I don’t think enterprise software is by definition bad. You can absolutely make good enterprise software, but doing that while adhering to the morass of requirements is a skill unto itself.

And something that most people in an enterprise are just not all that interested in, since they’re never judged on how pleasant the software they deliver is to use.

Hell, they not ever see any of the users interacting with the software. I’ve been at $ENTERPRISE for 7 years, and I’ve visited our users exactly once.

I was in Enterprise software and even though I didn’t visit users, I dealt with them regularly eg through video calls or engaging with them via support forum if support escalates an issue.

And yes we were judged on how pleasant to use our software was. If we miss a feature or ship a feature that customers intensely dislike, best believe that we’ll get a torrent of negative feedback on our support channels

In my experience enterprises do not want to pay for excellent software, simply because it is expensive. I would love to work on software that was:

- in more than two AWS regions

- required screen reader / disability support

- required multi-language support

- required multi-cloud

- actually needed a big Hadoop cluster - most enterprise data processing can be done on a MacBook Pro M4.

> in more than two AWS regions

As someone who has had to deploy services in every AWS region, of every AWS partition, I fantasize about two regions being sufficient.

My second major project at $ENTERPRIsE was 15 years ago and incorporated the first 4 (well multiple servers on different continents, why would I care about AWS)

It was internal shadow IT at its finest. It’s still used today, despite the people at the top not liking it the users think it’s the best thing since sliced bread.

Agreed. Another point IME is that the problematic requirements are also often non-essential, such as using a certain in-house framework made by some director, or building the whole project inside some abomination, like the workflow system of the Enterprise Content Documentation system.

This is how I’ve seen two-month projects becoming multi-year multi-team behemoths.

> Does "career development" just mean "more money"?

Big companies means more opportunities to lead bugger project. At a big company, it’s not uncommon to in-house what would’ve been an entire startup’s product. And depending on the environment, you may work on several of those project over the course of a few years. Or if you want to try your hand at leading bigger teams, that’s usually easier to find in a big company.

> Is it still satisfying if that software is bad, or harms many of those people?

There’s nothing inherently good about startups and small companies. The good or bad is case-by-case.

> Big companies means more opportunities to lead bugger project. At a big company, it’s not uncommon to in-house what would’ve been an entire startup’s product. And depending on the environment, you may work on several of those project over the course of a few years. Or if you want to try your hand at leading bigger teams, that’s usually easier to find in a big company.

Okay, so career development means "bigger projects"?

> There’s nothing inherently good about startups and small companies. The good or bad is case-by-case.

Well, maybe not, but I think the post illustrates some ways big companies are worse. I'd say that, all else being equal, companies tend to get bigger by becoming more doggedly focused on money, which tends to lead to doing evil things because you no longer see refraining from doing so as important compared to making money. Also, all else equal, a company that does something bad on a small scale is likely less bad than one that does something bad on a large scale.

projects beyond a certain size in a large org imply things which are very different - people, networking, money, regulations, politics, business, security etc all things which don’t look spectacular when you have three people, but become very important and much harder with hundreds of people.

So career development really means ‘learning a completely different skillset which is not technical’

That's a good way to put it and is something I've often thought as well, although not just in the technical realm. I think of it as "doing a different job". You used to be a teacher but now you're the principal; you used to hammer in nails but now you direct the construction crew; you used to be writing software but now you manage other people who write software; etc.

Personally I'd struggle to consider that "development" for my own life, since it often amounts to no longer doing the job I like and instead watching other people do it. I can understand how adding new skills is positive, though.

This can be mitigated by learning other technical fields ( infrastructure, security, etc ) and using your technical knowledge to steer things in the right direction - but yes, you’re otherwise right and I understand your point of view.

My experience at big companies has been that you only get the opportunity to do something big if you are willing to waste years "proving yourself" on a lot of tedious bullshit first. The job you want is not the job you get to apply for, and I've never had the patience to stick it out. Smaller companies let me do meaningful work right away.

Politely, I disagree. It means you are in a context where the risk aversion is high, everyone keeps their head down.

Done right, you can be a disruptor, for what are very benign or proven changes outside of the false ecosystem you are in.

I recommend these changes are on the level of "we will allow users to configure a most used external tool on a core object, using a URI template" - the shock, awe, destruction is everyone realizing something is a web app and you could just... If you wanted... Use basic HTML to make lives better.

Your opponents are then arguing against how the web works, and you have won the framing with every employee that has ever done something basic with a browser.

You might find this level of "innovation" silly, but it's also representative of working in the last few tiers of a distribution curve - the enterprise adopters lagging behind the late adopters.

The Freudian slip here is great.

> Does "career development" just mean "more money"? If so, why not just say "there are opportunities to make more money"? If not, what is "career development" that is not just becoming more deeply buried in an organization with the various dysfunctions described in the rest of the post?

In life, everyone that thinks a lot is eventually confronted with the reality that we're all just minor players within much bigger systems. When you follow this thread, pretty deep questions start to fall out like "how can I be just in an unjust society?". Or "what's the best way that I, as an individual, can have a positive impact on my community?". Or "Is there any point in trying to change systems given my small role within them?".

To these types of questions there's various different responses and consequences. Some people dive in feet first and engage heavily with the mechanisms they have to enact change (such as local politics, grass roots political movements, activism etc). Some people, overwhelmed by the weight of the system, disengage entirely.

Now to answer your question, I believe in the work that we're doing (or else I probably wouldn't have joined). Career development at the company isn't just more money (though that's obviously a component), it's being given more responsibilities alongside the capacity to enact more and more change.

Faced with a dysfunctional organisation that you're a part of, what do you do? The options as I see it are roughly:

- Change companies, and acknowledge that the dysfunction is insurmountable.

- Do your job and stay at the position you're in.

- Embed deeper into the dysfunctional organisation, with the view that you can be an agent for positive change.

>Is it still satisfying if that software is bad, or harms many of those people?

To some people, yes. There are people out there that take satisfaction in doing harm. Not me, nor do I believe the work I do is harmful. I didn't think I had to be so granular as to say "It's satisfying to write software I believe is a net positive to society used by millions".

Thanks for your thoughtful reply. I see what you're saying, although with the way the world is going, I'm increasingly doubtful of the potential of that approach, because it seems that companies are becoming more brazen about explicitly selecting for their narrow and immediate self-interest. In other words, the more you use your responsibility and influence to enact change, the more likely you'll just lose that responsibility and influence (i.e., get fired, demoted, or just shunted away to places where you can make less of a difference). However, that's not entirely the case everywhere yet, and it sounds like maybe you've found a place that's big but still not entirely evil, which sounds promising. :-)

In any case, I didn't mean to imply that what you're doing is any more objectionable than anything I or a zillion other people do when we make the same tradeoffs you allude to. What I was mostly reacting to was that you mentioned those things in the section on things you viewed positively, whereas they seem to me like they still incorporate a tradeoff involving a significant amount of badness. Perhaps though you simply meant they were tipped at least slightly toward the positive side on balance, which makes sense.

Sure, "It's satisfying to write software I believe is a net positive to society used by millions". But, if there was no increase in compensation, you would try to move up the corporate ladder?

I'm not trying to invalidate your post; I think your essay is great. I think it just does have enough cynicism. These $ENTERPRISE companies basically set up their employees some kinda game. There are certain rules (some written, some unwritten) for how you get a good performance review and how you get promoted. Just like there were dumb rules for you had to write code on a whiteboard to get the job despite the fact that you have never written algorithms ever, much less on a white board. So you have to balance how much you are doing something actually useful with jumping through whatever hoops that are downstream of whatever idea your VP has come up with this week. In the ideal case you move yourself to a part of the company that aligns with your values and interests so that the promotion comes easily, but sometimes it is easier to stay where you are and just grind through whatever absurdity it takes to stay employed.

People are motivated by status just as much or even more so than by money. Consider startup founders who eat ramen for years just for clout, or people who continue to pursue wealth long after marginal diminishing returns have gone to 0, that's about status.

> Does "career development" just mean "more money"?

If you want to become a researcher in data science or developper evangelist for instance, you'll need a org that can sustain your work.

Or if you want to be a micro service architect, you'll be booed in a 3 people shop but heartfully welcomed in 3000 people companies.

Same for engineering manager paths, it only makes sense if you have the headcount.

> software is bad, or harms

What you work on doesn't need to be Enterprise software. Hopefully it isn't.

> heartfully welcomed in 3000 people companies

Unfortunately, because most of those 3000 will think about the fact their org is 3000 people. Not that the user base for the new product is 5 people using it only on the weekend.

I’ve worked in a lot of enterprises on “tiny projects” but never on something that only went to 5 users. In one role I was the sole maintainer of a “small internal tool”…that had 1,000 daily users logging 5 hours/day each.

> if a piece of software is in any way described as being “enterprise”, it’s a piece of garbage.

if safety standards are written in blood then enterprise software is written in lawsuits

Disagree that it's written in lawsuits, it's written to please every customer under the sun and due to this, code base has become Rube Goldberg machine that few people understand.

> it's written to please every customer under the sun

Yes, with the caveat that the customer is not - nor does not represent - the actual end-users. The customer is someone in procurement.

...or nepotism is involved.

> it's written to please every customer under the sun

Disagree with this. In the places I’ve worked, I’ve lost count of the number of times we turned down feature requests with the explanation that - this isn’t common practice and seems to be unique to you.

I think you are one working at Unicorn. Most Enterprise software I've dealt with ends up with internal coding engine so it can be extended to do whatever the customer needs. Bonus points of getting to charge massive implementation consulting hours for all coders that come along during implementation.

> ... Remy's Law of Enterprise Software ... the list of good things at the end of the post.

Like the poster of the blog article, I too have worked in very large enterprise. Think 200K staff, 10K distinct servers, etc...

I had the lucky opportunity to assist the CTO in hundred-million-dollar enterprise software purchasing decisions. I got to interview vendor after vendor, grilling them to see if they're compatible with "large enterprise".

Most weren't.

This wasn't about some Kafkaesque hoops they had jump through while blindfolded and on fire, although I'm sure that's the impression most of them got.

The requirements were simple and perfectly sound architecture principles that they either met or did not meet. If they didn't meet them, then maybe their software was "good enough" for tiny clients, but would never work at scale.

I even made a list, which from memory was something like:

1. Support single-sign-on from external sources such as LDAP, OAuth, whatever. (We're not going to sync our directory and every user password to your insecure garbage software.)

2. Have some sort of audit log. Administrative or configuration changes especially. (Some places have hundreds of admins, not all of whom are fully trusted.)

3. Have an unattended installation process, even if it's just VM cloning or whatever. (I'm not clicking through your GUI wizard 500 times at 3am on Sunday morning.)

4. Allow incremental migrations/upgrades. I.e.: The "easy" process of stop-the-world; one-way-big-bang; start-the-world process is not viable in an enterprise with 10K tenants where the upgrade may or may not work for all of them on the first try.

5. Scale. This can be as simple as having indexes on "user" and "tenant" tables, which is easily overlooked when the typical dev works with a scale of 1 user and 1 tenant. Similarly, using combo boxes / drop downs is a no-go for most fields such as security groups. (We have 700K security groups. No, we can't delete 699.9K as a workaround to make your GUI not crash from an OOM error.)

6. Accessibility is mandatory. With up to 200K permanent and 1 million occasional users, every disability will be represented. Not just vision or hearing problems, but motor-neuron issues, amputees, etc... (You name it, we have someone on staff with it.)

Etc...

Seen in that light, Enterprise software starts to make sense. It's not baroque or malicious, it's just taken on a certain form to suit a purpose.

For example, I didn't understand why Active Directory uses search dialog boxes for every "picker" GUI control instead of a simpler drop-down or something similar... until I worked in an environment with 2 million objects in the directory.

> For example, I didn't understand why Active Directory uses search dialog boxes for every "picker" GUI control instead of a simpler drop-down or something similar... until I worked in an environment with 2 million objects in the directory.

And that’s when you realize that searching in AD is actually dog slow, and you are better off just syncing the whole thing to a proper database, then checking if the object still exists after.

Seriously, why does a search that takes 1ms in postgres take 3 full seconds in AD?

It's a very simple database engine, effectively the same as Microsoft Access but 64-bit and server hosted. The internal data representation is also sub-optimal because it uses a triplestore (key-column-value) to support LDAP schema changes without having to apply matching SQL schema changes. I don't believe it has any sort of full-text indexing capability either, it just uses ordinary sorted indexes. Hence, some search types are effectively table scans.

>Seriously, why does a search that takes 1ms in postgres take 3 full seconds in AD?

Because when specialization occurs, every specialized component (including people) is selected against performance and other non-essential metrics.

You shouldn’t have 700k security groups though. I know that you end up with that, but it feels like a sign of organisational disease (not that we’re doing much better, but the ratio is more 1 to 1, instead of 3.5 to 1

> You shouldn’t have 700k security groups though

The 700k groups also comes about when the security tools are all inter-operating at the wrong abstraction level. If a third party appliance needs to import all 700k of your security groups it means the appliance is performing authorizations itself, logging it differently than your other apps, and even make decisions based on stale data it's cached (you can't load all 700k groups on every request.)

This task should really be delegated to a dedicated authz system, too bad more of the world doesn't run on Zanzibar.

That was an eye-opening insight into enterprise software requirements. Thank you for sharing.

Great list. I remember being called in to look at software my company was thinking of buying, once... Only our finance/accounting people had looked at it so far. The thing barely worked. The desktop window kept flashing. Special characters were accepted and then broke the output. Extreme lack of features needed for the supposed goal.

I was able to find us an open-source / self-hosted solution that worked far better (bookstack). But I was amazed at how far the company selling the software got with us -- seems like most never get pushback, they just make sales by labeling themselves as fit-for-purpose regardless of whether or not they generally work.

> Is it still satisfying if that software is bad, or harms many of those people?

sadly many engineers might detach or feel powerless or simply not their part of the job, and only be attracted to the huge scale. sadly you can only ever work at that scale if you work for a few of the giants, of which mostly all do the same algorithmic dark patterns extraction methods shareholder benefit maximalism capitalism pushes them into

>> There are actual opportunities for career development. > Does "career development" just mean "more money"?

To me it seems it’s related to the specialist-generalist point that it’s easier to focus on one thing rather than to do all the chores you face in SME environments.

> Does "career development" just mean "more money"?

No. Career development includes paid training sessions, title promotions (junior -> senior, etc.) opportunities to work on larger projects in more significant roles (resume building), and opportunities to transfer into management, as well as (in some cases) opportunities to publish conference papers and the like. As you get older, this kind of career development becomes more important because it is recognized by people who will hire you.

> Does "career development" just mean "more money"? If so, why not just say "there are opportunities to make more money"?

That was not my takeaway, because earlier he alluded (twice) to the fact that titles are a thing:

1. A senior technical person who can't turn on a computer and an analyst not being able to speak english,

2. `I have met no less than 6 (six) people with the title "head of architecture".`

So I am guessing that is what he means by "career development"; you can acquire impressive titles.

I've never understood why anyone would care about titles at all.

> I've never understood why anyone would care about titles at all.

I cannot understand this sort of notion at all.

1. You don't care about $SOMETHING - great, I can understand that.

2. You don't understand why others care about $SOMETHING - Sure, I can understand that too.

3. You feel a need to broadcast this lack of understanding to the world - wtf?

I mean, I'm ignorant on a lot of subjects, but I hardly ever boast about my ignorance.

It's like when people proudly tell me "Oh no, I've never been any good at Maths": sure, lots of people aren't good at reasoning, but is being stupid something to brag about?

Aren't you doing exactly the same thing yourself? Your reply literally begins with the words "I cannot understand ..."

> Aren't you doing exactly the same thing yourself? Your reply literally begins with the words "I cannot understand ..."

Yeah, but mine was contextual; I replied to someone complaining that they can't understand. That reply was not contextual, it was simply virtue signalling.

Hint: he's not broadcasting a lack of understanding, he's boasting, posturing, that people who think titles mean something are dumb and he is too smart to be taken in by it. Ideas like "titles look better on a resume to future employers" or "titles make my extended family proud when they know nothing about my job or industry" or "bigger titles get a default level of respect from distant employees within the company" are lost on him.

It's not like when people tell you about their low maths ability, that's generally not boasting it's more trying to make a social connection. Like "I'm humbling myself and admitting flaws, not putting myself above anyone else (which would be rude)" or "you computer guy must be a math person, don't hate me because I'm dumb, please be kind" or "I've never liked <those> people, you're like me, right?" where <those> is book-smart people (or any <other_people> target group).

With more title comes more salary. Usually more ability to influence more policy too.

"More title" can also be used to quell ambitious, but naive/misguided people into not asking for a higher salary. I've met quite a few people who attach way too much pride to how "high" they are in the corporate ladder. They saw the title itself as a part of their compensation.

Commenting just on:

> > It's satisfying to write software used by millions of people. > > Is it still satisfying if that software is bad, or harms many of those people?

I work for a bank, so the software/service my colleagues and I deliver is probably at best "bottom of mind" for most people and at worst actively despised by many (maybe not even our specific implementation of it, but the idea in general that you depend on some behemoth to receive and send money).

Still it's very satisfying to deliver it, because if I mess up it's my mom that will no longer be able to pay for her online purchase or that large energy company everyone knows that can not pay out their salaries. What I do directly impacts people's lives in very practical and real ways. I would really miss that if I worked on some niche SaaS product with a few customers only.