchmarks (e.g., experience, impact).
Cultural Red Flags: Phrases like “no tolerance for brilliant jerks” may clash with finance/startup norms. Outcome: Misaligned hires, cultural friction. Fix: Audit language for inclusivity and authenticity.

The Verdict

Paul Austin-Menear

6 / 10 (Job Ad)
0 / 10 (Role Design)

The job ad is persuasive and honest. Unfortunately, the honesty is about how ridiculous the expectations and structure are. The role design is… nonexistent. Whomever is hiring for this role doesn’t know what they want or need, and is hoping that a magical being made from perfection dust will teleport in to save them from themselves.

Jennifer Houle

7 / 10 (Job Ad)
0 / 10 (Role Design)

They knew who they wanted, and they wrote the job d very specifically and painstakingly to find that person. I’ll give them credit for that, despite the mixed signals (and not-so-subtle cues that are problematic). The role design is a hot mess though. It’s not sustainable. It’s not even understandable. Big, fat, smelly zero.

Live Studio Audience (Average Score)

4 / 10 (Job Ad)
4 / 10 (Role Design)

Have Your Say!

What did you think about this job ad and role design? Now’s the time to put on your Roast the Post Podcast judge’s hat and weigh in. Leave a rating for the job ad, and a rating for the role design here :

VOTE NOW

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Support the Show

Roast the Post is a passion project of Jennifer Houle and Paul Austin-Menear. The show helps job-seekers and employers get dud job ads out of their lives. There are several ways that you can help us on our mission to unf*ck the hiring process…

1 —> Share this episode with someone who’d like it.

2 —> Pick up a copy of our new e-Book, the Job Description Decoder and leave a review. The price is pay-what-you-can (even free), and all proceeds will be donated equally to Ronald McDonald House BC & Yukon, and the Toronto Humane Society.

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Hi, I'm Paul: Getting to Know Paul Austin-Menear

Paul Austin-Menear — Fri, 21 Aug 2026 07:12:39 GMT

Let’s Not Roast.

This week on Roast the Post, the tables turn as Jen interviews co-host Paul Austin-Menear, offering listeners an intimate look at the man behind the mic. Unlike their usual episodes dissecting job ads, this conversation peels back the layers of Paul’s unconventional career journey… from his rural Ontario roots to his early aspirations in the national security apparatus, his pivot to entrepreneurship, and his eventual focus on management consulting. His path is a testament to adaptability, critical thinking, and the value of soft skills in a rapidly changing professional landscape.

Paul’s career hasn’t been without its twists. He recounts the highs of building and selling a business, the lows of toxic work environments, and the lessons learned from failure… particularly the pitfalls of perfectionism. His insights into organizational design and systems thinking reveal a deep-seated belief: companies often overlook the institutional knowledge of their workforce, treating people as interchangeable parts rather than the dynamic, malleable assets they are. This perspective fuels his passion for Roast the Post, where he and Jen challenge the norms of hiring practices and advocate for transparency, humanity, and critical thinking in the workplace.

The episode also explores Paul’s vision for the future, both for himself and for Roast the Post. If given the chance to start over, he’d dive into alternative energy, driven by a fascination with sustainability and decarbonization. But for now, he’s content to use the podcast as a platform to push for better hiring practices, better leadership, and a workplace culture that values people as more than just cogs in a machine. His hope? That Roast the Post will inspire listeners to preserve the humanity in their work and resist processes that stifle individuality.

For Paul, hosting the show has been eye-opening. It’s confirmed that the dysfunctions he’s encountered in his career aren’t isolated incidents, they’re systemic. But rather than despair, he finds comfort in knowing he’s not alone. And for listeners, this episode is a reminder that career paths don’t have to be linear, that failure can be a teacher, and that the best work often comes from challenging the status quo.

Tune in for a conversation that’s as much about the people behind the podcast as it is about the problems they’re trying to solve. It’s a discussion that might just change how you think about your own career… and the next job ad you write or apply to.

Also make sure to check out ’s Substack, Pattern of Play… it’s a personal favourite in Jen’s subscription list.

Support the Show

1 —> Share this episode with someone who’d like it.

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3 —> Send us a one-time or recurring tip on Buy Me a Coffee. This helps pay for our production costs.

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Entry-Level Stockbroker: Vegemite and Volatility

Paul Austin-Menear — Fri, 14 Aug 2026 07:07:03 GMT

Let’s Roast.

Want to trade your routine for a harbourfront view and a shot at the ASX? This job ad promises a career in Sydney’s financial markets—sponsorship included—but the fine print reveals a high-stakes hustle. With a base salary that barely covers rent and a commission structure that demands you "crush it" to survive, this role is less about finance and more about sales. Is it a dream opportunity or a one-way ticket to burnout?

Follow along with the full job ad here:

SEE JOB AD

The Bigger Picture

How do you design a role that attracts ambitious talent while ensuring sustainability and fairness? This job ad highlights the tension between scalability and exploitation in sales-driven industries, challenging organizations to balance hunger for results with ethical role design.

At a Glance: The Roasty Profile

Job Title: Move to Sydney: Entry-Level Stockbroker Opportunity with Sponsorship!
Report-to Title: Unknown
Company Size: Unknown
Industry: Financial Services
What do they do?: Trade in regulated securities and financial products, primarily on the Australian Stock Exchange (ASX).
Head Office Location: Sydney, NSW, Australia
Job Location: Sydney, NSW, Australia
Geographical Operating Area: Australia
Job Type: Full-Time, Permanent

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 the base salary livable in the location, or am I being set up for financial strain?
What’s the real cost of relocation, and does the sponsorship cover it?
How achievable is the RG146 certification, and what support is provided?
What’s the turnover rate for this role, and why?
Am I comfortable with a role that’s heavily commission-based?

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: High turnover due to unsustainable base salary, leading to constant recruitment costs and lost productivity. Fix: Offer a living wage to improve retention and reduce turnover costs. Clearly outline career progression and support structures to attract serious candidates.
Outcome: Misalignment between role expectations (sales) and title (stockbroker), leading to dissatisfaction. Fix: Rename the role to reflect its sales nature and clarify responsibilities to manage expectations.
Outcome: Lack of cultural fit due to vague descriptions of workplace environment. Fix: Include cultural and inclusivity statements to attract candidates who align with the organization’s values.

The Verdict

Jennifer Houle

7 / 10 (Job Ad)
6 / 10 (Role Design)

The job ad was persuasive, and really leaned on emotional hooks. Manipulative? Maybe. But, effective? Yeah. And if this is a recruitment agency writing and posting the ad, I get it. The role design was a bit ambiguous. There isn’t much of evidence of a supporting organization that focuses on professional growth, and the salary is brutal for the work location.

Paul Austin-Menear

8 / 10 (Job Ad)
5 / 10 (Role Design)

The job was quite good, albeit shy on some of the details that I’d normally want to see. Could I see some starry-eyed twenty-something reading this job and getting excited? Absolutely. The role design sucks though, centred around the lack of a living wage. There’s a case to be made for “keep ‘em hungry”, but this is too extreme. All that it will do is fuel turnover for this role, which will increase the firm’s hiring costs. I’m pretty certain there could have been an equilibrium point where a higher base salary to start would be offset by the lower recruitment costs gained from retention over time.

Have Your Say!

VOTE NOW

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Support the Show

1 —> Share this episode with someone who’d like it.

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Learning Experience Designer: Unsupervised Hiring, with Jonny Havey

Paul Austin-Menear — Fri, 07 Aug 2026 07:10:24 GMT

Let’s Roast.

Think a job ad can’t be both brilliant and baffling? Think again. This week’s roast features a Learning Experience Designer role that excels at employer branding, but soon stumbles into a maze of contradictions. With Jonny Havey’s expert insights, we explore how a job posting can promise autonomy and creativity… while demanding enough hats to outfit an entire team. Whether you’re a job seeker decoding the fine print or a hiring manager crafting your next ad, this episode is a masterclass in reading between the lines.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a role that balances creativity, strategy, and execution without collapsing under the weight of its own expectations? This episode challenges the notion that more responsibilities equal more value, making a case that clarity and focus are the real keys to sustainable job design.

At a Glance: The Job Profile

Job Title: Learning Experience Designer
Report-to Title: Unknown
Company Size: 11 - 50
Industry: eLearning
What do they do?: A learning and development consultancy that helps organizations design custom training programs, eLearning, onboarding, learning experiences, and training videos to improve employee performance and organizational capability.
Head Office Location: Milton, ON, Canada
Job Location: Remote, Canada
Geographical Operating Area: Unknown
Job Type: Full-Time, Contract

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:

Does this role truly offer the autonomy and creativity it promises, or is it a bait-and-switch?
How will the lack of clarity around reporting structure and team size impact my day-to-day experience?
Are the qualifications realistic, or are they a wishlist that no single candidate could fulfill?
What does the emphasis on “rapid writing” and “fast-paced environment” signal about the company’s expectations for workload and work-life balance?
If the role involves client-facing work, why isn’t that explicitly stated in the responsibilities?

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:

Outcomes of the Issues

Misaligned Expectations: Candidates may apply expecting a focused design role but find themselves overwhelmed by project management and strategic duties, leading to high turnover.
Legal Risks: The contract structure and defined work hours could legally classify the role as employment, exposing the company to liability for benefits and severance.
Talent Shortage: The overly broad qualifications and responsibilities may deter qualified candidates, leaving the role unfilled or filled by someone underqualified.
Cultural Misrepresentation: The ad’s emphasis on fun and flexibility may clash with the reality of a high-pressure, multi-functional role, eroding trust and employer branding.

Suggested Fixes

Clarify the Role: Split the responsibilities into distinct roles (e.g., Learning Experience Designer, Project Manager, Strategist) to attract candidates with the right expertise.
Adjust the Title: Rename the role to reflect its true scope (e.g., “Fractional Chief Learning Officer” or “Senior Learning Strategist”) to align with expectations and compensation.
Define the Team: Clearly state the reporting structure, team size, and whether the role is client-facing to set realistic expectations.
Comply with Labor Laws: Either remove fixed work hours from the contract ad or reclassify the role as full-time employment to avoid legal risks.
Simplify Qualifications: Focus on core, non-negotiable skills and separate soft skills (e.g., collaboration, communication) from technical requirements to avoid overwhelming candidates.

The Verdict

Jonny Havey

3 / 10 (Job Ad)
1 / 10 (Role Design)

The job ad was well-written, until it wasn’t. The role design would have been pretty good… except that it didn’t reflect what a Learning Experience Designer actually does. I really feel like they were trying to get a more experienced professional at a discount by sneaking some things in.

Paul Austin-Menear

4 / 10 (Job Ad)
3 / 10 (Role Design)

The job ad had some great elements of employer branding… it told a story that was compelling. But it ended on a confusing note, leaving me wondering what happened. Did they get distracted and just hit the button? As for the role design… dumpster fire. This poor soul will bounce out after a few months, and they’ll be back to square one.

Jennifer Houle

3.5 / 10 (Job Ad)
2 / 10 (Role Design)

They put pen to paper, and started the job ad out pretty well. Too bad they lost focus and took a nap instead of finishing strong. The role design? Well, we taped this on a Thursday so why not give them a two? What they wrote down made just as much sense.

About the Guest

Jonny Havey is the founder of eLearning Partners, a business consultant, and former CPA and IT auditor at PwC. He partners with forward-thinking business owners and teams within S&P 500 companies to identify and eliminate hidden profit leaks by turning education into a competitive advantage.

Through his work, Jonny helps organizations increase product adoption, improve customer and employee retention, and drive measurable profit growth. His approach focuses on closing the gap between what businesses are doing, what customers and employees actually need, and what creates real, lasting results.

Support the Show

1 —> Share this episode with someone who’d like it.

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3 —> Send us a one-time or recurring tip on Buy Me a Coffee. This helps pay for our production costs.

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Hi, I'm Jen: Getting to Know Jennifer Houle

Paul Austin-Menear — Fri, 31 Jul 2026 07:04:54 GMT

Let’s Not Roast.

This week’s episode of Roast the Post breaks from the usual format. Instead of dissecting another spicy job ad, Paul sits down with co-host Jen for a personal interview, offering listeners a rare glimpse into the mind and background of the person who’s been roasting job ads alongside him for months.

Jen’s career journey is anything but linear. She recounts her early struggles with traditional education, struggles with conventional authority, and how she navigated a series of unconnected pursuits… from yoga instructor to office manager… before finding her footing in human resources. It was there, under the mentorship of a perceptive leader, that she first felt truly seen and valued for her skills. This experience became a turning point, shaping her passion for transparency, fairness, and calling out the often absurd expectations embedded in job descriptions.

The conversation also revisits the origins of the Roast the Post Podcast. What started as a casual invitation to chat on another podcast quickly turned into a shared mission. Jen and Paul, initially strangers, bonded over their mutual disdain for vague, jargon-filled job ads and the systemic issues they often mask. Their chemistry was immediate, and within months, they were co-hosting a show dedicated to dissecting, and occasionally eviscerating, the worst of the worst of outdated corporate hiring practices.

Jen’s perspective is grounded in her belief that job ads should reflect reality, not aspiration. She argues that clarity and honesty in job ads aren’t just ethical, they’re practical leadership considerations. When organizations obscure the truth about roles, culture, or expectations, they risk attracting the wrong candidates and alienating the right ones. This episode dives into why that matters, not just for job seekers, but for the health of organizations as a whole.

For listeners who’ve ever felt like a square peg in a round hole, Jen’s story is a reminder that career paths don’t have to be straight lines. Her journey underscores the importance of finding environments where your strengths are recognized, and where you’re empowered to challenge the status quo. It’s a theme that resonates deeply with the ethos of Roast the Post: question the norms, demand better, and don’t settle for less than you deserve.

Tune in for an episode that’s as much about the people behind the podcast as it is about the problems they’re trying to solve. It’s a conversation that might just change how you think about your own career… and the next job ad you encounter.

Support the Show

1 —> Share this episode with someone who’d like it.

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3 —> Send us a one-time or recurring tip on Buy Me a Coffee. This helps pay for our production costs.

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Head of YouTube: The Scrappiest 'Lil YouTuber

Jennifer Houle — Fri, 24 Jul 2026 07:13:08 GMT

Let’s Roast.

Building a YouTube channel from scratch is hard. Building one for a company that doesn’t know what it wants? That’s a boss-level challenge. This week, we dissect a job post that promises creative freedom but buries the lead on who’s in charge, what the salary is, and whether “scrappy” is code for “turn water into wine.” For job seekers, it’s a cautionary tale. For hiring managers, it’s a lesson in clarity, or the lack thereof.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a role that demands both creative vision and operational rigour without setting up the hire to fail? This job post exposes the tension between artistic control and data-driven growth, forcing us to ask: Can a company truly empower a “YouTube genius” if it doesn’t fully understand what it needs?

At a Glance: The Job Profile

Job Title: Head of YouTube
Report-to Title: Unknown
Company Size: 11–50 employees
Industry: Educational Technology (EdTech) / Children’s Digital Media
What do they do?: Develop award-winning, Montessori-inspired digital toys and educational apps that encourage creativity and imaginative play for young children.
Head Office Location: Toronto, Ontario, Canada
Job Location: Toronto, Ontario, Canada
Geographical Operating Area: Global
Job Type: Full-Time, Hybrid

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:

If the reporting structure isn’t clear, how will you navigate conflicting priorities between creative vision and performance metrics?
The ad emphasizes “self-starters only”, but what happens when your autonomy clashes with the Chief Creative Officer’s expectations?
They want someone who’s grown a channel to 300K–500K subscribers. Do you have proof you can do it again… and are you prepared to give up your own successful channel for this role?
How will you balance the demand for “data-driven” decisions with the warning not to let the channel become “purely data-driven”?
The company is mom-founded and values diversity. How will you assess whether their culture matches their claims during the interview process?

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:

Shortcomings and Impact

Lack of Reporting Structure: Creates ambiguity in decision-making, leading to friction between the Head of YouTube and the Chief Creative Officer (CCO). This could result in stalled projects, misaligned priorities, and high turnover if the hire feels micromanaged or unsupported.
Unclear Expectations: The ad contradicts itself by demanding both data-driven growth and creative freedom. This could lead to hiring someone who excels at one but struggles with the other, resulting in poor performance and frustration.
No Salary Transparency: Risks losing top candidates who prioritize transparency. In a competitive market, this could prolong the hiring process and damage the company’s reputation as a fair employer.
Overemphasis on “Scrappy”: May attract candidates who thrive in chaos but lack the strategic discipline needed for long-term growth. This could lead to inconsistent content quality and missed KPIs.
Ignoring Accommodations: Fails to signal inclusivity, potentially deterring qualified candidates with disabilities or caregiving responsibilities. This limits the talent pool and reinforces exclusionary hiring practices.

Suggested Fixes

Define the Reporting Structure: Clearly state whether the role reports to the CCO, CEO, or another leader. This sets expectations for autonomy and collaboration.
Clarify the Balance: Explicitly outline how creative vision and data-driven decisions will coexist. For example: “You’ll own the creative direction, but success will be measured by [specific metrics].”
Post the Salary Range: Even if not legally required, transparency builds trust and attracts candidates who are serious about the role.
Replace “Scrappy” with Specifics: Instead of vague terms, describe the actual resources and constraints (e.g., “You’ll have a budget of X for tools and a team of Y to support you”).
Include Accommodation Language: Add a statement like, “We welcome applicants who require accommodations and will work with you to ensure a fair process.”

The Verdict

Paul Austin-Menear

8 / 10 (Job Ad)
7 / 10 (Role Design)

The job ad had a lot of personality, uncommonly, which I thought was great. I did dock points for some… oddness… in what they were communicating, but overall? Pretty good. The role design was tough to piece together. There are hints of some structural issues that will create friction, but it did appear like the organization wants this role to have significant latitude to pursue a committed strategic goal.

Jennifer Houle

7 / 10 (Job Ad)
6 / 10 (Role Design)

There were some missed opportunities in the job ad, from a communications perspective. Full credit for putting personality and care into it, but it could have been improved with a bit of team feedback and some reflection. It felt like the hiring managing wrote it on one pass and hit “publish” without giving it a second thought. The role design was pretty light on details… we know that there will be conflict. But maybe it will be manageable? Don’t know. I think that it was light on details because they don’t truly know what the role’s duties will look like, since this is the first time that they’ve had this people resource on their team.

Support the Show

1 —> Share this episode with someone who’d like it.

2 —> Pick up a copy of our new e-Book, the Job Description Decoder and leave a review. The price is pay-what-you-can, but any proceeds will be donated equally to Ronald McDonald House BC & Yukon and the Toronto Humane Society.

GET THE BOOK

3 —> Send us a one-time or recurring tip on Buy Me a Coffee. This helps pay for our production costs.

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Biz Ops Lead: Stealthy Like an Elephant

Paul Austin-Menear — Fri, 17 Jul 2026 07:08:13 GMT

Let’s Roast.

This isn’t just a job ad, it’s a Rorschach test. A Founding BizOps Lead role at a "stealth" legal AI startup promises to "transform the global practice of law," but the ad itself is so cryptic, it’s hard to tell if it’s a career launchpad or a trapdoor. With AI recruiters, vague responsibilities, and a salary range that’s "not provided," this job ad forces both job seekers and employers to ask: How much ambiguity is too much? And more importantly, who’s actually running the show here: the founders, the AI, or the chaos void in between them?

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do we design hiring processes that balance innovation with transparency, especially when AI is in the driver’s seat? This episode isn’t just about roasting a bad job ad; it’s about the tension between cutting-edge experimentation and the very human need for clarity, trust, and fairness in hiring.

At a Glance: The Roasty Profile

Job Title: Founding Biz Ops Lead at Stealth VC-backed Legal AI Startup
Report-to Title: Unknown
Company Size: 2-10 Employees
Industry: Legal Services
What do they do?: They’re lawyers, and build AI. Or maybe they’re AI lawyers. We’re unsure.
Head Office Location: Unknown
Job Location: Toronto, ON, Canada
Geographical Operating Area: Unknown
Job Type: Not Listed, but assumed Full-Time/Permanent

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:

If the company is in “stealth mode,” how do I assess its legitimacy and culture without basic details?
An AI is conducting my first interview, what does that say about the company’s values, and how should I prepare?
The role promises “massive career acceleration.” How do I distinguish between genuine growth opportunities and exploitative workloads?
The job blends finance, HR, compliance, and fundraising. How do I know if I’m qualified… or if the role is even realistic?
There’s no salary listed. Should I walk away, or is it worth asking for more info?

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 Created

Lack of Transparency: Anonymized job postings and vague descriptions can deter top talent and erode trust in your employer brand.
Misaligned Expectations: Promising “career acceleration” without clarity on responsibilities or growth paths risks attracting the wrong candidates—or burning them out.
AI Over-Reliance: Using AI recruiters (like Jack and Jill) without human oversight can lead to poorly crafted job ads, confused candidates, and a damaged reputation.
Role Design Flaws: Combining high-stakes responsibilities (finance, HR, fundraising) in a single role for a tiny team sets the hire up for failure… or at least severe burnout.
Legal and Ethical Risks: AI-driven hiring processes may inadvertently introduce bias, lack accountability, or fail to comply with labor laws.

Outcomes

Candidate Drop-Off: High-quality applicants may skip over the ad due to its ambiguity or perceived unprofessionalism.
Hiring Failures: Attracting candidates who aren’t truly qualified or who leave quickly due to misaligned expectations.
Reputational Damage: Poorly executed AI tools or stealthy postings can make your company look untrustworthy or disorganized.
Operational Chaos: A poorly defined role can lead to inefficiencies, as the hire struggles to prioritize conflicting demands.

Suggested Fixes

Clarify the Basics: Even in stealth mode, provide enough detail about the company’s mission, team size, and role expectations to build trust.
Humanize the Process: Use AI as a tool to enhance hiring, not replace human judgment. Ensure job ads are reviewed and refined by actual people.
Define the Role Realistically: Split overly broad responsibilities into multiple roles or clearly communicate the support and resources available.
Be Transparent About AI Use: If AI is involved in hiring, disclose how it’s being used and how candidates can engage with it effectively.
Offer Incentives for Risk: If the role is high-scope and high-risk, consider offering equity, mentorship, or other benefits to attract the right talent.

The Verdict

Jennifer Houle:
1 / 10 (Job Ad)
3 / 10 (Role Design)

The job ad itself? Garbage. 1 out of 10. It’s just not okay. And to top it off, the experience that they’re asking for is wildly mismatched from what’s realistic.

Paul Austin-Menear:
0.5 / 10 (Job Ad)
2 / 10 (Role Design)

The skeleton of the job ad was good. Too bad they didn’t fill it in with anything meaningful. They also “wrote” (I use the term generously) a job ad looking for an employee when they really should have been looking for a co-founder. There’s very little incentive for any less than bringing on an equity holder for this role.

Support the Show

1 —> Share this episode with someone who’d like it.

2 —> Pick up a copy of our new e-Book, the Job Description Decoder and leave a review. Proceeds will be donated equally to Ronald McDonald House BC & Yukon and the Toronto Humane Society.

GET THE BOOK

3 —> Send us a one-time or recurring tip on Buy Me a Coffee. This helps pay for our production costs.

SUPPORT THE SHOW

Director of First Impressions: Hold for Mr. Draper, Please.

Paul Austin-Menear — Fri, 10 Jul 2026 07:18:06 GMT

Let’s Roast.

What do you call a job ad that’s equal parts vague, condescending, and legally dubious? This week’s episode. A wealth management firm is hiring a “Director of First Impressions”… a role that sounds like a leadership position but is actually a receptionist gig with a side of emotional labour, gender bias, and a “work hard, play hard” culture that’s code for “we’ll own your evenings and weekends.” For job seekers, it’s a warning. For hiring managers, it’s a cautionary tale. Buckle up.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do we design job postings that reflect the actual value of administrative work… without resorting to title inflation, gender coding, or cultural red flags? This episode isn’t just a roast; it’s a challenge to rethink how we signal respect, clarity, and sustainability in hiring.

At a Glance: The Job Profile

Job Title: Director of First Impressions
Report-to Title: Unknown
Company Size: Unknown
Industry: Wealth Management
What do they do?: Wealth management firm overseeing approximately $300M in assets under management
Head Office Location: Indian Wells, CA
Job Location: Indian Wells, CA
Geographical Operating Area: Unknown
Job Type: Full-Time, In-Office

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:

If you see “Director of First Impressions,” ask: Is this a receptionist role with a fancy title, or does it come with actual leadership responsibilities and pay?
When a job ad uses terms like “bubbly” or “energetic,” ask: Are they describing the work environment, or are they filtering for a specific (and potentially discriminatory) “type”?
If the ad mentions “work hard, play hard,” ask: What does “play” actually entail, and is it mandatory? How will my work-life balance be impacted?
No salary listed? Ask: Why not? And be prepared to negotiate hard or walk away.
If the role blends administrative, sales, and event duties, ask: How will success be measured in each area? And is the compensation fair for the scope?

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 this posting creates

Legal Risks: Gender-coded language (“bubbly,” “herself”) and ageist terms (“younger office environment”) could expose the firm to discrimination lawsuits.
Title Inflation: Calling a receptionist a “Director” devalues the role, sets unrealistic expectations for candidates, and could harm their future job prospects.
Cultural Red Flags: “Work hard, play hard” signals a lack of boundaries, potential burnout, and a high risk of inappropriate behavior (e.g., mandatory socializing, harassment).
Unclear Expectations: Blending administrative, sales, and event duties without clear priorities or compensation structures leads to role confusion and employee frustration.
Missed Opportunities: Failing to list salary or industry-specific experience (e.g., finance) limits the candidate pool and signals a lack of transparency.

How to address them

Ditch the gendered/ageist language. Describe the work (e.g., “create a welcoming environment for clients”) instead of the personality (e.g., “bubbly”).
Clarify the title and scope. If it’s a receptionist role, call it that, and compensate it fairly. If it’s a hybrid role, define the split of duties and success metrics.
Ban “work hard, play hard.” Replace it with concrete benefits (e.g., “flexible hours,” “professional development budget”) that respect work-life balance.
Post the salary. Transparency builds trust and saves time for everyone.
Specify industry experience. If CRM or finance knowledge is helpful, say so…don’t assume candidates will “figure it out.”

The Verdict

Paul Austin-Menear:
4 / 10 (Job Ad)
1 / 10 (Role Design)

The job ad was okay… in the sense of spelling, grammar, and syntax, anyway. What the job ad communicated though was deeply problematic, and makes me hope that the firm’s misconduct insurance is robust. There will be a harassment lawsuit one day, for sure. The role design was idiotic… they signalled what they want, but what they want didn’t make sense. The requirements were envisioned by someone who doesn’t understand what they need or the human toll it will exact.

Jennifer Houle:
2 / 10 (Job Ad)
0 / 10 (Role Design)

The language they chose for the job ad is really telling, and I just can’t separate it from the things which were positive about the job ad, overall. It’s problematic, and discriminatory… hinting at an underlying culture that is the same. The role design basically guarantees that the person taking this role won’t have a life beyond work and colleagues. Feels a bit like indoctrination. Nasty.

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Construction Scheduler: Fuh-gantt-aboudit!

Paul Austin-Menear — Fri, 03 Jul 2026 07:13:01 GMT

Let’s Roast.

This week, we’re roasting a job ad that’s as confusing as Toronto Pearson Airport’s missing Terminal 2. A role buried in jargon, with a title that doesn’t match the responsibilities, and a salary so MIA it might as well be on a delayed flight. For job seekers, it’s a warning. For hiring managers, it’s a lesson in how not to attract talent. Buckle up, this one’s a wild ride.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

Why do organizations treat job postings as an afterthought, when they’re the first impression for both top talent and the public? This isn’t just about clarity, it’s about respect. A well-designed job ad signals a well-designed role, and a well-designed role is the foundation of a functional team. If you can’t articulate what you need, how can you expect to get it?

At a Glance: The Job Profile

Job Title: Scheduler
Report-to Title: “Your Manager”
Company Size: 10,001+ (Consortium)
Industry: Construction
What do they do?: Special-purpose consortium formed to manage major infrastructure projects at Toronto Pearson International Airport.
Head Office Location: Mississauga, ON, Canada
Job Location: Mississauga, ON, Canada
Geographical Operating Area: Mississauga, ON, Canada
Job Type: Full-Time, Unknown Duration

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:

If the job title and responsibilities don’t align, ask: “Which one is the priority—scheduling or project management? And why the discrepancy?”
No salary listed? “What’s the range for this role, and why isn’t it transparent?”
Vague reporting structure? “Who will I report to, and how does this role fit into the larger team?”
Missing benefits or perks? “What’s the full compensation package, including benefits, professional development, and work-life balance?”
High-stakes environment? “What support or resources are in place to ensure success in this role?”

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

Misaligned Title/Responsibilities: Confuses candidates and may deter qualified applicants from applying.
Lack of Transparency: No salary, benefits, or job duration creates distrust and wastes time for both parties.
Poor Role Design: Combining scheduler and project manager duties without clarity risks burnout and inefficiency.
Weak Employer Branding: Fails to sell the organization’s culture, mission, or value proposition.

Outcomes

Missed Talent: Top candidates may overlook or avoid the role due to ambiguity.
High Turnover: Unclear expectations lead to mismatched hires and quick departures.
Reputation Damage: Signals disorganization and lack of respect for candidates’ time.

Fixes

Clarify the Role: Separate scheduler and project manager duties or clearly define the hybrid expectations.
Include Salary & Benefits: Transparency builds trust and attracts serious candidates.
Define Reporting Structure: Candidates need to know their place in the hierarchy and decision-making authority.
Sell the Culture: Highlight what makes the organization unique—mission, values, growth opportunities.

The Verdict

Jennifer Houle:
2 / 10 (Job Ad)
2 / 10 (Role Design)

I’m mad at this job ad. There’s no information in it that describes to the candidate why they should apply or work for this organization. It doesn’t even list a salary, which is a legal requirement for companies of this size regulated by the Province of Ontario.

Paul Austin-Menear:
3 / 10 (Job Ad)
1 / 10 (Role Design)

Total clusterf*ck. Is this actually a Scheduler job, or is it a Project Manager job in disguise? The requirements listed out suggest the latter, but I suspect they’ll try to pay the salary of the former… because it’s lower. The bait-and-switch nature of it pisses me off.

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Happiness Engineer: CTRL + ALT + DELIGHT

Paul Austin-Menear — Fri, 26 Jun 2026 07:07:42 GMT

Let’s Roast.

What if your job was to turn someone’s worst day with a product into a moment of clarity… and maybe even joy? The "Happiness Engineer" role isn’t about forced fun or office parties; it’s a high-stakes, customer-facing gig disguised as a Silicon Valley punchline. For job seekers, it’s a chance to do meaningful work with real autonomy. For hiring managers, it’s a blueprint for how to actually value your support teams. But does the reality live up to the hype? Let’s find out.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a role that keeps customer empathy at the heart of a scaling organization, without letting it become a cost centre or a revolving door? This isn’t just a job posting; it’s a test case for whether companies can truly treat support as a strategic function, not an afterthought.

At a Glance: The Job Profile

Job Title: Happiness Engineer - Customer Support & Success
Report-to Title: Unknown
Company Size: 1,001 - 5,000 Employees
Industry: Software Development
What do they do?: They create software that helps people build websites, sell products online, and manage their digital content.
Head Office Location: San Francisco
Job Location: Remote
Geographical Operating Area: Global
Job Type: Full-Time, 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:

Self-scheduled hours sound great… but how do you ensure coverage during peak times, and what happens if my ‘ideal’ hours don’t align with customer demand?
You mention ‘high autonomy’… can you give me a real example of a time a Happiness Engineer made a decision that impacted the product or company direction without needing approval?
The role blends customer support with advocacy. How do you measure success in this role… is it ticket resolution speed, customer satisfaction scores, or something else?
You say support is a long-term career here. Can you share specific examples of Happiness Engineers who’ve grown into leadership or other departments, and what that path looked like?
Global salary ranges sound equitable, but how do you account for cost-of-living differences? For example, how does this salary compare to local market rates for similar roles?

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 Created:

Ambiguity in Scheduling: Self-scheduled hours could lead to gaps in coverage during peak times, risking customer satisfaction and operational efficiency.
- Outcome: Inconsistent support availability, frustrated customers, and potential burnout for employees covering gaps.
- Fix: Implement a hybrid model… self-scheduled within core hours, with clear expectations for coverage during high-volume periods.
Overpromising Autonomy: Claiming “high autonomy” without defining boundaries may result in employees overstepping or feeling unsupported.
- Outcome: Confusion about decision-making authority, potential conflicts with other teams, and disillusionment if autonomy is limited in practice.
- Fix: Define what autonomy looks like (e.g., process improvements, customer solutions) and where it ends (e.g., product changes require collaboration).
Vague AI Requirements: “AI fluency” is trendy but undefined, risking mismatched expectations between candidates and the role.
- Outcome: Hiring people who either over- or under-deliver on AI capabilities, leading to inefficiencies or missed opportunities.
- Fix: Specify how AI is used in the role (e.g., automating workflows, analyzing customer data) and provide examples of successful applications.
Global Salary Ranges: Paying the same USD amount globally may create inequities in purchasing power and local market competitiveness.
- Outcome: Difficulty attracting top talent in high-cost regions or overpaying in lower-cost areas, leading to retention issues or budget strain.
- Fix: Adjust salary ranges by region or clearly communicate how purchasing power parity is considered.
Lack of Structural Clarity: No reporting structure or team hierarchy is mentioned, which could lead to confusion about career paths and accountability.
- Outcome: Employees may feel adrift in a remote environment, unsure of how to grow or who to turn to for support.
- Fix: Include a brief org chart or describe the team structure (e.g., “Reports to a Customer Experience Lead, with opportunities to collaborate across product and engineering teams”).

The Verdict

Paul Austin-Menear:
9 / 10 (Job Ad)
8 / 10 (Role Design)

One of the best job ads that we’ve ever roasted. The job ad itself was detailed, struck a nice balance between employer branding and what matters for the candidate, and outlined purpose for the organization well. The role design hinted at respect and sustainability, with policies for wellness and fulfillment throughout.

Jennifer Houle:
9 / 10 (Job Ad)
8 / 10 (Role Design)

Absolutely one of the best we’ve ever roasted. If the whole thing wasn’t just window-dressing, many companies could learn from how this ad was structured and the role designed (from what we could tell). A few things were missing, but it was pretty good overall.

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Senior Security Manager: Red Card Riot, Football Edition

Paul Austin-Menear — Fri, 19 Jun 2026 07:03:48 GMT

Let’s Roast.

This isn’t just a job, it’s a three-week pressure cooker. A global football tournament needs a Senior Security Manager to guard everything but the actual games, yet the job ad reads like a Mad Libs reject. With no details on team support, established protocols, or even how you’re supposed to get around Boston’s sprawling suburbs, this role is a masterclass in how not to attract top talent. For candidates, it’s a leap of faith. For hiring managers, it’s a lesson in how vagueness breeds risk.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a high-stakes, short-term security role without creating more chaos than it prevents? This job ad exposes a critical flaw: temporary roles demand more transparency, not less. The lack of structure here isn’t just a hiring problem, it’s a safety liability. If the goal is to protect people and infrastructure, shouldn’t the job description do the same for the person taking the job?

At a Glance: The Job Profile

Job Title: Senior Security Manager
Report-to Title: Unknown
Company Size: A gajillion, but only every four years
Industry: Sporting Events
What do they do?: Global-level championship tournament for football.
Head Office Location: Zurich, Switzerland
Job Location: Boston, United States
Geographical Operating Area: Global
Job Type: Full-Time, Temporary Contract (Spring/Summer 2026

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:

What’s the actual scope? Are you managing a team, or are you a lone wolf? How many sites/venues are you responsible for?
What’s the crisis plan? Are there pre-existing protocols for emergencies, or are you expected to invent them on the fly?
What’s the reporting chain? Who do you answer to, and who answers to you? How does this role interface with competition-venue security?
What’s the real timeline? When does the role start/end? Are there expectations for pre-event planning or post-event wrap-up?
What’s the liability coverage? As a contractor, are you protected if something goes wrong? Who’s on the hook for legal/financial fallout?
What’s the logistical support? Is a vehicle provided? Are travel/accommodation costs covered for non-local hires?

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:

Outcomes of the Ad’s Flaws:

Attracts the wrong candidates: Without clarity, you’ll get applicants who are either overqualified (and will leave frustrated) or underprepared (and will fail).
Wastes time: Interviews will devolve into Q&A sessions about basics the ad should’ve covered.
Legal/operational risks: Vague requirements (e.g., no mention of background checks, vehicle access, or insurance) could lead to compliance gaps or safety oversights.
Reputation damage: A poorly designed ad signals disorganization, deterring top talent from future roles.

How to Fix It:

Partner, don’t DIY: Contract a specialized security firm with existing teams/protocols instead of hiring a solo manager to build everything from scratch.
Clarify the role’s boundaries: Define team size, reporting lines, and collaboration with other security entities (e.g., venue staff, local law enforcement).
Detail the “non-competition” scope: List the types of sites (hotels, training grounds) and their specific security needs.
Address logistics: Specify if a vehicle is required/provided, expected hours, and on-call duties.
Transparency on pay/benefits: Clarify if the per diem is net or gross, and whether contractors are responsible for their own taxes/insurance.
Highlight the “why”: Sell the once-in-a-lifetime experience—access to games, networking opportunities, or resume-boosting prestige.

The Verdict

Jennifer Houle:
5 / 10 (Job Ad)
Cannot Rate (Role Design)

Some of the basics were there for the job ad… it listed requirements and somewhat communicated the skills and background experience this person would need to be successful. But it was missing too much information to score better then a hair-pullingly aggressive “meh”. I couldn’t even rate the role design… they didn’t describe the responsibilities in any depth.

Paul Austin-Menear:
5 / 10 (Job Ad)
Cannot Rate (Role Design)

The information provided in the job ad was about as useful as a spacesuit designed for a turtle. On reflection, this really seemed like a job ad put out publicly to check a box that said “we recruited fairly” when they really had a candidate already lined up. I suspect this was an exercise in futility for anyone who applied to the job ad.

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Roast the Post: Happy Hour... Redux

Paul Austin-Menear — Fri, 12 Jun 2026 07:08:23 GMT

Let’s Roast.

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 Hour.

Thanks to everyone who submitted questions ahead of time… there were so many, they didn’t even get through them. In this episode, Jen and Paul circle back to some of the questions that didn’t get answered during the live event.

The Bigger Picture

How do we design hiring processes that respect candidates as humans, not just as resumes in a pipeline? The answer starts with transparency, reciprocity, and tearing down the power imbalances that turn job searches into psychological warfare.

Audience Questions Covered

Emma: How can I ensure I’m not just hiring for skills and experience, but also for cultural fit and long-term alignment with our mission-driven company? I want people who can execute, but also who truly believes in what we’re building. How do I balance those priorities during the interview process?
Alexei: How do I identify companies that genuinely invest in the development of new grads, rather than just using them as cheap labor? I want to find a workplace that values mentorship and long-term growth, but I’m not sure how to spot the red flags during the hiring process.
Jordan: I’m a new recruiter and I have a nightmare client whose requirements make it hard to keep candidates moving through the pipeline to the hiring point. Do you have any advice for pushing back on their requests so I can finish the job? I lose so many great candidates to slow progress…
Sierra: I work in finance and am trying to fill an empty role on my team, but I’m not getting good matches from our HR team. They work in a different office in a different city, and I feel like I’m being ignored. Do you have any advice?
Eliza: I’ve been quietly job hunting for two years with no luck, and had given up. Things turned recently and I have three good offers to choose from. It was so unexpected, I’m overwhelmed. How do I decide what to do?
Taryn: If you were writing a job ad, how would you do it?

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Communications Associate: (Musket) Smoke on the Water with Katelyn McArdle

Paul Austin-Menear — Fri, 05 Jun 2026 07:08:07 GMT

Let’s Roast.

Thanks to special guest roaster, Katelyn McArdle of Functional Authority. You can connect with her on LinkedIn here.

This isn’t just a job ad, it’s a time capsule. A nonprofit wants a Communications Associate to champion Revolutionary War battlefields in the United States… while explicitly banning them from the most powerful communications tool of the 21st century. For job seekers, it’s either a red flag or a dream gig (depending on your tolerance for irony). For hiring managers, it’s a masterclass in how not to design a modern role. Buckle up.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a communications role for the digital age while pretending the digital age doesn’t exist? This job ad forces us to ask: What happens when organizational identity (preserving history) collides with functional reality (needing modern outreach)?

The answer? A role that’s either a quirky labor of love or a cautionary tale about scope creep and cultural misalignment.

At a Glance: The Job Profile

Job Title: Communications Associate
Report-to Title: Director of Communications
Company Size: 11-50 Employees
Industry: Nonprofit Organizations
What do they do?: Acquire and preserve land and historical sites in the United States relevant to the American Revolutionary War, War of 1812, and American Civil War.
Head Office Location: Washington, DC
Job Location: Washington, DC
Geographical Operating Area: United States
Job Type: Permanent, Exempt, Hybrid

For the Job Seekers

If you’re a comms pro: Ask why social media is off-limits. Is there an agency handling it? A cultural aversion? Or just a missed opportunity?
If you love history: Does the mission excite you enough to overlook the role’s lack of creative freedom?
If you’re early-career: Where’s the growth path? This role reports directly to the Director—meaning no ladder, just a ceiling.
If you’re process-driven: Can you thrive in a role that’s heavy on logistics but light on innovation?
If you’re a writer: Are you okay with your words living in newsletters and print ads instead of viral posts?

For the Job-Seeker Seekers

Outcomes of these mistakes

Attracting the wrong candidates: You’ll get history buffs, not comms strategists—or worse, frustrated hybrids who leave fast.
Burnout: Without clear boundaries, this role risks becoming a catch-all for event planning, grant writing, and donor outreach.
Missed opportunities: Banning social media cuts off a critical channel for engaging younger audiences (who, newsflash, don’t read print ads).
Cultural clash: Demanding “entrepreneurial” energy while enforcing rigid processes will breed resentment.

How to fix it

Clarify the scope: Is this a coordinator role or a strategist role? The title and duties don’t match.
Embrace modern tools: If social media is off-limits, explain why—and redirect that energy into other innovative outreach (podcasts? Partnerships?).
Show the path: No one stays in a dead-end role forever. Outline how this position could grow.
Budget transparency: If this person is managing ad spend or donor pipelines, say how much. A $10K budget vs. a $1M budget changes everything.
Ditch the reference demand: Asking for references upfront is a red flag for candidates. Save it for the offer stage.

The Verdict

Katelyn McArdle:
5 / 10 (Job Ad)
4 / 10 (Role Design)

There was a mismatch between what the job ad communicated that the organization wants, and what it communicated that it needs. There’s some tension there, and it’s unclear at points what they truly are looking for in a Communications Associate.

Jennifer Houle:
7 / 10 (Job Ad)
4 / 10 (Role Design)

I gave them credit on the job ad—it listed a report-to, it clearly described benefits, it clearly described what they were after. The what they were after part was the problem—the role design is sorely lacking. There’s serious misalignment here.

Paul Austin-Menear:
8 / 10 (Job Ad)
5 / 10 (Role Design)

Holy sh*t, there were no typos or written errors. They must have proofread. It’s sad that this makes them stand out… and the job ad itself was pretty good. But the structure of the role? Not so much. Why aren’t they allowing this candidate to interact with what will probably be the most fun part of the job (social media storytelling)? That makes no sense.

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Lead VIP Host: The Whale Who Loved Me

Paul Austin-Menear — Fri, 29 May 2026 07:21:53 GMT

Let’s Roast.

What does it take to keep the whales happy in a high-stakes, high-reward gaming world? This week’s job ad promises autonomy, equity, and a front-row seat to the VIP experience… but at what cost? Whether you’re a job-seeker wondering if you’ve got the charm to pull it off or a hiring manager looking to attract top-tier talent, this episode is your all-access pass to the good, the bad, and the downright risky of this Lead VIP Host role.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a role that balances the extractive nature of monetized gaming with the genuine need for human connection? This job ad forces us to confront the ethics of "whale wrangling" and asks: Can a company truly prioritize both profit and people, or is one always at the expense of the other?

At a Glance: The Job Profile

Job Title: Lead VIP Host
Report-to Title: Unknown
Company Size: 2-10 employees
Industry: Entertainment Providers
What do they do?: We are on a mission to redefine the skill games category, merging the best from casual play, into real-money adventures to entertain players for decades. AKA: monetized gaming platform with VIP revenue model.
Head Office Location: Jerusalem, Israel
Job Location: Global
Geographical Operating Area: Global
Job Type: Full-Time, 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:

Is this role right for me? Do I thrive in high-pressure, always-on environments where my success depends on building deep, personal relationships?
What’s the catch? How does the company define “unlimited vacation” in a role where the whales never sleep?
Am I okay with the ethics? Can I reconcile the extractive nature of this industry with my personal values?
What’s my exit strategy? If this role burns me out, what’s next for my career in gaming or hospitality?
How do I stand out? What unique blend of charisma, analytical skills, and industry experience do I bring to the table?

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.

Outcomes of Mistakes:

Unclear Structure: Without defining how this role fits into a 2–10-person team, you risk hiring someone who can’t scale with your growth—or worse, burns out trying to do it all.
Vague Perks: “Unlimited vacation” and “meaningful equity” sound great, but without concrete details, you may attract candidates who feel misled when reality doesn’t match the promise.
Ethical Blind Spots: Failing to address responsible gambling or the extractive nature of the role could lead to reputational damage or turnover from employees who feel morally conflicted.
Over-Reliance on Autonomy: While autonomy is a perk, without guardrails or support, your VIP Host may struggle to sustain performance—or their well-being.

Suggested Fixes:

Clarify the Org Chart: Even if you’re small, outline how this role interacts with other teams (e.g., analytics, leadership) and what “leading junior hosts” looks like in practice.
Define Perks with Numbers: Specify salary ranges, home office budgets, and how equity works (e.g., vesting schedules, dilution risks).
Address the Elephant in the Room: Acknowledge the ethical complexities of the role and how your company mitigates harm (e.g., responsible gambling tools, “whale” welfare policies).
Design for Sustainability: Build in backup systems (e.g., shared on-call rotations, temporary coverage) to prevent burnout in an always-on role.

The Verdict

Paul Austin-Menear:
7 / 10 (Job Ad)
6 / 10 (Role Design)

The job ad was well-written, easy to follow and understand. Pretty good marks there. They could have improved it with some employer branding and discussion of values. The job structure wasn’t well thought through though. It will hold back the company from growing to their true potential.

Jennifer Houle:
7.5 / 10 (Job Ad)
6.5 / 10 (Role Design)

I found the way that the job ad was written to be very compelling. There was something genuine about it, and I’m into it. So good job there…. but, the job won’t be very sustainable. It should have been structured very differently to bump the odds of success in the house’s favour.

Support the Show

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Golf Companion: Singapore Sling, Toronto Swing.

Paul Austin-Menear — Fri, 22 May 2026 07:17:37 GMT

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:

VIEW DOCUMENT

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.

SUPPORT THE SHOW

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.

Live Studio Audiences

Paul Austin-Menear — Wed, 20 May 2026 15:46:18 GMT

Regular episodes of Roast the Post are recorded in a virtual studio, generally on Friday afternoons. You can join us and watch the episode being recorded as we go—hilarious outtakes and all. During the show intermission, we chat with the audience and take questions =)

Getting your invitation to join our studio audience is free, and there are only a few simple steps:

Why do you need to follow both of us?

Like every good partnership, we share the work equitably. Jen and Paul alternate weeks hosting the show, and invitations to join the live studio session are sent from the host’s account.

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Product Designer: Worshipping at the Altar of Figma

Paul Austin-Menear — Fri, 15 May 2026 07:10:13 GMT

Let’s Roast.

Healthcare is broken. This company wants to fix it… by hiring a product designer to ‘stretch themselves’ under tight deadlines, absorb endless feedback, and ‘own’ a role with no clear responsibilities. Oh, and they’ll pay you $100K–$115K (if you’re lucky) and don’t mention benefits. Jen and Paul dig into a job ad that’s all mission, no clarity, and a masterclass in how not to attract top talent.

Is this the future of design work, or just another hustle culture bait-and-switch?

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a job for impact when the system is broken… and your own company is part of the problem?

This episode isn’t just about a flawed job ad; it’s about the tension between mission-driven work and exploitative expectations. If a company wants to “redefine healthcare,” it should start by redesigning its own hiring practices: clear responsibilities, fair compensation, and transparency about culture and support. Otherwise, it’s just another startup burning out designers in the name of “urgency.”

At a Glance: The Job Profile

Job Title: Product Designer
Report-to Title: Unknown
Company Size: 201 - 500 employees
Industry: Hospitals and Healthcare
What do they do?: Connect patients and families with dedicated healthcare advocates (like nurses and care specialists) who guide them through the healthcare system to improve outcomes and ensure they don’t fall through the cracks.
Head Office Location: Redwood City, California
Job Location: Remote, US
Geographical Operating Area: USA
Job Type: Full-Time

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:

What’s the real workload? Ask: “How many projects will I own simultaneously, and what’s the average timeline for feedback cycles?”
Who’s in the room? Clarify: “Who will I report to, and who else will be giving me feedback on my designs?”
What’s the growth path? Probe: “How does the company support professional development or promotions?”
Where’s the safety net? Demand: “What benefits (healthcare, retirement, etc.) are included, and how do they align with your mission?”

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:

Problem: Unrealistic expectations – Demanding “unrealistic timelines” and “pixel-perfect” work under ambiguity risks burnout and high turnover. Fix: Define clear priorities, realistic deadlines, and feedback loops. If speed is critical, explain why and how it aligns with long-term goals.
Problem: Lack of transparency – No benefits, reporting structure, or team details signal disorganization or a toxic culture. Fix: Include these basics in every job ad. Candidates (especially in mission-driven fields) need to trust you’ll support them as much as they support your mission.
Problem: Bias in hiring – Requiring video applications excludes introverts, neurodivergent candidates, and those without resources to produce polished content. Fix: Replace with structured written responses or asynchronous interviews. Focus on skills, not presentation.
Problem: Mission misalignment – A bold mission loses credibility if the company doesn’t “walk the walk” (e.g., no healthcare benefits for a healthcare company). Fix: Audit your employee experience. Does it reflect your external mission? If not, fix it before hiring.

The Verdict

Paul Austin-Menear:
5 / 10 (Job Ad)
Could Not Rate (Role Design)

I hated having to give the job ad this rating, because there was such alignment to purpose and so much was great about it. Too much was missing though, it was half finished. I couldn’t even rate the role design because there was so little about the role beyond fluffy hype words about making things beautiful.

Jennifer Houle:
5 / 10 (Job Ad)
Could Not Rate (Role Design)

The job ad is halfway there, with a LOT of missing pieces. They’re passionate about healthcare, but don’t even appear to offer health insurance to their employees. WTF? The role design was MIA. So, yeah.

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Director of Pedagogy: Peda... goo-goo? With Chief Absurdist Officer

Paul Austin-Menear — Fri, 08 May 2026 07:05:10 GMT

Let’s Roast.

What happens when a job ad asks for a "Director of Pedagogy" but really wants a jack-of-all-trades, master of none? This week, Jen, Paul, and special guest Chief Absurdist Officer (Kathi Eric Dalguntas) tear into a role that’s part teacher, part salesperson, part project manager… and 100% a hot mess. With a salary that’s more insult than offer and responsibilities that defy logic, this job ad is a cautionary tale for both job seekers and the companies that create them. Buckle up… this roast is heavy on charcoal crusting.

Follow along with the full job ad here :

VIEW DOCUMENT

The Bigger Picture

How do you design a role that balances expertise, scalability, and human limitations? This episode isn’t just about a bad job ad… it’s about the systemic failure to recognize that roles must be built for real people, not wish lists. When companies demand everything from one person, they set up both the employee and the organization for failure. The real question: How can we shift from “do more with less” to “design for success”?

At a Glance: The Job Profile

Job Title: Director of Pedagogy, e-Learning Instructional Design
Report-to Title: Unknown
Company Size: 51-200 employees
Industry: E-Learning Providers
What do they do?: Leverage advanced technology to provide personalized, industry-leading language learning ecosystems for K-12, higher education, and corporate environments.
Head Office Location: Toronto, ON
Job Location: Remote, Canada
Geographical Operating Area: Global
Job Type: Full-Time

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:

What’s the real priority here? Ask: “Which of these responsibilities is most critical to success in the first 90 days?”
Who’s on my team? Clarify: “Can you describe the team structure and who I’d be collaborating with most closely?”
Why is this role open? Probe: “Is this a new role, or am I replacing someone? If so, why did they leave?”
How is success measured? Demand: “What does success look like in this role, and how will it be evaluated?”
What’s the culture like? Investigate: “How does the company support work-life balance and professional development?”

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:

Role Overload: The job ad crams instructional design, sales support, project management, and cultural sensitivity into one role. Outcome: Burnout, high turnover, and poor performance. Fix: Split the role into 2-3 focused positions or clearly prioritize responsibilities.
Lack of Clarity: No reporting structure, vague expectations, and no cultural hooks. Outcome: Confusion, misalignment, and difficulty attracting top talent. Fix: Define the role’s purpose, reporting lines, and success metrics upfront.
Salary Insult: $70K–$80K CAD for a “Director” role with global responsibilities. Outcome: Low-quality applicants or rapid attrition. Fix: Benchmark salaries competitively and be transparent about compensation philosophy.
Cultural Red Flags: Glassdoor reviews cite toxicity and lack of vision. Outcome: Reputation damage and difficulty retaining talent. Fix: Address cultural issues publicly and align job ads with real employer branding.

The Verdict

Chief Absurdist Officer:
3 / 10 (Job Ad)
4 / 10 (Role Design)

It’s hollow, and it’s a Frankenstein job. The ad was poorly written, and the role design suffered from a lack of thought and foresight. Booooooo.

Paul Austin-Menear:
3 / 10 (Job Ad)
2 / 10 (Role Design)

Brutal job description, brutal role design. The only candidate who could actually do this job as described, without melting into a puddle on day one, is Sam Altman’s Claude-enabled Chia Pet. He wouldn’t even want ChatGPT to touch this one.

Jennifer Houle:
1 / 10 (Job Ad)
1 / 10 (Role Design)

This one hurt my brain. It makes me want to redesign our scoring system so that I can give them a participation ribbon instead of a score. There’s nothing of merit in this.

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Roast the Post LIVE: Happy Hour

Paul Austin-Menear — Tue, 05 May 2026 16:07:00 GMT

Let’s Roast.

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 last week though—the stars aligned, and they were in the same city. Catch the replay on your favourite podcast app or watch on YouTube or Substack.

The Bigger Picture

Audience Questions Covered

Kathi: In a better world, what would the jobseeker’s experience look like if you could have it your way?
Sam: When an HR employee asks about your salary expectations during a job interview, is it a good idea to say how much you currently make? What if they offer you lower than your current wage? General negotiation tips?
Max: What to do if you get lowballed?
Max: How do interviewers measure “cultural fit”?
Max: Should I say the true reason I’m leaving my current job (toxic)?
Max: What if I mess up during an interview?
Mike: Thoughts on digital nomads and remote work?
Sam: Length of typical hiring process?
Sam: Thoughts on letting employees push out their start date or do they need to start immediately?

Did Jen and Paul cover all of the questions submitted by the audience live or in advance? Not even close. Stay tuned for a special session where they tackle the rest from the studio.

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VP, Enterprise Sales: The Scorpion and the Frog at the River

Paul Austin-Menear — Fri, 01 May 2026 07:11:46 GMT

Let’s Roast.

What does it say about an organization when its VP of Sales role reads like a Wall Street boiler room job… but for nonprofits? This week, Jen and Paul dissect a job ad that demands $25M in new revenue, a 40-person team, and a compensation package so opaque it might as well be written in invisible ink. But the real womp-womp? The company’s mission is to make giving easier for charities. So why does this role feel like it’s designed to burn out its leader, and what does that mean for the causes they claim to serve? Buckle up: this roast is equal parts eye-opening and infuriating.

Follow along with the full job ad here:

VIEW DOCUMENT

The Bigger Picture

How do you design a high-stakes sales role for an organization whose mission is philanthropy, without turning it into a zero-sum game? This job ad exposes the tension between revenue growth and ethical responsibility, forcing us to ask:

Can capitalism and charity coexist in a single role? And if so, which thumb is on the scale?

At a Glance: The Job Profile

Job Title: Vice President, Enterprise Sales
Report-to Title: Unknown
Company Size: 201-500
Industry: Software Development — Fundraising Software
What do they do?: Donation platform helping nonprofits engage more supporters and grow revenue by providing easy ways to increase conversion, enable modern payment methods, and personalize the giving experience for every donor.
Head Office Location: Brooklyn, New York
Job Location: Remote (USA)
Geographical Operating Area: Global
Job Type: Full-Time / Permanent

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:

What’s the real base salary? The ad only lists “on-target earnings”. How much of that is guaranteed, and how much is variable based on performance?
Who do you actually report to? No reporting structure is listed… how will you navigate authority and decision-making?
How will you manage 40+ direct reports? The ad mentions coaching and retention, but is that even possible without burning out?
What are the ethical guardrails? With revenue incentives this aggressive, how do you ensure alignment with the nonprofit’s mission?
What’s the turnover rate for sales positions on the team? If retention is a listed responsibility, what’s the history here? What are some of the historical challenges?

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:

Lack of Transparency: Bundling compensation as “on-target earnings” without clarifying base salary is deceptive and could deter top talent.
Unrealistic Span of Control: Managing 40+ direct reports is unsustainable, expect high turnover or poor performance.
Ethical Misalignment: Aggressive revenue targets in a nonprofit context risk reputational damage and mission drift.
Authority Ambiguity: No clarity on reporting structure or decision-making power leaves the role powerless to enact change.

Fixes:

Restructure the Team: Break the 40+ reports into smaller units with clear leadership layers.
Clarify Compensation: List base salary, bonus structure, and equity (if applicable) upfront.
Define Ethical Guardrails: Explicitly outline how revenue goals align with the nonprofit’s mission.
Add Outcomes to the Job Ad: Specify what success looks like in 3, 6, and 12 months… not just revenue targets.

The Verdict

Jennifer Houle:
7.5 / 10 (Job Ad)
5 / 10 (Role Design)

The job ad was fairly well-written, though missing some important nuance for a VP-level role in a serious organization. The role design… worried me. This person is going to be constantly battling competing management priorities all while being compensated mostly based on revenue targets.

Paul Austin-Menear:
4 / 10 (Job Ad)
5 / 10 (Role Design)

It all sucked. The ethical conflict in the incentive structures were brutal. The job ad was missing honesty around earnings, and squished together a bunch of incompatible expectations. The role design… well, you might be able take your first week of vacation in around the year 2061. Like, come on.

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