My Terrible Experience Applying for a Job at Crossover for Work by@davidsiegel

My Terrible Experience Applying for a Job at Crossover for Work

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David Siegel

Start companies. Think thoughts. Write books. Give speeches. Save world.

Andy: “Okay people, we need to hire some new talent for a big client. I’m going to need someone who can get at least 40 questions right on a 50-question multiple-choice test in 15 minutes. Probably have to guess some of the answers because of the time constraint. Do we have someone who can do that?”

Right Hand Man: “Absolutely. Rob has all the test-prep files. I’ll ask him to start memorizing.”

Andy: “Great. Now I need someone who got good grades in school and can write 50 high-performing topic sentences in a Google spreadsheet.”

Right Hand Man: “I think Gabrielle would be good for that. I’ll ping her on Skype.

Andy: “Fantastic. We need to write a dozen job descriptions. Who knows the format?”

Suneel: “I do. I’ve written a few thousand of them. I have the Excel template. I always hit the word-count on the nose.”

Andy: “Perfect. Now, the client wants to know: six is 12 percent of what number?”

Sandra: “Fifty.”

Andy: “Very good, Sandra. How did you know that?”

Sandra: “You asked it in the last meeting.”

Andy: “Good attentiveness and retention. Now, we’re going to have to evaluate and rank about 500 candidates. Do we have the right keyword-recognition software?”

Danielle: “I just fed in the latest keywords and it’s ready to go, Andy.”

Andy: “Who is good at comparison questions, like “Proficient is to practice as …”

Everyone: “Strong is to Exercise.”

Andy: “Right, I always forget that one. Can you take those, Esmerelda?

Esmerelda: “I’m on it like brown on rice, Andy.”

The meeting goes on like this for another half hour, because this is what we need in businesses today — people who can follow instructions exactly.

The Bait

Crossover for Work advertises dozens of jobs all the time, many of them highly paid, many for senior developers and architects. Everyone works from home. They have extensive software systems for tracking employee performance.

Because they pay so well, they get thousands of applicants. Because they get thousands of applicants, they use standardized tests and automated screening exercises to eliminate most of them.

I was interested in a job they had advertised — being CEO of an acquired company. This involves using their template and system to run the company, of course. They say this job pays $800,000 per year, so I decided to apply.

I have worked for myself for 40 years and have been CEO of a dozen startups. I don’t have an MBA — a universal signal of business competence (except for the fact that only 14 percent of billionaires in the world have one). But I was once a candidate to be the dean of Stanford business school, so I figured I would have a shot.

First, I had to take an initial CCAT test, which gives you 15 minutes to answer 50 multiple-choice questions. The questions involve calculations, comparing shape differences, analogies, word definitions, word problems, etc. They tell you to practice using the JobFlare app, which gives you completely different questions and has nothing to do with the CCAT.

This is the kind of test it would be easy to do very well on with unlimited time, but in 15 minutes you have 18 seconds per question, making it impossible to get them all right. There’s no penalty for guessing, so you do what you can and guess the rest. There’s no chance to go back after you answer a question.

I have studied statistics, behavioral economics, and decision science. I figured I would do well enough to get through this part of the screen.

I didn’t. It wasn’t even close. They want you to get 40 or so right. If you don’t pass, you have to wait 6 months to try again.

I waited. I still didn’t have work, so I tried again.

I realized this is similar to an SAT or GRE test. To win, you must game the system.

Crossover CCAT

So I went to and paid $50 for their study package. This was an incredibly lame product. It was a very basic page of HTML with some links. Two links gave me a chance to take a real CCAT test without getting my score (that probably costs more). Then, there were five PDFs containing test questions like a real test. It wasn’t a test app, it was just PDFs. You get the question, then the answer. You have to scroll a lot. Some answers have explanations, some don’t. A few of the answers are wrong. Several of the tests have repeat questions. Then there was another test in a different format.

I wrote to Mark M ([email protected]) and told him I was very disappointed that he would charge $50 for such a poor product. He replied:

Hi David,

A lot of effort was put into producing the .PDFs with the answers, that is the main study material. Everything you received was listed before you purchased it. Why exactly do you deserve a refund after receiving all of the study materials?

I said thought it was a very poor product that made the customer do unnecessary work. I asked him for a partial refund. He replied:

Out of the hundreds of people the made good use of our product, you are the only one that complained. Thanks for being an ungrateful ass.

That’s customer service!

So I suffered through the PDFs and memorized a bunch of the questions. Probably about 15 hours of study. I can’t recommend his tests, but you do need practice tests to pass.

Taking the Test Again

I felt I was ready, so I took the CCAT test again. Fortunately, many of the questions were exactly those I had memorized from the practice test, so even though it was really presented poorly, the test prep helped a lot. I knew the answers and could move on and spend time on the new ones.

I must have come very close, because the system said I had almost passed and would be allowed to try again. I tried again the next day and passed. It wasn’t easy, but because I had memorized so many answers, I was able to finish early and still pass.

The Essays

Since this is a job where you are running a company, they want to see if you have the skills. So they ask you to pitch a business idea in their format. They want an outline, then they want a narrative that anticipates and handles objections. They give instructions and use Elon Musk’s pitch for Tesla as a key example. Then, they want a 5-minute pitch video.

Since I know venture capital well, I created a pitch around a next-generation venture product that is very innovative. I spent about 15 hours on these documents and making a five-minute video. I sent them in.

Here is their response:

Thank you for taking the time to apply to Crossover.

We’re sorry to inform you that we can’t approve your application at this time — this means you will not be considered for this position.

That’s it. Thirty hours of work, $50 on test-prep, and that’s what I got back.

The Switch

Do they really pay as much as they advertise? I expect they don’t. I expect no one actually qualifies for the $800k salary for CEO of an acquired company — it just gets a lot of people to apply via their automated system. I would be interested to learn how many of their $200k-and-up jobs actually fill at that salary level.

The Reviews

On, there are over 850 reviews of Crossover for Work. The vast majority of them are negative. They say things like:

This company thrives on dysfunction, disorganization, and fear. You are constantly walking on eggshells, constantly having to fight for accurate payment for work you’ve already done, and constantly having to take a stand to receive the most basic things.

Pros: None that I know of. Even pay is bad. Cons: Very bad organisational culture.

I worked at Crossover for Work full-time for more than 10 years. This company uses people as tools, plain and simple. If you work in the US, and want a real competitive wage, and the ability to think creatively, be rewarded and recognized for your contributions, feel like a real contributor and want other typical things — like health care, 401k, health club discounts … well, this isn’t the place for you. Worksmart —their monitoring tool — if you are a professional, especially an engineer who often has to think creatively to solve problems, you don’t need a “key counter” or screenshots — or even a CLOCK to punch. You need time to focus without worrying if you’ll be paid correctly, not whether or not their algorithm detected you weren’t so productive for 2 hours on Tuesday. Please, use your talents at a company that cares about its products AND its people.

They are taking screenshot of your screen every 10 minutes. You can be fired with no reason.

… despite being the highest performer on my team I was let go because the bottom line is others on my team were just liked better by my manager. I don’t have any tolerance for those games, that’s why I liked crossover, because the metrics couldn’t lie. But people still can.

There is a bleak general atmosphere. I haven’t met anyone who is putting in more work than it’s required of them. Everyone is doing their job just enough to not get fired, which suggests a lack of passion, and it’s due to the way employees are viewed by management. The arrangement is such that anyone can be let go at the drop of a hat, which makes it all the more difficult to reach a state of mental comfort conducive of focus and performance. There is no actual motivating factor other than that weekly paycheck.

It’s very dehumanizing to define a person by the sum of their metrics.

Basically top management is obsessed with that stupid idea of creating a factory producing/maintaining software products on assembly line and they seem to be ready to sacrifice everything for that ideology. Nobody cares about real result, the only things that matter are metrics and FTAR (first-time acceptance rate). The latter basically means that you’ll be screwed up for any minor mistake like failed code review or some mistake in jira ticket.

There is no promotions or any way to show any recognition for a good work you are doing over there, you could be a top performer for couple of months and certain clients ask for your you to handle their issue and still you are in the same place, and to get a higher position you have to go through the tests as if you are an outsider.

What I really disliked: Constant tracking/ justification of work stream. Seriously. As others have pointed out, it’s difficult to actually *get* credit for a full work week without working extra. Especially in some of the higher-level, more ‘creative’ positions such as architect, product management, etc. there’s minimal or no opportunity to review or think over things. For me, I work in bursts followed by small distractions in which I’m running the problems in the background of my thoughts. A variety of coworkers and management in my history have almost universally commented about the volume of good work I produce. Even my peers at Crossover had no problem with the quantity or quality of my production. However, their tracking software and systems simply don’t credit anything other than linear, constant “work”. This was bad for me, resulting in me working extra, reworking things as I attempting to change my processes, “faking” it, or simply working longer to attempt to make my hours. I also felt bad for some of the more junior or “factory” positions. It really is tracked by the minute, with lots of incentive to find “problems” with productivity. This is really a thinly-veiled method of wringing blood out of a turnip, by finding flaws or gaps and essentially docking pay. Yeah, the salaries are good but the amount of ancillary work that goes into making “real” hours is awful, and I felt like a chump contributing to it. I had to quit for my sanity.

The reviews are worth reading. Some people like the work environment. Some people say they are pushed to be their best every day. But in my reading, it’s really the people who are good at moving things from the in-box to the out-box, not creative or critical thinkers. It didn’t surprise me that the best review was from a military guy.

Someone from Crossover responds to many of the Glassdoor reviews, though they are mostly cut-and-paste. Here’s a typical response:

We’re sorry to hear the experience didn’t work for you. It isn’t for everyone. The factory model is the best way for us to scale our business when acquiring one company per week. Thank you for the feedback!

Here’s a video from a guy who worked there for four weeks before finding a better job:

A good summary from an executive:

… the company likes to present itself as having a methodology that is fully repeatable and applicable to all of their businesses, but the reality is that this is only a (small) portion. It’s really that they have a bunch of talented people (and that’s for sure) held hostage by the wage/tracking situation who constantly over-perform until burnt out. I believe they could come up with a blended approach, that encourages performance without treating people like cattle (or gears) and maintains a high standard. Given the background of the founder, this is unlikely, as he’s long believed in this kind of philosophy. For me, it was a fun and interesting experiment that I am glad is over.

Why do People Work?

Management is hard. I always say that executives play golf because it’s so trivially easy compared to managing people. But management comes from a fundamental philosophy, and the fundamental philosophy at Crossover is that people are fungible work units that should be replaced by machines as soon as possible. They are a nuisance to be tolerated as long as they hit their numbers.

I wouldn’t fit in at Crossover. I’m not good with rigorous nonsense. I hire employees who ask good questions. I hire people who aren’t afraid to tell me I’m wrong. I want people who are willing to try something new, to fail, to learn. I want people who replace their own jobs with something better. I want people who will break the rules to make customers happy. I want to harness the intrinsic motivation in people to accelerate my company. I’d rather coach them and do experiments together than tell them what to do.

Like most people, I need income to survive. But I wouldn’t work for Andy Tryba for any amount of money. I’d rather work for Frederick Hertzberg:

or Dave Snowden:

or Paul Akers:

Or Jeff Bezos:

Or Ray Dalio:

Or Bob Sutton:

Or Richard Sheridan:

Or Leandro Hererro:

Or Gary Hamel:

I don’t think people work for money. I think they mostly work for a) enough money that they don’t have to worry, b) a decent, respectful, and challenging work environment with a chance to make their own decisions, learn, and improve, and c) to contribute to something they find meaningful.

That’s why I’m starting the Giordano Bruno Institute — because too many things in today’s society are broken, and they can’t be fixed by people who are very good at checking the box with the right answer when the other three are already known to be wrong. Because the world doesn’t work that way, and culture is critical to success.

Trying to control all the variables, including the people, is the illusion of control.

My Open Letter to Andy Tryba

I’ve paid $50 and 30 hours of my time to say this, because he wasn’t listening. Maybe he will now:


How long do good people last at your company? You can’t measure the opportunities you’re losing because you don’t trust your people and you don’t encourage innovation, creativity, opposing views, experimentation, and emergence. You’re building a monoculture farm, and we know monocultures can be wiped out by a single attack. A purely transactional culture is a graveyard for human flourishing. I am available to help you add joy and purpose to your company, but I’m expensive, and you’ll have to take a few tests. Here’s something I will teach you:

Satisfaction is to employees as profits are to growth.


David Siegel


David Siegel is a serial entrepreneur in Washington, DC. He is the founder of the Pillar Project. He is the author of The Token HandbookOpen Stanford, The Culture DeckClimate Curiousand The Nine Act Structure. He gives speeches to audiences around the world and online. He helps companies build a more antifragile culture and innovate faster. His full body of work is at

Also published at


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