16Mar26 Bad Job Bingo

Twilio has devoted a lot of resources to its Careers page and it shows. Twilio's mission is lofty yet focused and grounded, and its values are well-conceived. Their senior leadership team is gender-balanced, and their CFO and CPO are both female-presenting. So far so good!

See yourself at Twilio — I always appreciate it when companies phrase their pitches to candidates in inviting ways, rather than with negative, aggressive language like "see if you have what it takes!" It's a small thing that ends up being a big indicator of company culture.

The Sr. Manager will lead the Personalized Support teams composed of Managers of Technical Account Managers and Tech Leads. You will be a key member of the Personalized Support leadership team and will build bridges with the other functional teams across Twilio. — Love that they specify that you'll be managing managers and leads. I do wish they were clear about how many people you'd be overseeing, as that's an important number for leadership effectiveness and sustainability, but you can ask about it when interviewing.

Create a culture that attracts and retains outstanding talent and partners with functional leadership to meet/exceed all operational targets. — Also a good sign that they specifically call out retaining talent.

Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table! — I have to say, this is a great job to kick off this BJB batch. I'm really enjoying all these green flags.

Able to work in a dynamic, ever changing environment with a strong bias toward action. — You were doing so well, Twilio! Given that your team clearly knows how to craft a job listing, I would expect you to be able to define what this means in the context of this team. I know you can do better than this!

I think the above flag is a minor one in the greater context of the role, and the pay is excellent, so I'm pretty comfortable putting this in Green Means Go.

Note: Twilio explicitly states that this role can't be hired in CA, CT, NJ, NY, PA, or WA. Twilio is also hiring for several other Support and adjacent roles around the world, so worth taking a look at their Jobs page.

Brace yourself for an in-depth analysis of Ashby's Careers and Culture materials; I wouldn't normally do this, but considering it's hiring software, it feels appropriate.

There's an odd, rant-like bit on Ashby's careers page about how software products are built. It's not that I disagree with it; it's more that it feels off-topic for a Careers page and thus makes the Careers page seem amateurish and haphazard, which is not a great sign considering Ashby is largely hiring software. It's just weird for a company that should know what it's doing with a Careers page.

Ashby's Culture page is very informative, but it's laid out like a blog, so the posts include dates. This is mostly fine, but it does give the impression that the Culture page hasn't been updated in a while. Again, this is just a polish thing, but given that Ashby is hiring software, it comes across as odd.

Another polish thing that makes me pause: There's a note at the top of Ashby's Operating Principles stating that they consider it to be a "v1 document." But this was published in February 2023, so why is a 3-year-old document still on version 1?

You should always review any materials a company gives you, and it's always a green flag when companies include extra material about their culture, how they operate, etc. I think you should make up your own mind about Ashby's Operating Principles, but FWIW, I think these are really just Values in different clothing, and I find their explanations of the principles muddled in places. It also feels like Ashby positions its culture and principles in opposition to what other software companies are doing, rather than letting its practices stand on their own merits. To me, this is a minor flag I'd keep an eye on during interviews.

Also, a lot of Ashby's materials are written by its CEO and co-founder, so he's obviously pretty opinionated. This is not necessarily a bad thing! It could mean that he has a good bead on what he wants his company to be, or that the leadership culture is prone to micromanaging. It could mean both. This is where asking specific questions about culture and taking note of who you have access to during the interview process is paramount.

Looking at Ashby's leadership team, it unfortunately hits these BJB squares: All the women on the leadership team are from Support, Marketing, or Admin, and all the women on the leadership team are white. Aside from that, though, the company seems to be very diverse across teams, so that's a plus.

Finally, here's a big green flag: Ashby lists pay for all positions on the Jobs page (so you don't have to click into the listing to see it), and it does this even for non-US roles. That is a HUGE plus in Ashby's favor, in my opinion.

Okay, on to the job description!

Hi I’m Kelsey 👋 – VP of CS at Ashby. One of my favorite Ashby principles is Implementing Continuous Improvement; it guides how we continually raise the bar on the customer experience. I’m thrilled to be hiring a Head of Global Support to lead our global team and take our world-class support to the next level. — I love that they include this note right at the top of the page.

The "About this role" section is exceptional -- it includes details on the structure of the team this role will lead, how many direct reports they'll have, and a solid overview of what the role will need to accomplish. It's also very complimentary of the existing team. Love it.

The role requirements are thorough and well-articulated. The "You could be a great fit if" section is mostly good, although I'm not the biggest fan of this bullet, because I don't think it's defined properly:

The "This role may not be a great fit if" section is also excellent and clearly written by someone who understands support well and knows what they're looking for in a candidate.

I love that the interview process is clearly laid out, though it makes me curious about the broader structure of the Support function at Ashby: they mention a VP of CS, a Head of Support, and a Head of CS. Again, this isn't a negative; this is just professional curiosity on my part about how they delineate these roles from each other.

The Benefits section is oddly organized, placing "You’ll get the time to do things the right way" at the top of the list and health insurance info at the very bottom, which, again, I just think is a weird polish thing to miss if you're hiring software.

All in all, I think the role itself seems great and is expertly targeted to the candidates they're looking for. However, if I were applying for this role, I'd have questions about broader company culture, so I think Eh, It's Probably Fine is the best fit.

Note: There's a deadline to apply to this role of March 23, 2026 at 12:00 PM ET. Also, Ashby is hiring for many Support and Success positions worldwide, so be sure to check out their Jobs page!

Scribd's Careers page is just okay. It has some info, but I'm not overwhelmed with knowledge about their culture or operations, which is ironic considering they're a self-proclaimed knowledge company.

There's also this bit:

This posting reflects an approved, open position within the organization. — Okay, well now I think it's a ghost job, because why else would you feel the need to say this? Maybe I'm just too suspicious. That's also always an option.

We're looking for a leader who views AI not just as a tool for efficiency, but as a fundamental shift in how we engage with our community - someone who will lead the transition from traditional support to an AI-first operation that scales our reach while deepening human connection with our audiences. — I mean, at least they're upfront about this? But uh...good luck with that.

Serve as a strategic partner to executive leadership, shaping reviews, operating rhythms, and performance reporting. — Do they mean for the Customer Ops function, or the company as a whole? Again, not sure why they aren't getting specific with these requirements.

Advocate for C-Ops across the organization, securing resources, tooling, and organizational support. — Oooooooooof. Good luck with that.

Own the Customer Operations technology ecosystem, including Zendesk, Forethought, Help Center, and future tooling investments. — Ahhh, okay, at least that gives some insight into the AI-first thing.

Lead the evolution from traditional support infrastructure to an AI-augmented operation that scales our capacity while deepening customer relationships. — LOL, there it is again. I'd be asking some serious questions about exactly what they mean by this, because it sounds more like unrealistic expectations to me. What is being AI-first enabling the Customer Ops team to do? Is there a community program, or do they want one? What are the avenues for deepening customer relationships if customers are talking to AI for most of their interactions with Support?

Have they thought this through, or is this just something the AI put into this JD and they liked the sound of it?

Champion a "support-first" approach to product development. Partner with Product and Engineering to embed self-service capabilities and intuitive design into our products from the ground up, reducing friction before customers need to reach out. — Again, shit like this is almost always a red flag. It's transparency for sure, just not in the way companies think it is: Scribd is being transparent about not being a customer-first organization in which every team contributes to customer happiness. It's saying the rest of the company doesn't want to deal with customers, and you're constantly going to be nagging them for the smallest scraps to improve the customer experience.

Build measurement frameworks that go beyond traditional support metrics (CSAT, FRT) to track what matters: AI deflection effectiveness, cost-per-resolution, impact on customer lifetime value, and leading indicators of churn risk. — Woof. At least we know what they think really matters!

Benefits at Scribd, Inc.: Scribd Flex (flexible work model) — Okay, first (and you know this song!), this is not a benefit! and second, WHAT DOES THIS MEAN

Enterprise access to leading AI tools — Debating whether this should be a new Bingo entry, because what are they expecting here? Any experienced professional knows better than to use work resources for personal projects. So why would this be a benefit?

Honestly, despite my misgivings, the right person going in with their eyes open would probably kill in this role, as long as Scribd was honest about the challenges. I think this is a pretty solid Tread Carefully.

See Wiz's Director, Critical Accounts Support role for my opinion on its empty wiz-bang approach to a company pitch.

You’ll collaborate across product, customer success, field and marketing to make sure the community isn’t just active, it’s valuable. You’ll also help show how community engagement drives satisfaction, adoption, and long term growth. — In another company's hands, I'd find the fact they called this out good, or at least fine. In Wiz's hands, that this is an argument that still needs to be had despite an already existing community makes me hella nervous. It sounds like this community manager would constantly be fighting a battle across the company that leadership should have already won.

Proven ability to work in a fast-paced environment and come up with creative solutions to challenging problems. — In the context of what should be a fairly chill tech community role, this is a red flag, especially undefined as it is.

Having said that, the other role duties and requirements seem fine, and the pay is actually pretty good for a community role (which are often undercompensated for the important role they play).

I'm going to say Tread Carefully for this one, balancing a mostly normal JD with my concerns about company culture.

Wiz's Careers page is pretty basic and lists snacks, meals, and company swag as benefits. Alas.

As the fastest-growing startup ever — I can't find any real evidence for this claim, other than Wiz just says so.

Our Wizards from over 20 countries work together to protect the infrastructure of our hundreds of customers, including over 50% of the Fortune 100, who trust us to scan and secure over 230 billion files daily. We’re the leading player in a massive and growing market, but it’s still early enough for you to make a significant impact. [...] Come join our team and help us create secure cloud environments that allow the best companies to move faster. — That Wiz is starting a job description with so much bluff and bluster and so little substance really annoys me.

Your primary goal is to stabilize these critical relationships by solving immediate technical debt and streamlining how these customers interact with Wiz. […] Own the resolution of critical issues by establishing strong relationships with internal technical teams, including the CTO, Engineering, and Product departments, and driving the path to success. — Either something is in the water all of these companies are drinking, or they're all using AI to write these JDs. Are they just not reading what's been written at all? For fuck's sake.

Unless this role also has authority over the CTO, Engineering, and Product, how exactly are they supposed to own the resolution of critical issues? They'll just be responsible for outcomes, while having no authority over the teams actually doing the work. It's just setting whoever's in this role up for failure.

Either this is intentional, which means this role is a scapegoat for every organizational problem, or it's not, which means Wiz has no idea what this role should really be doing and let AI decide for them. Neither is excusable.

I sentence this role to BINGO, with prejudice.

Hmm, I have a feeling that going from the Twilio job to this one will be a big leap. Or maybe more like a sharp drop.

There is no real Careers page, and the About page is about as bare-bones as it gets. What info we do get about the company is not flattering; for example, Riot Platform's leadership team is entirely male. Welp.

At Riot, we’re building the future of digital infrastructure. Our team members have unparalleled opportunities to work on groundbreaking initiatives. Through technical excellence and strategic execution, Riot has positioned itself as a leader in the industry driving advancements that continue to set new benchmarks in digital infrastructure. We are trailblazers. Problem solvers. People who thrive in fast-paced environments, communicate clearly, and bring relentless focus to efficiency and execution. — They put this under "What We're Looking For," but it doesn't actually answer that question. Also, way to put the least amount of effort into pitching your company to candidates!

The "About the Role" section includes things that should be in the "What You'll Do" section, which only adds to the impression that this was put together very haphazardly. I'm fully expecting an Attention to Detail requirement.

Execution oversight: Track deliverables, milestones, and service commitments. Hold internal teams accountable for meeting commitments. Maintain compliance dashboards and audit-ready documentation. — Is this role also going to be overseeing those internal teams? Because otherwise I'm not sure how it can be expected to hold those teams accountable.

Cross-functional collaboration: Partner with Operations, Legal, Customer Success, and Engineering to resolve compliance challenges and maintain accountability. — Yeah, good luck with that.

Proved track record of building and sustaining customer relationships. — Attention to detail is coming any minute now.

Ability to read, interpret, and explain complex contracts and technical SLAs. — ABILITY TO READ???? I'm dying.

Excellent organizational skills, attention to detail, and ability to manage multiple priorities. — WHAT DID I TELL YOU

Proven ability to drive accountability and maintain professional relationships under pressure. — This deserves a WOOF and a YIKES.

The fact that the pay is genuinely competitive is the only thing saving this job from Seriously, Maybe Don't. BINGO it is!

Note: I can't seem to link directly to the application, and the formatting for this JD was extremely irritating to deal with. This doesn't really have any impact on the job itself; I just needed to complain about it.

DispatchHealth seems like a neat company, but its website is pretty wonky, which doesn't inspire confidence. Their Careers page is very basic and without any real info as to culture, benefits, etc., and the apply button directs candidates to a totally separate tool to apply (similar in function to Workday, my condolences).

Lead response efforts for P0/P1 incidents with calm judgment and structured execution. Conduct post-incident reviews, including root cause analysis and blameless postmortems, and drive corrective actions — I don't know what it is with healthcare companies trying to offload key Engineering tasks onto Support functions today, but again, this is not a Support responsibility.

Root causes and product quality indicators. Ensure transparency and alignment across leadership, Product, and Engineering teams. Cross-Functional Collaboration & Product Quality. Partner closely with Product, Engineering, Clinical Operations, and Customer Success teams. Proactively identify systemic issues and product quality gaps. Translate support insights into actionable product and operational improvements. Advocate for customer needs while balancing engineering and operational constraints — 1) Not only are almost none of these the responsibility of Support, but 2) are they trying to win a contest for how many ways you can say the same thing? If so, they're winning.

The job description has some obvious typos and omits standard info, like the role's location and benefits. Overall, I don't think the company presents itself well, and I have concerns about what this role is expected to do. I don't think we've quite hit Seriously, Maybe Don't, but it's definitely a BINGO.

Medical and dental companies have historically fared poorly in Bad Job Bingo, so I'm very interested to see how this one turns out.

We are the Global Leader in dental management, analytics, communication, and marketing software — Is there, like, an official title of "Global Leader" that this company has somehow earned? If not, why are they randomly capitalizing that?

When TECHNOLOGY connects, more data is shared, more tasks are automated, and more work gets done. And most importantly, dental professionals have more time to focus on providing a quality experience for their patients. — Why are you yelling at me about technology?

All of this came from a small section on the Careers page, which is to say there is no real Careers page to speak of.

The fact that this role is titled Customer Loyalty Advocate but is handling "customers seeking to reduce, terminate, or change their HSOne account products or subscriptions" already feels like a red flag. Is this one of those SiriusXM situations in which you have to go through all nine circles of Hell in order to cancel your subscription?

Attention to detail and the ability to do active listening with customers and deliver clear and concise internal feedback will be key. — I'm glad we're setting expectations about this job listing early.

Encourage clients to utilize our best practices, ensuring they maximize the value of our products and services with existing resources they can derive value from — I hope both this role and Henry Schein One's customers have fireproof clothing.

Proactively engage clients that are delinquent on payments — Much attention. So detail.

Must have: Typically, 2 to 3 or more years of increasing responsibility in terms of any applicable professional experience. Typically, a bachelor’s degree or global equivalent in related discipline — Typically or actually? Also, how much do you want to bet that the pay for this role does not reflect that bachelor's degree or equivalent experience requirement?

Excellent interpersonal and conflict resolution skills and ability to deliver difficult messages — I mean, of course. They need to be able to navigate the inferno.

The posted range for this position is $60,000.00 - $64,000.00 which is the expected starting base salary range for an employee who is new to the role to fully proficient in the role. — We win! I think Henry Schein One owes us $1,000,000 dollars for subjecting us to this nonsense.

A great place to work with fantastic people. — Damn it, now you've done it. To Glassdoor, away!

So, yeah...I think we've got a BINGO on our hands.

See this company's Customer Loyalty Advocate role for another BINGO. My hopes are not high for this one either.

The "What you will do" section is a formatting mess. Also, this job description desperately needs proofreading; this bullet being a great example:

Balance customer satisfaction with operational stability and long-term platform health. — Woooooof. 1) This is the responsibility of company leadership, not Support, and 2) fix your product, my dudes.

Identify and mitigate risks related to recurring issues, technical debt, and system scalability. — This is not Support's responsibility! Furthermore, while we can certainly identify risks, we have no levers to mitigate them! FIX YOUR FUCKING PRODUCT.

Identify top contact drivers and drive long‑term solutions with Product/Engineering. — Support cannot fix your organization. This has "massive and ongoing failures of leadership" written all over it.

Implement improvements that reduce escalation volume and increase product stability. — FIX. YOUR. FUCKING. PRODUCT.

Expert-level understanding of AI for service management, implementation workflow, multi-tenant SaaS architecture, APIs, complex system integrations. — I don't know what this company is looking for, but it's definitely not a Director of Support.

Ability to professionally handle and resolve stressful situations will be required — That much is clear.

Professional appearance and presentation required. Excellent negotiating skills and ability to effectively manage internal and external relationships. Ability to influence, build relationships, understand organizational complexities, manage conflict and navigate politics — This company is un-fucking-believable.

I think it goes without saying, but this job is a Seriously, Maybe Don't. Genuinely one of the worst I've seen in a while.