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Two Years Working at Dropbox (chadaustin.me)
95 points by slyall on Dec 7, 2019 | hide | past | favorite | 76 comments

Seven managers in two years. I can’t accept that as some great thing which works and makes sense in any combination of letters and numbers.

I’ve been a happy Dropbox customer for years and I was happy to pay the recent price increase in return for more space... but I can’t help feel that the company has been burning a lot of investment doing random stuff that I don’t care about, while core features go neglected. My pet peeve example being: why does Camera Uploads not upload Live Photos from my iPhone? Google Photos manages to do it.

> So I was shocked to find that running an empty Python unit test at Dropbox took tens of seconds. Worse, when you fixed a bug and landed it, depending on how the daily push went, it might make it to production within a day? Two? Maybe more?

Is it just me, or does this seem like an extremely aggressive release mentality and set of expectations? Most places I'm aware of might do 2 or less a week, sometimes once a month. This engineer is complaining it took a day to release some sort of bugfix? Are most engineers and companies in 2019 operating like this, where is their time for a dev and QA cycle first? A unit test is only as good as what you wrote it to catch, real life bugs slip through unit tests all the time.

Every Bay Area company I’ve worked for(except 1) does not have QA. It’s expected by the time the dev merges it it’s been appropriately tested and can go straight to prod, so no need to wait. Fewer, smaller releases is generally better when something does go wrong as well, it’s more obvious which change is the problem.

The one that did have qa, the devs were incredibly lazy about testing, relying entirely on someone else to make sure it worked. I’d say the overall product was better with qa but the point at which a developer called it done was way worse.

Its quite interesting how different software companies treat their releases. At my job we have major releases twice a year, and patches a couple of times between those.

We can have a bug discovered, patched, tested, validated, and deployed same day. If it is small. Usually a bug may or may not make it in this sprint depending on criticality. Then we will fix it in some number of days, qa the next day and deploy that same day. Multiple deploys per week or even day happen on my team.

I wonder if the IPO related issues mentioned are common.

Specifically having half the senior engineers quit because they are now rich while some others become "underleveled" due to stock price falling 50%.

it's a sign of a poorly run company, not a symptom of the IPO per se.

An interesting read, for sure. I can’t shake the feeling that it is sanitized. Like every criticism is minor enough and outweighed with positives that I feel like it isn’t 100% honest. I don’t know if it’s a legal thing or a cultural thing or a “tell-all-isn’t-worth-risking-my-future” thing or some other thing. I am very sensitive to these kinds of things though. I have a critical East Coast mentality and I’m not a fan of West Coast yesism.

> a critical East Coast mentality and I’m not a fan of West Coast yesism

As someone who have no idea what this refers to (I'm not from the US [I'm assuming East/West coast here refer to the coast's of USA]), could you expand on what this means in reality?

I'll bite - I'm from the east and the business culture here drives me nuts. I've lived on the west coast as well, there are parts of the culture out there that drive me nuts but I much prefer to work with west coast/mid west companies.

East coasters believe themselves to be more realistic and pragmatic than west coasters, I often hear things like "oh yeah that's just a pipe dream that's not how real business is done", or "They're not thinking it through, I have x years of experience, and can tell you it can't be done". The worst part is that it has morphed into a bit of a superiority complex that dismisses innovation. There's just a lack of interest in trying to improve/change procedures because people feel so caught up in putting out fires and being busy in an attempt to look productive. It's absurd. And extends all the way to benign things like dress code. People are afraid to wear jeans at work because it might look "unprofessional" or like they're not working as hard as people who wear 'business' attire.

Yes I said dress code... I just left a job because of this exact old school east coast culture. The tipping point for me was that I received an email that was titled "Jeans in Jeopardy". Unless 90% of people or something donated to the cause we were going to loose our month of permission to wear jeans. I found that email patronizing and down right insulting and decided right then and there that I was leaving. If you trust me to write software that is handling business critical procedures... why don't you trust me to dress appropriately in the office? You can have you're dress code, I'm going to spend my time thinking about software instead of dry cleaning my shirt and pants every day.

> People are afraid to wear jeans at work because it might look "unprofessional" or like they're not working as hard as people who wear 'business' attire.

That just sounds like a bad company, not an east coast problem. I've worked at two NYC trading firms, and the typical attire is shorts and sandals.

> People are afraid to wear jeans at work because it might look "unprofessional" or like they're not working as hard as people who wear 'business' attire.

Is this the case in tech jobs?

In ~15 years of working in tech companies I don’t think I’ve ever not worn jeans; I reserve not wearing jeans largely for weddings and funerals.

Dress code is a weird one for me. I wish society, and businesses in general wouldn't make such a big deal about how you show up to work. Honestly as long as its appropriate wear, it should be fine. My manager wears slacks and tucks in his shirt, and I'm walking around in a hoodie or t-shirts.

As long as that’s not why he’s the manager.

I'm from the US and have no clue what this means.

There are some fairly large cultural differences between the East and West coasts. Having grown up on the East coast, places like Portland and Seattle feel as different to where I live as Dublin or Glasgow. But certainly not as different as Munich or Quito.

But I think a lot of the difference is self-fulfilling. If you grow up in one place and don't like it, you move. I grew up in a rural town, very conservative. I went to a local university. My first jobs were in the area. And I couldn't stand it. I eventually found out that, if you're uncomfortable with casual racism and anti-intellectualism, you just move away. Certainly the same thing happens in other areas, for anyone moving away from their local "culture". For me, that move was only 2 hours away to Northern Virginia, where I can still see my family, make it out to the public nature reserves I grew up with, don't have to sell my collection of guns, everyone has a degree, and people hide their casual racism a little better.

Don't get me wrong, there is shit I can't stand about this place either. But that's every place. I can ignore the problems of here a little better than the problems of back home. For whatever reason, I find it easier to ignore elitists who look down on folks for having "only" a Bachelor's degree than I can ignore luddites who feel threatened by folks who went to college at all.

+1, this is not a thing

The top response is a good reflection of my thoughts after numerous visits to the West Coast.


Edit: these are opinions outside of the context of software development companies.

According to the answers on Quora, the main difference between the east coast and west coast is that east coasters like to write long diatribes on the superiority of their region.

While trying to set up a Kafka trap you have fallen into one yourself.

That quora answer was a little uncivil, but not directed at any individuals. Similarly I don’t intend my sharing of it to be an attack on peers. If I’m being told I’m somehow at fault for sharing my thoughts when asked, isn’t that kind of validating my point of view?

Don’t take it personally, I was talking about all the other responses too. Weren’t you accusing the west coast of being overly sensitive?

Not at all. I like it when people are sensitive. To me that's in the same vein as being thoughtful and mindful of others.

New York business interpersonal style is blunt directness to power its capitalist effectiveness brand.

West Coast business interpersonal style is affirmational consensus to protect its “California dreamin’” brand.

Of course there are communal collectivist companies in Brooklyn and radical candor competitors in San Diego, but overall the two styles are different enough it can be difficult to integrate as a transplant.

// Disclaimer: bi-coastal tech entrepreneur since mid-90’s

Are you sure that difference is not based more on how old the businesses are than where they're located?

Yes, I’m sure.

Same contrasts between 150 year old banks, or between 150 day old startups.

// “The walls smell of Slack DMs and conflict avoidance.”https://aphyr.com/posts/342-typing-the-technical-interview

Hi, author here. Sometimes it's just like that. I loved my coworkers. I am (was?) bullish on the company. I thought they were doing a lot of great things. But there was plenty to improve at.

It was a confusing experience for myself and ultimately I quit of my own accord and found a job I was happier at.

> Dropbox only onboarded new employees every other Tuesday. This left me without health insurance coverage for a week between jobs. Fortunately, none of the kids got hurt that week.

This is just insane. I suppose people in the US are so used to this being "the way it is" they're desensitized, but from the outside perspective of the civilized, developed world, this is insane.

You started an off-topic flamewar with this comment. The site guidelines explicitly ask commenters not to:

"Eschew flamebait. Don't introduce flamewar topics unless you have something genuinely new to say. Avoid unrelated controversies and generic tangents."


The classic flamewar topics are like black holes that suck in everything that comes close to them.


Topics this generic never produce unpredictable discussion—doubly so when they're also divisive and inflammatory, which most are. On HN we want intellectually curious conversation. To get that, we need topics that are specific and unpredictable, not generic and well-trodden.


It is absolutely beyond the pale for the healthcare access of someone and their family to be linked to their employment. It perverts the freedom of movement between jobs that people have a fundamental right to.

I'd love to hear from Americans on the matter. Have you ever made career choices based on the effects it would have on healthcare coverage? Have you ever tolerated a bad job or bad employer because of access to healthcare coverage? Have you ever decided _not_ to take a risk starting your own small business because of loss of healthcare coverage? Have you ever had a family crisis and through it been forced to continue working in order to keep healthcare coverage?

I'm sure there are an assortment of remedies, but the fact that access to healthcare _EVER_ factors in to your career is manifestly wrong.

> It perverts the freedom of movement between jobs that people have a fundamental right to.

I was always fascinated that the US simultaneously had this health care system, and also a cultural obsession with small business (this may have faded over the years, but was a huge talking point in the 90s and noughties, especially on the right).

“People should start small businesses! Oh, also, if you do that you may die” was just such a perplexing message.

Being from a developed English-speaking country, where we get a lot of American media, it’s very easy to just assume that America is pretty much like a bigger version of what I’m used to. Until it comes to the jarring, utterly alien things, like healthcare.

> but the fact that access to healthcare _EVER_ factors in to your career is manifestly wrong.

ABSOLUTELY. I should be able to independently choose my healthcare coverage. I purchase my home/renters insurance, my car insurance, my liability insurance, my life insurance, etc. separately from my employer. Why not health insurance???

Employer-tied health insurance is literally federal law in the U.S.

It still boggles my mind how widely supported the ACA employer mandate ("Obamacare") was by my fellow Americans.

And disappoints me that the mandate wasn't repealed in 2017-2018 when it appeared the right politicians were in place.

The widely supported aspects of the ACA were guaranteed issue and the elimination of low quality plans (which really were pretty useless as insurance). Those things cost a lot of money and forcing employers to pay into the system (think of the mandate as a tax) is one of the ways they were paid for.

It's fine to not like it, but it was probably one of the less disruptive options for collecting more health care dollars.

As far as I can figure, there's really only 2 paths forward for the US system. Dump more money into it or train lots more providers. People don't seem to think we are short on doctors, but the market looks sort of exactly supply constrained, where everyone is busy and prices go up up up. Of course, because we are stupid, some of the most significant healthcare regulations...limit supply.

> think of the mandate as a tax

It's not a tax though. It's finding, choosing, paying for a particular insurance plan for their employees.

Thus, insurance being tied to employment.

Okay, I didn't really address that. I would argue that it didn't change the situation that much, because the situation prior to the ACA was that being in a group plan (employer coverage) was the best way for people with significant medical needs to maintain insurance.

For many people, "A good job" has long been one that came with health coverage (and given the expense of insurance, this continues to be the case).

It would be excellent for us to have a situation where people bought their health insurance individually. I think requiring more employers to provide insurance probably was an incremental step in that direction, as counter intuitive as it is, because it addressed the situation that existed in an achievable way.

My last job's insurance plan cost me $800/mo (family) just for the pleasure of having. Even with the insurance (which changed half way through employment) things like my migraine medication was still $150/mo on top of that (before the change it was not much).

This was actually much better than the job before that because at least the company paid for my coverage (may be confusing but that's still $800/mo out of my pocket to cover my family).

So yes, just the job you choose can be rather drastic changes in take home pay due to insurance coverage, so a huge impact on what companies you decide to work for.

You can imagine the headache each year when it comes time to have to choose insurance plans again.

On that migraine medication... all insurance companies limit the amount I can receive each month the a number much fewer than the migraines I get.

These migraine meds expect that you take it on the onset of the headache, often before you know it's even a migraine otherwise they don't work. So you are left with this decision, do I possibly suffer for the rest of the day or use up my stock for something that may not need it.

Worst part about it is, when you get that yearly headache from dealing with insurance plan renewal, you have to pay full price for the headache medicine because your deductible and out-of-pocket counters reset to zero!

Adding insanity to insult and injury.

As an Americam, I'm free to move about, but I don't move jobs very often. I consider healthcare benefits when I move, but only that I have them and that my new salary pays for them completely. If the new employer pays a smaller percentage of my healthcare bill, then my salary must increase by that amount. I've never switched jobs and had my overall salary decrease.

I wouldn't stay in a bad job for the benefits, but I'm a technical employee, who happens to have lots of choice.

I have had to choose between working at a fast food restaurant (crappy job) and working as a math tutor (awesome job), but the tutoring gig was a contract deal and as such they were not required to provide any health benefits. Working as a tutor for a couple months was really great, but in the end I had to go back to working fast food so that I can pay for medications and a surgical procedure. Yay Capitalism!

So on the topic of healthcare linked to employment, what would it have looked like if you took some of the tutor money and bought your own healthcare?

I want to say that maybe the fast food job simply paid more if you factored in the healthcare, but maybe it's that the fast food company can get way better insurance rates than you alone?

You are right, it comes down to the bargaining power of large corporations. The hourly rate of the tutoring gig was higher, but I would also have been paying a lot more for insurance, so it would even out. I also have to take brain medications which complicates things, because a lot of insurance plans don't provide good mental health care coverage, adding a layer of complexity to my decision making process.

For example, even if plan A and plan B cost the same amount out of my pocket, but Plan B does not cover my medications until after a $5,000 deductable, it really isn't helping me because all of my medications added up over a year come to just under $5,000.

There are so many layers of bureaucracy and complexity and institutional inertia keeping this exploitative system moving, it really needs to just be burnt to the ground so we can start fresh.

"It is absolutely beyond the pale for the healthcare access of someone and their family to be linked to their employment. It perverts the freedom of movement between jobs that people have a fundamental right to."

It's not really linked to employment. Employers pay for it, yes, but anyone can go on the open market and get their own insurance. I'm a consultant and have been paying for my own insurance for me and my family for a decade.

In addition to this, there's something called cobra, that allows you to pay for health insurance for awhile after you leave an employer. Unless the person in this article went over a year between jobs and never even tried to buy his own insurance, his lack of coverage is an exaggeration.

"I'm sure there are an assortment of remedies, but the fact that access to healthcare _EVER_ factors in to your career is manifestly wrong."

It really doesn't. The majority of companies provide healthcare for their employees. I've even worked for a company of 10 people and had fantastic healthcare.

"Have you ever decided _not_ to take a risk starting your own small business because of loss of healthcare coverage?"

No. You can pay for your own insurance, which includes doctor prescription, checkups, and you won't go bankrupt in an emergency (or paying for the insurance).

"Have you ever had a family crisis and through it been forced to continue working in order to keep healthcare coverage?"

Even if you have 0 coverage, a hospital will be forced to take you. If you get bills, you can negotiate with the hospital and you can get your bill down 90%. There are some nonprofits that will actually pay your bills for you if you really have no money.

Most of these articles are FUD to push everyone to go to Universal healthcare. Sure our system has problems, but a government takeover will not solve the issues.

Insurance was never meant to be used for everything. We need to get rid of the insurance companies and allow hospitals to actually charge patients the true value of things (which would immediately bring the costs of most things down).

Surgeries and procedures that happen often would be brought down due to competition and the ones that don't happen that often could be covered under some sort of insurance.

Platic surgery and Lasik eye surgery are good examples of this in action. A decade ago, they were both very expensive. Competition has brought the costs down considerably. My parents both got Lasik surgery without insurance and paid under $1000. 10 years ago, it was $10,000.

I also really never got the 'not being able to start a business' mentality. Sure you have more risk, but it will take you much longer to actually have a running business if you have an increased amount of taxes due to universal healthcare.

In most European countries, you need to involve the unions after a certain amount of employees. This combined with large amounts of taxes impedes growth.

I would be interested to see how many larger companies in Europe actually started and grew there or grew large in another country and then opened up an office/location there. I'm guessing more of the latter than the former.

I appreciate the thoughtful response. I have a lot to say on the matter but it goes well off-topic of, "healthcare shouldn't be bound to employment". However, I am curious. Technically, yes, you can go get your own healthcare and reject the employer's offerings? Is that a real-world practical option that people can and do opt to take?

Yes. Tons of people buy their own health insurance in the US. I have done so for my entire adult life.

Is it basically equal cost to the insurance most companies would be providing access to?

I have no way of knowing. I’ve never had a job that provides insurance. And I think most jobs do not break out the portion of compensation that pays for health insurance.

It seems like you're ignoring a lot of facts and making rash generalizations to justify your political position. In particular, this is stood out to me as blatantly wrong:

>You can pay for your own insurance, which includes doctor prescription, checkups, and you won't go bankrupt in an emergency (or paying for the insurance).

I know somebody who got in a car accident out in the hilly area of town, had to be airlifted to a hospital, and have his skull and spine reconstructed. The guy's a doctor who runs a private practice and he was buying his own insurance, the insurer decided what they were going to cover and what they weren't going to cover, and now he is literally 2 million dollars in debt (2 occupants in the car). And that's somebody who makes a hell of a lot of money compared to fast food workers, who are equally likely to get in car accidents!

You are either naive or fooling yourself if you don't see that this system is broken and exploitive.

Something is not adding up here. Health insurance in the US has annual out of pocket maximums that would have limited his total payments for the incident and all subsequent care to something like $15k/year for his entire family.

Only if they approve it and assuming the doctor takes your insurance. They may not approve it because you are out of network, they deem it not medically required or a drug that they will not pay for because there is a generic.

FWIW: yes it sucks, but in this instance you are allowed to retroactively purchase cobra insurance for several months after leaving a job. This means you get the same discounted rate that your company pays for their insurance. So OP had about 3 months to purchase this, even if someone got sick or hurt before he purchased it, OP was covered in this specific instance. You can continue to purchase this for up to 18 months.

> This left me without health insurance coverage for a week between jobs...I suppose people in the US are so used to this being "the way it is"

No. Actually we are not used to that being the way it is, the US has had a solution in place for this very problem since 1985 [1,2] - it's called COBRA and it extends your health care coverage after you leave a job that provides it.

Make no mistake - you pay for it. But by US employment law, HR is required to inform you about how to get COBRA to continue your health care coverage after you separate.

So author either had a company violating labor laws - or he declined COBRA coverage.

1 - https://en.wikipedia.org/wiki/Consolidated_Omnibus_Budget_Re...

2 - https://www.dol.gov/general/topic/health-plans/cobra

It's very expensive but you can purchase it retroactively - so don't have to pay for it unless you actually need to pay for medical expenses during the gap period.

One catch, COBRA is oy for companies of a certain size.

I'm lucky to be European. I can sleep well, since almost everybody got their basic health care need covered by our system. About 15% of my income goes into healthcare provider - once I am registered, I can use almost any facility available (doctors, dental, traditional or even some alternative medicine approaches, ...), if required.

The system is not even that complicated. I am not sure what holds the US back to have a humane care system.

Most European countries modernised their health care systems at some point in the chaos of the early 20th century, typically shortly after ww2. It was a time of huge social upheaval anyway. The current culture is less tolerant of sweeping change to how things are done.

FWIW, I pay way less than that for health insurance an an annual basis. Even if two members of my family faced catastrophic health issues, my maximum out of pockets is less that 15% of my income. I am a reasonably high earner, though nowhere near the 1%. Lower income Americans have extremely generous subsidies on health insurance and medical providers often have programs to reduce or completely write off medical expenses of people who can not afford them.

> I am not sure what holds the US back to have a humane care system.

A huge industry (almost 18% of US GDP) that has a lot of lobbying power and influence, combined with with decades of anti-socialism messaging.

>I am not sure ...//

It's simple greed, people want to be healthy, rich people can interject themselves into that desire and 'tax' health/wellness.

Yay capitalism!

Please don't take HN threads further into ideological flamewar.


That’s probably over simplistic. The current US system doesn’t actually benefit most well-off people; the person who wrote the article probably qualifies as rich by most metrics. There are obviously companies which benefit, but on the whole it’s like it is because large-scale change is hard. Note that even the modest reforms under Obamacare were politically poisonous at the time, even though its somewhat popular now; making a change with long term benefits but short term cost and inconvenience is always hard politically.

I think many Europeans don’t really understand how much less centralized and cohesive the US is than any given European country. That plays a big role in why our system of health care is so disjointed.

I made this mistake last year, choosing a start date of the 1st. Normally, this would not have been an issue, but it took my employer several weeks to have their benefit management company activate my benefits.

Fortunately, my act of loudly demanding they make the benefits retroactive to the 1st got things sorted very quickly. But, this is because I knew how things worked.

I would also recommend to US-persons to not switch jobs around a month boundary.

The employer-linked healthcare system is burdensome to both employers and employees. It’s not going to change without a dramatic change to the group insurance model.

COBRA is the name of the program that covers time between employment.

It sounds insane because it's not truly how it works in the USA. This author was probably unaware of COBRA.

When you quit your job that offers healthcare benefits, you can temporarily continue coverage under COBRA. This is a required program for any employer with more than 20 employees:


Essentially, if something happens where you need healthcare services, you have your previous insurance billed and retroactively fill out some COBRA forms and pay your premium (which will be higher because your employer isn't contributing anymore, but the price is capped to 102% of the overall cost).

If you don't end up needing any healthcare services, your previous employer's plan just ends automatically.

Also, a loss of coverage (i.e. by job loss) is a qualifying life event for a coverage change. This author could have enrolled in an insurance marketplace ("Obamacare") plan immediately, although the alternative of using COBRA for a small employment gap is usually preferable.


It's fundamentally flawed, no questions there. But usually you are covered under something called cobra I think.

You may optionally purchase coverage under COBRA, typically at the full price, which your employer is required to sell you (assuming the employer meets certain criteria).

Importantly, you can purchase COBRA after the fact. When I left my last job I inquired about purchasing it because I’d have a gap of a few weeks. I was told by HR that the best thing to do was to hold off on purchasing it. If an event occurred during the gap, such as an ER visit or something similarly expensive, I could purchase COBRA and would have the expense covered.

There are also options to purchase backdated cobra if there is an emergency and you didn't purchase it initially.

I came to post the exact same comment. How can you build a functioning society with this type of BS? How can you encourage people to become entrepreneurs with this?

Many people will qualify for COBRA and simply don't realize that they have the option of keeping their insurance.

It's expensive, but that isn't a good excuse in this situation.

(it's been in place since Reagan...my point isn't really to defend the shitty system, it's to say, people should fully understand the options they do have)

This is why we have ObamaCare and COBRA.

That does help a consistently throwing patches over these issues make it harder and harder to make meaningful changes.

I'm convinced that the only way heslthcare will get better in the US is if a president sacrifices re-election and forces sweeping changes that hurt employment (insurance companies, employer-provided healthcare, etc.)

> Including paternity leave, I took months of paid time off. And when my father passed, my manager gave me all the time I needed to help my mother get her estate in order, and then gradually ease back into a work mindset.

Wow a month time off. Isn't that just normal?

“Months” not “month”

yup my bad.

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