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Had a busy weekend / Monday (all good stuff, just time-consuming), so Bad Job Bingo’s a little late tonight. Brace yourself for swearing at the end. I was trudging through the Careers page hell.

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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.

  • None this week.

Eh, It’s Probably Fine

A few flags popped up, but no serious ones.

  • Senior Support & Enablement Operations Analyst ($121k-$151k) at Docker (Remote US, CAN)

    • The Careers page is detailed and informative, although all of the employee testimonials on that page are from white men. Oops!

    • Hmm...Docker positions itself as a startup in this job description, which is odd since it's been around since 2013. I'm always a little concerned when companies can't seem to let go of a startup mentality, even though they're well past the age when they should be comfortable with more sophisticated operations.

    • The perks section includes medical benefits, which—say it with me—are not perks.

    • But! The job description is thorough and well-considered, and the pay is excellent, as are the benefits (among which are 100% company-paid for employees and dependents!). This is a high-ranking Eh, It's Probably Fine.

Tread Carefully

Didn’t quite hit bingo, but there were several yellow flags or more than one red flag.

  • VP, Customer Operations (No comp given) at Orderful (Remote US, CAN)

    • We're building a strong team of people who find purpose in their work and support each other in the process. At Orderful, you'll have the opportunity to work with like-minded people, the autonomy to tackle challenges, and truly make an impact. — It's not that I hate this company intro, it's just that it's so generic. I swear I've read this on a hundred other Careers pages. It's the plain white bread of company pitches.

    • Their Values are decent, if basic, but I do like that they included this bit (positive cultural signal!): We provide a safe environment to learn and try new things.

    • Seems like they have a diverse team (even in technical departments), and their testimonials are very sweet and people-centered (I also like that they took care to make sure the testimonials weren't just from white dudes).

    • So I think this might be the first time I've reviewed a VP, Customer Operations and a Director, Customer Support from the same company, so I'm excited to see how they compare.

    • Orderful is reinventing how businesses connect and trade. — Isn't everyone?

    • Our culture is high-ownership, high-tempo, and low-ego - we iterate quickly, care deeply about customers and teammates, and love turning manual operations into products. — Two startups in a row that didn't use "fast-paced, startup environment"?! I feel both overjoyed and deeply threatened. If this keeps up, will the jobs even need me anymore??? Who am I without yelling about lazy companies? FRIENDS, WHAT WILL I DO?

    • Genuinely love the Opportunity section and the very transparent explanation of what the role will need to accomplish in the next 12-18 months. It seems perhaps a little too ambitious to me, but at least the goals are appropriate for a VP, and you know the score going in and can decide if it's something you're willing to tackle.

    • Testing & Quality – Modernize testing frameworks and leverage automation to ensure reliability and speed. — This is from the What You'll Lead section and seems out of scope for a VP, Customer Operations, but maybe they mean CX quality?

    • Integration & Automation – Oversee ERP and system-of-record integrations (e.g., NetSuite, D365 BC, SAP B1), and evolve service delivery into repeatable, automated experiences. Partner & Vendor Programs – Develop and manage a global network of certified delivery partners to augment capacity and maintain quality. Retail Partnership - setup and scale strategic retailer partnerships with major players like Kohls’, Target, Walmart etc. from POC to scale These also seem like out-of-scope teams for this kind of role, but maybe that's just me!

    • Love that they included a What Success Looks Like section for the same reason I liked the Opportunity section, and the role requirements are reasonable. The About Our Work Environment bit strays dangerously close to a few BJB entries, but given their overall transparency, I'm willing to give them a pass.

    • I think this sounds like another cool opportunity, although I'd ask about the scope of the role, given that at least a few of the teams they'd be overseeing are often separate departments.

    • However, yet again, what would otherwise be a solid Eh, It's Probably Fine is getting thrown into Tread Carefully instead because there is no comp given. I guess I have job security after all?

    • Edit: I heard from a reader that Orderful has posted some version of this role several times (and that they’d applied for at least 3 recently). Seems like it could be a 👻 Ghost job!

  • Director, Customer Support (No comp given) at Orderful (Remote US, CAN)

    • See the VP, Operations role for notes on the Careers page.

    • There are some weird formatting issues in this job description that weren't present in the VP role (very tiny font in the first three sections of the JD). It could be that the hiring manager is stretched thin, or there's no People Ops to speak of, as I'd like to think they would have caught this.

    • Compared with the VP, Customer Ops role, it's clear that much more thought and effort went into the VP JD. Each section is more abbreviated, and there are no The Opportunity or What Success Looks Like sections. In terms of transparency, this JD suffers without them.

      This role does get a Why work with Orderful? section that was not in the VP role, but oddly, I think the addition hurts them rather than helps:

      • Competitive Compensation — I'll let you guess why.

      • Lifestyle Work From Home Benefit, Remote Work, Flexibility — Yes, you're reading that right: three separate bullets that say basically the same thing. It's like a Greek chorus of things that are not benefits.

      • Weekly Yoga — This is a remote position.

    • Having said all that, this role's responsibilities are well-scoped and make sense for a Director role, as do the requirements, which distinguish it well enough from the VP position.

    • The application also does an interesting thing: it offers prewritten options to indicate your experience level for various requirements, which I think is a neat alternative to having candidates write essay responses.

    • If it weren't for the lack of salary transparency, this would still go in Eh, It's Probably Fine, but alas. You know the drill.

  • Global Support Manager (No comp given) at Unstructured (Remote US)

    • No real Careers page to speak of, and given the company obviously dropped a decent amount of cash on their website, I don't really understand why there isn't one (or an About page that at least introduces candidates to the company).

    • We’re hiring a Global Support Manager to build and lead Unstructured’s global customer support function from the ground up. This is a true builder role: you’ll design the operating model, hire and develop small, high‑impact regional support teams (initially ~2 engineers per region across the Americas, EMEA, and APJ), and establish the processes, tooling, and culture needed to support enterprise customers running mission‑critical AI and data workloads.

      • This is a fantastic introduction to the role, and it's a green flag that they included building the team culture as part of the role. Having said that, even though it sounds like this company is still in startup mode, given these duties, this role really should have a more senior title – Head of Global Support at least, but I'd prefer VP, just to give them similar seniority to other senior leaders they've likely already hired.

      • I'm also concerned that they don't mention hiring managers – even at just 2 per region (assuming they don't mean only the three they mentioned, since those cover a lot of time zones), they're going to hit the limit on how many people one person can manage almost immediately.

    • You will balance strategic ownership with hands-on execution—setting the long‑term vision for global support while remaining close to customers, incidents, and escalations. — Again, I like this, but there really needs to be a layer of management between this role and the direct support team; otherwise, they'll spend a lot of their time filtering their inputs down to just the things they really need to be hands-on with.

    • Review and evaluate existing support tooling (e.g., ticketing, on‑call, knowledge base, customer communications). — Okay, so maybe there's already some kind of team in place? It's not clear, and I think it would benefit them to be more explicit about this (also, if there is already a team in place, the title is even more confusing).

    • 8+ years in customer support, technical support, site reliability, or customer engineering roles within an enterprise SaaS environment. — Yeah, this really needs a more senior title!

    • A hands‑on, builder mindset: comfortable operating without heavy structure and creating clarity where none exists. — I really do love this phrasing—again, see how you can describe the skills and culture fit you're looking for in a candidate without resorting to tired and easy tropes?

    • Why You’ll Love This Role — Appreciate this positive, candidate-first framing!

    • Damn, I think this would be a high Eh, It's Probably Fine if it had salary transparency, but it doesn't. That's a big bummer, because despite the titling issues and ambiguity about the existing team, I think there are a lot of positive cultural signals, and it would be a fun, meaty role for someone who loves the swift pace and depth of skill / knowledge that one gets to apply when building a Support function for a startup. I reluctantly place this in Tread Carefully.

  • Senior Support Operations Analyst ($130k-$150k) at Babylist (Remote US)

    • The Careers page brags about being a top place to work, so...off to Glassdoor!

    • You ever read Glassdoor reviews and think the high-scoring ones are definitely either HR or the result of HR begging employees to go give them high marks? That's the feeling I get with Babylist's reviews. Even the good reviews say things like:

      • "Your tenure (Months/Years of service) starts all over [when you promote], which means your actual pay could actually be dropped and it make take 2 years to get to that higher pay than the previous job. However, this means many just stick to their lower pay rates at a higher step level just to keep from their pay dropping, which management evidently want it this way to save on money."

      • "Don't work at Babylist if: You can't handle a direct communication style from leaders. They won't hold back to tell you what they think is good and what they think is not. I think that makes our product and business much stronger, but it's not for everyone. You don't want to work hard to meet high expectations. We hire the best, we build to a high bar... you'll be surrounding by amazing people and be accomplishing awesome things. But the expectations are high! Babylist is fair and work-life balance is fine, but it's not somewhere you can rest and vest."

      • So...yeah. Do with that what you will.

    • At Babylist, we embrace a high-performance culture that values direct feedback and a growth mindset. — They buy Radical Candor for every manager, don't they?

    • We're excited to welcome new perspectives to our team. — Am I surprised that there's no diversity statement on their Careers page? No. No, I am not.

    • All full-time, US employees receive a generous Babylist Shop discount. — Yeah, that checks out.

    • Thrives in dynamic, evolving environments, adapting quickly to new information and leading teams confidently through ambiguity — So that's two BJB red flags and a reference to leading teams in a job description that doesn't say anything anywhere else about leading anyone. Efficient!

    • Thrives in fast-growing scale-up environments (vs. large enterprises) where you build processes from scratch with limited resources and navigate ambiguity without clear playbooks — Nevermind. This is not efficient, but it is a big red flag neon sign!

    • The rest of the JD is fine, and the pay is great, but there are enough worrying cultural signals and other red flags that I feel compelled to put this in Tread Carefully. However, the pay is good enough that, for someone going in with their eyes open, it could be worth it even with the flags.

  • Senior Manager, Enterprise & Strategic Support ($128k-$176k) at Checkr (Hybrid US-Denver, CO; Nashville, TN)

    • Premium Support Programs: Design and implement differentiated support offerings for enterprise customers, including dedicated support models, enhanced SLAs, and white-glove service programs — Ehh, this feels like something the Director of Customer Support should handle with input from this role, but again, maybe that's just me.

    • Direct management experience leading teams of 10-20+ support professionals in high-growth environments — This is way too many people for one person to manage. If Checkr wants candidates to have experience managing managers, they should say that.

    • The rest of the job description seems fine. And while the pay is good for this role, it isn't for frontline roles, which pisses me off, so into Tread Carefully it goes.

    • Another first, I think, with this company: we also have access to a frontline role job description in addition to Director and VP-level roles. Pretty cool!

    • This JD has the same problems as the Director role: weirdly tiny font and an unintentionally amusing Why work with Orderful section. (Also, I think maybe the font fully changes for some of the bullet points later in the JD?)

    • As a Product Support Analyst, you’ll bridge the gap between modern API technology and global supply chain standards. — I genuinely do not know what this is supposed to mean.

    • You will triage and resolve technical questions through our ticketing system, acting as a subject matter expert for our cloud-based EDI platform. Your mission is to deliver fast, accurate support while building the knowledge base to help our support scale. — This, however, is a great, straightforward description of the role.

    • To support close collaboration with our EU partners, this role works a 4:00 AM–1:00 PM ET schedule. These hours are a core part of the role, so we encourage candidates to consider their ability to commit before applying. — I think it's good they're upfront about the schedule expectations, although I'm curious why they don't just hire someone in an EU time zone. I get that a lot of startups don't have the tax setup/hiring infrastructure to do that yet, but like...Deel exists (for better or worse).

    • Unusually, we do get comp for this IC role and not for the senior ones: The pay range for this role is: 73,000 - 92,000 USD per year (Remote (United States))

    • But given the unusual schedule expectations and the very specific technical skills and experience required for this role, that salary range is not great. I mean, with the poor job market, they'll probably be able to hire someone at that comp, but yeah. I'm not impressed. Tread Carefully.

BINGO

Welp.

    • See the Senior Support Operations Analyst role for info on Babylist's Careers page.

    • This role reports to the Chief Product Officer, which is fine. But why not have a Chief Customer Officer (or make this role that) instead? Why must customer-facing roles always be junior to the rest of the senior leadership team?

    • Served as an executive and company leader, trusted to bring clarity and alignment across Product, Engineering, and Operations — So Support is expected to run the company. Cool cool cool cool cool cool cooooooooool.

    • Represent Support and RCM at the executive level, influencing company strategy, aligning priorities, and ensuring operational decisions reflect Babylist’s commitment to We Love Our Users — How is this role supposed to do any of that when every other executive outranks them?

    • Again, pay is great, but I dunno, man. You'd be putting a lot of faith in the goodwill of people who can fire you if you don't somehow influence them to run the company properly. I'm calling BINGO on this one.

  • Customer Support Specialist ($35k-$44k) at Checkr (Hybrid US-Nashville, TN)

    • Grit - We are passionate and hustle to raise the bar. We persevere through our challenges and grow from our failures. — There's a part of me that wants to BINGO out anything that mentions hustling. I won't. But I want to.

    • I do like their hiring philosophy, though. Green flags there.

    • This might be the only company I've seen that brags about being a great place to work, and the Glassdoor reviews reflect that (and seem pretty balanced regarding pros/cons). Refreshing!

    • Demonstrated resilience, self-management, and commitment to continuous learning and improvement — Woof.

    • What You'll Get - A fast-paced environment — Ooh, just what I always wanted!

    • opportunity for advancement — That's not suspicious at all.

    • Hourly Pay Range (Nashville, TN) $16.83 - $21.16 USD — This pay sucks. And for a hybrid role, it sucks way fucking more. BINGO.

Seriously, Maybe Don’t

Don't say I didn't warn you.

  • Customer Support Specialist (Product Expert) ($56k-$84k) at Klaviyo (It Is A Mystery-Denver, CO)

    • This is the first thing you see when you hit the Careers page:

    • Building for 183,000 businesses isn’t easy—and it’s not meant to be. Klaviyo is intense and demanding by design. — <nervous laughter>

    • But if you thrive on challenge, the reward is well worth it: accelerated growth, real impact, and work that truly matters. — Because only working on a CRM platform truly matters. Nothing else, like putting out house fires or curing cancer. Just working on Klaviyo.

    • Your favorite brands’ favorite platform The brands you know and love? Chances are, they’re powered by Klaviyo. Here, you’ll be part of what keeps those brands growing and connecting with millions of people every day. — Look, I know some people care about this. I am not one of them, and when getting to things like actual benefits takes scrolling almost all the way to the bottom of the Careers page, I'm gonna call you fucking ridiculous. Because it's fucking ridiculous.

    • Three promises we make to every Klaviyo: You’ll do challenging, meaningful work—pushing boundaries, driving growth, and creating lasting impact. You’ll work with ambitious, bold peers—bar-raisers who inspire each other and do work people rave about. You’ll work on an inspiring mission—empowering creators to own their destiny. — Not, we'll take care of you. Not, we'll grow your career. Not, we'll pay you well. Nope! Just "you'll devote every waking moment and all of your energy to making Klaviyo money." How kind. How motivating.

    • Explore the CRM built for B2C A single platform for marketing, service, and analytics—designed to help consumer brands deliver personalization and growth. — Yes, this is still the Careers page. We have not wandered off onto the Product page. We're still here.

    • We prioritize our customers > customers’ customers > team > ourselves. — Oh, believe me, that's very clear.

    • AI is in our DNA — Still on the Careers page.

    • Recognition feels good. Working here feels even better. — Oh, is that right? I'm sure Glassdoor will reflect that!

      • "Ticking bomb" (2 stars)

      • "Completely Nosediving" (1 star)

      • "Toxic place" (2 stars)

      • "Toxic culture shift" (2 stars)

      • "Unfortunate senior leadership" (2 stars)

      • "Cool people but uphill battle for comp" (1 star)

    • Ambition without borders – More than 183,000 brands count on us to move faster and grow smarter. With teams distributed around the globe across regional hubs, we earn that trust every day by building tools that strengthen customer relationships and deliver real results. — WE ARE STILL. ON. THE CAREERS PAGE.

    • Perks with purpose — Finally, this Careers page put me out of my fucking misery, THANK YOU DOG

    • I don't even remember which job I was supposed to be rating. Goddamn.

    • Oh right, Customer Support Specialist. I'm sure this will be fine.

    • At Klaviyo, we value the unique backgrounds, experiences and perspectives each Klaviyo (we call ourselves Klaviyos) — Of course you do.

    • We are very interested in individuals who have a track record of finding creative solutions to unique problems, who thrive in challenging situations and want to apply these skills to solve for customers using our software. — What about providing support for CRM software is a challenging situation, fucking hell.

    • Capable of adapting quickly to changing priorities — Sure. Why not.

    • So the low end for this role is way too low, and the high end is just okay, although I'm not sure any amount of money would be worth braving this mess. It sounds like literal Hell.

That's it for this week! If you have jobs for Bad Job Bingo you'd like to submit, you can simply reply to this newsletter email or submit a job here (here are the BJB FAQs in case you have questions).

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