Over on Q&A site Quora, several former Square employees have posted harsh descriptions of the working conditions at the booming mobile payments company founded and run by Jack Dorsey.One post concludes: “Many of the employees I know still there are simply waiting to vest, so that their time with the company holds some value. Many have left prior to vesting because it simply is that bad.”
The complaints centre on a few themes: high turnover, dictatorial management, and disorganization.
The posts have been up for a couple weeks now. At first, we declined to publish them because the fact is, working at all startups is hard and there are a lot of complainers at almost every company.
But in the intervening days, it’s become very clear to us that the posts are getting a lot of attention in the startup scene. A number of influential industry sources have reached out to us to ask questions like, “What the hell is going on at Square?”
So we decided to find out.
Square PR declined to comment, preferring to take the high road.
This did not stop us from digging, however. And now, a source close to Square has shared what sounds like a reasonable explanation.
That explanation: In the past couple years, Square has hired over 300 employees, multiplying its headcount. In some cases, the company realised it had hired the wrong kind of person and the relationship did not stick. In particular, Square management believes it may have made the mistake of hiring some people who were not ready for startup life. Some of these employees were described as “big company people.” Also over this period, about a dozen people left Square at the company’s request – “for cause.” It seems to this source that people in those two groups are the ones who are complaining about the company on Quora.
We buy it.
Working at startups is hard. The hours are long. Take-home pay can sometimes stink because so much of the compensation is equity-based. Because startups are doing something new and unproven, their future is uncertain and this can be stressful for people with lower risk tolerance. Because startups have to sometimes change priorities in a moment, projects are invested in and then abandoned.
Finally, working for a founding CEO isn’t always pleasant. There is a reason for this. The act of creating a new company takes an incredible amount of passion and energy. The kinds of people who have that much passion and energy – visionary types with the ability to execute – tend to be a little pushy.
Can you imagine what the Quora threads about working at Apple would have been like if the site had been around back in the early 1980s when Steve Jobs was a humongous jerk to work for? He made people cry … all the time. He shouted and threw things. Bill Gates was also petulant. Mark Zuckerberg had no problem being ruthless with his cofounders and early executives.
Think about all that as you peruse the following answers to the question “Is Square an unpleasant place to work?”
Here is the most “up-voted” answer from an anonymous contributor:
As a past employee of Square, I will say it was the best place I ever worked, then slowly became the worst.
The culture is absolutely one of brainwashing with transparency constantly being touted as a tenet, but rarely executed. Most questions that are asked during weekly Town Square meetings have thought-out answers that perfectly fail to address the issues raised. Jack is great at speaking in a compelling way that makes everyone forget what the original question was in the first place.
Employees are rarely given praise and constantly criticised for any small error. I agree with the post that states employees are constantly reminded of how lucky they are to work for Square, as if they have no qualifications or skills of value. This creates a sense of fear and one that makes employees scared to even bring up issues.
Ego is another problem as some employees think so highly of themselves, they often forget that they have actual work to get done to be successful.
The HR process was so shoddy at times it was downright illegal. There is no accountability for management and most have little or no experience with people management leading to employee resentment and surprise-poor management of individuals. This in turn, leads to unhappy teams and due to ego or fear of their own positions, those managers usually target whoever raises issues with their leadership (or lack thereof).
Basically, you have to keep your head down and take whatever is thrown at you. It really is sad because I truly believe in Square as a product as do the majority of the employees, but Square has lost a significant portion of their talent because they have failed to address these issues.
Many of the employees I know still there are simply waiting to vest, so that their time with the company holds some value. Many have left prior to vesting because it simply is that bad.
My goal in responding to this question was to add my own experience as a past employee and convey the feelings and thoughts of many who express similar experiences at the company. I truly hope that Square addresses these issues and instead of denying the claims or attempting to scapegoat whoever has posted on any of these threads, commits to effective solutions through engaged discussion with the entire company. As I have constantly stated, I love Square. It was hard for me to make the decision to leave mostly because I believe in the product and the potential it has to change the world, but ultimately I had to be happy doing the work I was doing and under those conditions I was not. My biggest concern has always been that Square acquires some of the most talented people, mismanages them and then ends up losing them
Here is a concurring response from another anonymous Quora user:
I was about to write a long post detailing my experiences as well but I think Anon User a couple posts above summed it up quite nicely. Link to post in question:Anon User’s answer I’ll add my thoughts in any case.
I worked there for about a year and a half and the honeymoon got sour after it started to expand at a ridiculous rate (about 175 new people started in my time there). It had some of the worst growing pains and a nasty habit of hiring inexperienced management. Sadly that continues to this day. As of late, they had someone with barely a few months of management experience heading up management training programs. Yeah.
There is most certainly a circle jerk kind of culture there. They’ll convince you you’re the luckiest person in the world to be working for an amazing company. For the most part, they are an amazing company, at least when it comes to product design and user experience. Their design skills are top-notch and they’re probably the best product in its class. I still use the product occasionally so I certainly don’t have any ill will towards the end result. Just the environment they decided to build for the employees.
The work culture is beyond your standard “work long hours startup”, Square wants your soul. After voicing my concerns to my manager that the amount I was expected to work was jeopardizing my overall happiness and time spent with my spouse, I was told in no uncertain terms that I could either choose to spend more time on my relationship or Square. There was no middle ground. As you can probably guess, I chose the former. I expect that relationship to last much much longer than Square will be around for.
Jack is a curious CEO, though with little experience running a company. I mean, the guy got kicked out of Twitter. He also works two full time jobs, both as CEO of Square and whatever he does at Twitter nowadays. The company culture comes from top down. When your CEO works two full time jobs, lives within a 4 block radius of both of them, doesn’t invest a lot of time in friends, family, or other non-work related relationships, everyone that gets hired below that is expected to do the same. My own social life started to dwindle rapidly in my time there and almost everyone else I spoke to experienced the same. Soon, the only people you would hang out with would be the people you worked with.
They have an “unlimited vacation policy” but it is seldom taken advantage of. What use is an unlimited vacation policy if you’re guilted into not taking any at all when you’re already working late hours and often weekends? Even if you were visiting family during the holidays, you were expected to work through that. Not just on call if something was broken, but the same kind of work you would do any other time. It’s not like the company was so small there was only one person that could do a specific job, it had definitely grown to the point where everything would be totally fine if someone took a week off. But few did. And those who were lucky enough to do so were met with a very disappointing attitude about it.
Square is a perfect environment for the fresh out of college graduate that has had everything taken care of for them their entire life. They’ll give you 3 meals a day and since the only thing you do outside of work is sleep, you can afford an expensive apartment close by, even if their pay isn’t quite up to par.
If you don’t fit into that or a similar category, good luck! Perhaps you should look elsewhere since this isn’t the right place for you.
Here is a counter-point to the above answers, a more balanced answer from Louie Mantia, a former Square designer:
My hiring process is somewhat unique and calls for a different kind of introduction. I simply contacted other designers at Square to see if they would be interested in working together. I met up a few times in the evenings with them and soon enough I was hired as a visual designer (for what was Card Case).
Square has awesome problems to solve. Very complex, tough problems. It’s quite appetizing to go and work for them, and the way they portray themselves externally definitely looks great.
And it was great. It was a lot of fun working with the people at Square, and there are some really talented individuals. Having worked at Apple in the iTunes organisation for a year and a half, I can say that things are quite different from how a larger company like Apple operates. Square is very much a startup and behaves as one, which has both pros and cons.
Square provides food, beverage, and snack options throughout the day and into the evening, which make it easier for you to stick around and work more at the office. There’s a pool table and a bunch of couches and nice chairs to sink into and get things like email tackled (which, by the way, there’s a lot). It depends on what kind of pace you’re looking to live and how much time you need to devote to outside-of-work activities like friends, family, and hobbies.
Square is solving almost the same problems again and again, in slightly different ways. Designing the same thing over and over gets a tiring. There was enough for me to do, however, including fun things like artwork for Town Square (its weekly meeting) and movie tickets for company outings. It was more than just being a UI designer, it was being an artist at times.
At Square, there’s chances to influence products, though I would say that most of the work done is out of direction from others (like leadership). I became frustrated with Square when I realised that I was drawing things in an attempt to please management/leadership. I wasn’t trying to fix things as I thought they should be done. Instead, I was starting to design and think in Square’s mindset, not my own. And most times when I voiced my opinion, I was met with conflict. I was constantly prodded to “prove my work” by creating multiple versions of things (which I had done at Apple, but never to the extent I had to at Square).
I don’t know how other people work, but while I work, I try to decide what’s best and scrap other things. I don’t often keep things I don’t like.
And though I might have seemed stubborn, I believe that when you hire a creative person, you don’t hire them just for their ability to use a certain piece of software, but also for their opinions, thoughts, and guidance.
While at Square I worked on all three of their products: Pay With Square/Card Case, Square Register, and the NYC taxi project. I did rich visual design for every one, and sometimes the things I did shipped. I’m mostly proud of the work I did while at Square, but I’m disappointed with how my time seemed misused. I worked so hard at Square to accomplish very little.
When this became more and more true, I decided it was time to move on and create my own company in an effort to work for many different people, and it’s working out very well.
Ultimately, I do not think Square was right for me. It’s not to say that it wouldn’t be right for you, or someone else. But my overall experience was not pleasant, and not what I wanted in my career.
EDIT: I just wanted to add something else about what I look back on fondly. When I worked at Square, my happiest memories are times spent not working: company movie out at Metreon, Larry King visiting, and having great, casual conversations in cabanas with friends.
Contrast to when I was at Apple, my fondest memories were drawing app icons and interface elements. It sounds weird, but I really enjoy doing that (that’s why I made that my profession). And being able to do that for a company like Apple made me very happy, no matter how late into the evening I sometimes spent working on things.
I thought a lot about writing this and also thought about posting it with my real name, so I hope you can respect my honesty and openness. Please do not try to read too much into this or make any assumptions based on things I’ve said. My intention is to have been very honest in the hopes that it adequately answers the question.
Finally, here is a positive review from a current employee, engineer Zach Brock:
This is a challenging answer to write for a few reasons, so here come some caveats. I’m going to do my best to not sound defensive or like an apologist. I will try to give a nuanced, balanced and honest answer to a complex question. I admit that I wouldn’t have considered answering if some overwhelming negative answers weren’t posted first, but I’m going to try not to let those bias the way I answer. It’s really difficult to talk about startups (in particular hyper growth startups) to people who haven’t been a part of one, but I’ll try to be aware of that.
Ok, all that being said, let’s get started!
Obviously I can’t speak for everyone here, but I can talk about my experience and what I’ve observed. I love working at Square. I get to work with an amazing team of tremendously talented, incredibly smart and extremely nice people. We’re building a great set of products that people love to use and building a company from scratch that we want to work at. We’ve got a huge vision for how and why we want to change the world and we’re moving in that direction really quickly. On a more micro-scale, I love the problems I work on everyday, I like the rigour and discipline we apply to problems and I’ve made a lot of friends in my time here. The energy and enthusiasm in the office everyday is inspiring, the attention to detail and amount of thought that goes into everything we do is incredible and the speed we’re moving is exhilarating. I feel like I have a tremendous impact both on the people around me and on the rest of the world. I think the people I work with will all say the same things (and I encourage you to ask them!).
One of the things I’ve seen referenced a few times in other answers is work-life balance. In order to work at a startup, I think you need to be more intrinsically motivated than extrinsically motivated. This is why startups are often looking for Hacker-types. The kinds of people who spend all of their free time building something for the pure joy of it are a great fit for the startup lifestyle. These kinds of people put in a lot of time and effort into building things because they enjoy it, not because someone is telling or encouraging them to work harder or longer. If you personally bias more towards extrinsic motivation, you’ll probably find a startup difficult. There’s not a lot of formal motivation efforts or structure in place. You may interpret it as poor management or a lack of leadership. And that’s probably true for you, but not necessarily true for the people sitting next to you.
All that being said, working at a company going through hyper growth is a tremendously unusual experience both from a technical and an organizational perspective. Not only is your company changing tremendously, but the global context you’re operating in is changing as well. On the technical side, Jeff Dean of Google has a great rule of thumb for building scalable software systems: “Design for 10x growth, but plan to rewrite before 100x”. The kinds of problems you run into beyond 10x growth are so unknown to you right now that it’s not really worth considering them or investing significant time into designing against. Consider a hyper growth startup growing ~25-30% every month. That company needs to rewrite everything every 10 months. That would be difficult if you were just trying to maintain your current functionality, but you’re also trying to move as quickly as possible to iterate on your existing products and you might even be trying to launch new ones. It can be unpleasant to do this rewriting and re-architecting. But it’s worse to try and operate a system well beyond it’s limits. This tension leads to having to make a lot of tradeoffs on the fly and with imperfect information. This can be an disquieting experience for the kinds of people who prefer finding a global optima to a local one. The upside to all of this is that you get to work on a huge number of problems in a very short time frame. You get exposed to different technologies, business domains, product problems and scaling challenges. And as soon as you solve one you immediately move onto another one. It’s never boring.
I’m not aware of a corresponding rule to Jeff Dean’s for building organisations, but based on my experiences so far it’s probably something like “Design for 150% growth. Maybe. Good luck. You’ll need it.” People are a lot harder to design for and around than bits and bytes. As a company grows you’re going to see all kinds of weird growing pains throughout the organisation. Most will be natural and have few consequences, some will require explicit intervention to fix. Sometimes you end up with heterogeneous parts of the organisation and it takes a little while to reintegrate them into the rest of the culture again. We’ve grown incredibly fast, we’ve made a lot of mistakes, and we’re likely to make a lot more as we continue to grow. Sometimes making changes leads to unpleasantness; sometimes not changing things leads to unpleasantness. Often times the right solution is only obvious in retrospect. It’s a truism that at any given company, not everyone is going to be happy. It’s impossible to please everyone in an organisation of any size. I think Square’s biggest virtue as a company is our ability to identify problems, learn from them and correct them quickly. Rapid adaptability is the only guaranteed way (at least that I know of) to deal with hyper growth.
Working at a startup isn’t just about building a product, it’s also about building a company. As anyone who’s done it will tell you, building a product is hard. Building a company is also hard. Trying to do both at the same time is incredibly hard. Square is a great place to do both of these things, but it’s not always going to be easy and it might even occasionally be unpleasant for some of the people involved. What it is, without a doubt, is worth it.
 Evidence in favour of this: People who have started successful startups and no longer need to work often go on to do another startup. Not because of financial incentive but because they’re fundamentally motivated by solving hard problems.
 Surprisingly there’s no “Hyper Growth” topic on Quora yet.
 Some examples of change: launch of the iPhone, “Facebook” becoming a household word, the rise of AWS, the 2008 housing crisis, Kickstarter getting traction, the launch of Pretzel M&Ms.
 I used to sit next to Finance, now I’m across the office. I used to know every time Excel crashed, now I don’t.
 Support used to know everything we were launching by virtue of sitting next to all of engineering. Then they had no idea when things were changing. Now we have an internal mailing list for user visible updates.
 Google, for example, is consistently ranked as one of the best places to work for, but you can find a number of unhappy reviews about them on Glassdoor.
 Well, technically it’s impossible to please everyone given a reasonable expenditure of time and money, which puts startups starved for both at somewhat of a disadvantage.
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