- Support Human
- Posts
- 30Mar25 Bad Job Bingo
30Mar25 Bad Job Bingo
On free speech and economic engines.

In this issue:
On free speech and economic engines
We’re doing things a little bit differently today. We’ll still have a few regular BJB jobs under their original ratings, but first…we’re going to talk about one job.
That job? Substack’s Head of Standards & Enforcement (formerly Trust & Safety).
If ever there was an example of a company and job that Bad Job Bingo — as a practice — was created for, it's this one.
No job is ever worked in a vacuum. Still, this one struck me as especially emblematic of the problem that Bad Job Bingo was created to address: All the choices Substack has made as a company inform what this role will actually be like, and that's impossible to fully appreciate without looking at the company holistically.
I mean, y'all. They changed the name of this position's department from Trust & Safety — talk about industry standard! — to Standards & Enforcement. Aside from the bitter, fascist flavor of that name, what does it tell us?
It tells us that Substack's priorities aren't for creators and users to trust the platform is promoting accurate information or even the bare minimum of ensuring their safety. Substack has one mission and one mission only, which they are at least being honest about: protecting their economic engine and enforcing the rules that make it run.
But I’m getting ahead of myself. If you’re a longtime follower of Bad Job Bingo, you know that I start with a company’s Carreer’s page, because it’s a company putting its best foot forward (unfortunately, that foot is often dirty and crusty and in need of a pedicure, but that’s a rant for another time).
Substack’s career page, like many Tech companies, is mostly fluff with some useful information thrown in. It also has a pretty standard Values section, which ends with this:
We believe in the free press and in free speech. We do not believe these things can be decoupled. You can read more about our views on content moderation on our blog.
Now, you could do that. Or you could simply read this quote from the very first issue of this newsletter:
When confronted with widespread criticism of Substack’s Terms of Service and moderation policies, company Co-Founder Hamish McKenzie said, among other things, that:
[A]ggressive content moderation” didn’t work. “Is there less concern about misinformation? Has polarization decreased? Has fake news gone away? Is there less bigotry? It doesn’t seem so to us.
Because why even try to responsibly moderate your platform when racist antisemites have so much disposable income, amiright?
Yes, one of the very first topics I covered in the Support Human newsletter was the fallout from Substack not only failing to moderate Nazis and white supremacists, but actively courting them. Unsurprisingly, this problem has not gone away.
But why would it, when Substack wants to confuse exploiting bigotry for incredible profit with taking a stand on free speech? For instance, this is how Substack introduces the Head of Standards & Enforcement role in the job description:
Substack’s mission is to build a new economic engine for culture. From the beginning, we have been clear in our belief in the free press and free speech—values we consider inseparable and fundamental to a trustworthy media system.
This statement is frankly diabolical on its own, but think about what it really means: "We want to devise new and creative ways to squeeze every drop of profit from the bonds that build community among you."
Add "we believe in free speech" to that, and you have a company that cares so much about monetizing our communities that they don't care if they pervert or destroy those bonds in the process.
Don't take it from me, though. Take it from them. They say it pretty plainly (bolding mine):
This is not a traditional Trust & Safety role. We are looking for someone eager to rethink how platforms handle policies and enforcement—eschewing centralized censorship in favor of empowering creators to set the tone for their communities. You will lead a team, oversee enforcement, develop policies, and partner with Product to guide the platform’s evolution.
This role is about protecting Substack’s viability by addressing extreme behaviors while respecting the fundamental freedom of users to express their perspectives.
In other words, this role will somehow have to find a way to protect Substack’s economic engine while simultaneously making sure Nazis get to say what they want.
Next, we get some interesting insight into how this department is structured:
This position reports to the VP of Operations.
This is a company whose entire business model relies on content creation, it’s a company that is still a behemoth in its space, and yet apparently the most senior Trust & Safety professional in the organization is only a Head Of?
Is it possible that they don't actually want to empower their Trust & Safety — sorry, Standards & Enforcement — teams to do any kind of content moderation above what’s legally required to stay in business and know that an executive worth anything at all would challenge that?
Hmm. A real mystery there.
The Responsibilities section includes fairly run-of-the-mill duties, although this bullet drives home to me how much more they care about “rule enforcement” than devoting real human effort to making their platform safe and trustworthy:
Drive forward Automation and AI. Get your team partnering with engineers and vendors. Leverage emerging tech to gain superpowers that enhance detection, automation, and decision-making to make rule enforcement faster and more effective.
The Qualifications section similarly has some points that make me pause. This one, for instance:
Problem-solver with a startup mindset. Hands-on and proactive, you excel at navigating complex challenges in a fast-paced environment.
Startups look for a certain mentality because they usually don’t have the time or the resources for heavy processes or lengthy deliberations in decision-making. Of course, as companies grow, so does the complexity of their operations and their risk, but their capacity to manage those operations and risk should grow as well.
And anyone working in Trust & Safety has to be comfortable assessing complex situations and making quick decisions based on those assessments; I’m not contesting that.
My issue is the larger pattern here: Substack is not a startup at this point, and it’s concerning that 1) they seem stuck in a stage of maturity they should have grown out of some time ago, and 2) they seem so averse to giving content moderation the consideration and resources it deserves despite having the time and resources to do so.
5+ years experience in Trust & Safety, content moderation, risk, threat disruption, or a related field, ideally in a lead role. Candidates with a product background who have worked on Trust & Safety features are also encouraged to apply. Seeking candidates with experience working on social media, social networks, and other content-focused platforms.
We’ve sort of addressed this already, but Substack is a major content platform. Not only is the title for this role not senior enough, but I also don’t think the experience they’re targeting here will adequately set up the person in the role for success (which, you know, could be the point).
Also, Trust & Safety is not a product, it’s a practice. Yikes.
Substack’s compensation package includes a market competitive salary, equity for all full time roles, and exceptional benefits. Our cash compensation salary range for this role is $145,000 - $195,000.
This would be laughable for any Head Of role at a company like this, but given they want this persion to be onsite in San Francisco, it’s really fucking laughable.
Look, I’m not telling you to not apply for this job if it interests you. In fact, I’m not rating it at all because that’s honestly unnecessary at this point.
What I do want you to do is this: Before you apply, I want you to think very carefully about what it would mean to try to lead the content moderation function at a company that doesn’t believe in content moderation.
I want you to imagine logging in every day and having to figure out, in your capacity as the Head of Standards & Enforcement, what kind of content violates your company’s standards when one of your co-founders is doing things like personally recommending the publication of a dude who called the Holocaust humane (which is currently the #1 history newsletter on Substack).
The results of that exercise are no one’s business but yours. We all have economic engines we have to fuel. Just make sure you’re really okay with fueling Substack’s.
There are so many great ways to support this newsletter! You can upgrade to a paid subscription or give a one-time donation or you can share this newsletter with a friend.
Another great way to support is to check out this week’s sponsor, Morning Brew! Like Support Human, Morning Brew offers a free newsletter, with the added bonus of providing your daily dose of news and humor.
Come for the news, stay for the laughs
Morning Brew isn’t just any newsletter—it’s your free shortcut to business news that actually matters. Fast, fun, and—dare we say—enjoyable.
No fluff, no jargon, and it takes less time to read than it does to brew your coffee (unless you’ve got a Keurig—then you might get to enjoy your Morning Brew with your actual brew).
Join over 4 million professionals who read it daily. Delivered bright and early, it’s news on your time—whether you read it when you wake up, over lunch, or before bed.
Get Hired
I play Bad Job Bingo with every job listing that appears in the Roundup and categorize them according to how well (or poorly, if I hit Bingo) they do in the game.
However, please remember that a job appearing in a positive category isn’t an endorsement of any role or company, and a job appearing in a negative category doesn't mean I think you shouldn't apply if it works for you. Bad Job Bingo is simply an effort to give you a shortcut to finding roles that may match your needs and values.
These and past contestants can be found at Support Human Jobs.
Green Means Go
No flags, or green flags only! A true unicorn.
Sadly, none this week.
Eh, It’s Probably Fine
A few flags popped up, but no serious ones.
Director of Customer Education ($170k-$190k) at SimplePractice (Remote US-Los Angeles, CA)
Maybe I'm just a cynical bitch (maybe, LOL), but their values are pretty woo-wooey, and considering some of the other jobs we've seen from "health and wellness" companies, I'm a little anxious about this one.
The Benefits section only lists actual benefits and the benefits themselves are decent, but that's pretty much it for actual info about the company on the Careers page. It's a little underwhelming.
We are seeking a strategic and results-driven Director of Customer Education to lead the development and execution of scalable education programs for our customers. — Job descriptions obviously have tropes just like any other genre of writing, but I feel like I've read this exact sentence so many times recently that I'm no longer playing Bad Job Bingo but a really boring game of Mad Libs.
Reporting to the Chief Customer Officer — Well hey, I love this. It's so rare to see this position in any company (Tech or otherwise), I see it as a green flag.
the ideal candidate will collaborate closely with Customer Marketing, Product Management, and Customer Success to enhance customer engagement and satisfaction. — Ideal candidate statements should detail what qualities and experience the candidate needs to have to be successful, not just a simple statement of what they'll do. AI has ruined job listings, ask me how.
Collaboration with Customer Marketing: Work closely with the Customer Marketing team to ensure education initiatives align with broader customer engagement and retention efforts.
Collaboration with Product Management: Partner with Product Management to ensure that customer education materials reflect the latest product updates and enhancements — This is also great. This kind of collaboration should be a given, but it so often isn't, so it's nice to see it spelled out.
$170,000 - $190,000 annually — This salary is excellent and actually competitive. See what can happen when you have a CCO?
I'm glad that my anxiety was proven unnecessary – this sounds like a great job with great pay and benefits. They do ask for salary expectations, but it's not a required question, so not sure what to make of that.
It's not so outstanding that I feel comfortable giving it a Green Means Go, but it's a high Eh, It's Probably Fine.
Customer Success Manager ($170k-$190k) at Procurify (Remote CAN-Vancouver, BC)
Procurify has a well-developed and informative Careers page, including what to expect during the interview process.
Comfortable working independently as well as part of a team in a fast-paced environment — Damn, they almost escaped this trap! Alas.
Unlimited responsible time off: Work hard, play harder. All team members can take advantage of our unlimited responsible time off policy. — Struggling on the dismount here. Also, you can't introduce a term like "unlimited responsible time off" and then not explain what it means. What kind of time off counts as responsible? And if time off has to be "responsible," is it really unlimited?
The salary is $73,000-$90,000 CAD, which is roughly $51,027-$62,910. This would be pretty terrible for a CSM in the U.S., but I'm not qualified to say whether this is a good comp in Canada. If you live and work in Canada, please chime in!
Overall, this is a solid Eh, It's Probably Fine. Aside from a few flags (and asking for salary expectations on the application), it seems like a decent remote role with good benefits.
Tread Carefully
Didn’t quite hit bingo, but there were several yellow flags or more than one red flag.
Customer Experience Associate ("Competitive" comp not given) at Melio (Remote US-Denver, CO)
Melio's Career page is one in name only; no information about the company, just a list of open roles.
We need dynamic go-getters, eager to conquer the unique challenges of a startup environment, ensuring every customer feels valued and supported. — I'll take "Which job description was written by AI?" for $800, Alex.
Here, your role transcends typical customer experience duties; as a pivotal part of our team, you'll be actively involved in brand-building, retention and turning every customer interaction into a moment that defines and enhances the Melio brand. — Mmmhmm. The salary better transcend the typical customer experience salary, then.
Comfortable in a fast-paced startup environment, while being able to stay patient while managing a variety of situations — Better come with startup pay.
We don’t just solve issues, we consider ourselves Brand Builders and this differentiates us from the competition. — The pay better differentiate you from the competition, etc., etc.
Competitive compensation packages: We strive to make each and every employee feel valued and appreciated. The annual base salary range for this position is $45,000 - $55,000 — *stares at camera*
Yeah, no. Tread Carefully.
BINGO
Welp.
Technical Support Analyst ("Competitive" comp not given) at Tabs (Remote US-NYC, NY)
We’re looking for a highly capable, fast-thinking Technical Support Analyst to help manage the increasing volume of technical support requests from our merchants (a Tabs customer). — Why do you have to start off with ableism? Is it really necessary for this person to be "fast-thinking"? What does that even mean?
If you thrive in high-stakes, fast-paced environments, love solving problems and are obsessed with providing merchants with a world-class experience, we want to hear from you! — "High stakes" in a job like this means the product doesn't work, or only works enough to be dangerous. You're there as a human shield between the customer and the product, and I promise that isn't even as fun as it sounds.
This role is perfect for someone with a sense of customer empathy — A single sense of empathy. Just one.
comfortable in ambiguity, and a desire to help merchants solve complex problems. — You'll get zero support and will be expected to make the product work anyway. SO FUN.
Resolve complex support issues from merchants via email, Slack, and chat, ensuring fast, clear, and accurate responses. — Oh god, chat as a channel for solving complex financial issues sounds like a nightmare.
I will, however, give them points for offering examples work that will be done in the role. That's rare to see and a helpful way for candidates to determine whether they're really interested in the job.
Exceptional problem-solving skills—you’re resourceful, detail-oriented, and able to think on your feet. — They keep saying this and I think the major problem is that they're not being specific enough. If you can give examples of work, then it stands to reason you can be clear about the kinds of problems candidates will face. For instance, they could said that candidates need experience with data reconciliation, accounting practices, invoicing, etc. "Problem-solving" is so nebulous as to be useless.
Ability to manage high ticket volume while maintaining high-quality responses. — This is a red flag. In a financial product like this, you can have a fast response rate or you can have high-quality responses. Unless you are very robustly staffed, you can't have both.
Ability to thrive under pressure, quickly assess problems, and deliver solutions in real-time. Experience working in a fast-paced startup or technical environment preferred. — The number of times they've repeated this is its own red flag.
Still no salary, still a BINGO.
Customer Success Manager ("Competitive" comp not given) at Tabs (Remote US-NYC, NY)
Innovate In-Person: Collaboration requires an open and safe forum for the best ideas to emerge — This is a weird and confusing value - what does being in person have to do with collaboration? I'm not saying there's no possible connection, just that if your value calls out working in-person specifically, you should explain why.
Build the best vision: Ideate and debate where the world can go, then urgently execute to realize that future — Y'all. What.
Growth from Discomfort: Progress comes when we step out of our comfort zone — I dunno, this being a value in context with these others feels like a red flag.
Complimentary meals Free lunch and dinner in the office — DINNER in the office? No thank you please.
Regular team events - We work hard and play hard — NOT A BENEFIT and also I HAVE CONCERNS
If you're interested in the intersection of industry-leading AI with B2B finance and automation technology, let's talk. — Oh yeah, okay. That checks out.
Deploy customer success strategies to ensure an outstanding customer experience with Tabs, driving customer satisfaction and retention. — I'll take "Which job description was written by AI?" for $1000, Alex.
Actively engage with clients to anticipate their needs and provide solutions that enhance their experience, while also being responsive to support tickets and inquiries via Slack to address immediate issues. — I think the AI is confused about what Customer Success does.
Set the strategy and monitor success: Help define clear objectives and key results for the customer success function, adjusting strategies in response to evolving business needs and customer feedback. — This is not an IC duty, and they are not at all clear if this is a regular CSM role (with that standard title) or if it's an honest-to-god manager role. I think the AI IS just real confused.
A proactive self-starter who thrives in ambiguous environments and is skilled at building functions from the ground up. — So many flags, so little time.
Eager to learn, adapt, and scale within a fast-paced, evolving startup atmosphere. — "Hey ChatGPT, give me alternatives to saying 'dynamic environment.'"
"Competitive compensation and equity" with no salary based in Manhattan. LOL K.
Seriously, Maybe Don’t
Don't say I didn't warn you.
Thankfully, none this week.
Reply