On July 20, 2020, about 6 months after I left the company, I wrote a review of Stack Overflow on Glassdoor. Glassdoor's model requires people to regularly submit information to their database in order to view contributions. This includes your own contributions. Since I wrote about the company's business, I decided to seek out my review and see if it held up. I don't feel like paying the contribution tax to see my own content in the future so I decided to save a copy. And where better than my own blog?

Cartoon castle with glass doors, digital art.

Of course that means it won't be anonymous anymore, but it wasn't all that anonymous in the first place. So here's my review of Stack Overflow from after I left the company.


This review isn't exactly going to be anonymous. I've written a bunch of blog posts to grapple with my time at Stack Overflow. When I was hired, I was so excited to be part of the company's mission. If you are reading this, there's a good chance you are excited too. And it really is a fantastic reason to apply. There just aren't a lot of places you can work where there's as large an opportunity to make a difference in the world as at Stack Exchange/Overflow. I have criticisms of how the company does remote work, but they have years of experience and do it better than most.

I don't have any insight into other parts of the company, but Stack Overflow has their choice of engineering talent. It's hard to imagine I'll ever work with a better group of people. Not only are they skilled, but everyone I worked with is personable and interesting.

Stack Overflow is the sort of job that will enhance almost everyone's resume. Everyone involved in programming and computer technology will recognize the company and be curious about what you've done. It's an opportunity that's difficult to pass up.


You should expect a pay cut. Since the company has no problem attracting talent, they don't have much incentive to pay for it. I've heard from many former coworkers (some who are alumni themselves and others who still work there) that they accepted a reduced salary in order to take the job. We were told the stock options and benefits made up the difference. Obviously options are not worth anything before the company has a liquidity event. The good news is a few years ago the policy was changed so that options can be re-characterized and retained when employees leave the company. The bad news is many people were fired or left before that time. It won't matter anyway if the company doesn't go public or get bought out before your options expire. Options are not compensation, but rather a lottery ticket with better than average odds of paying out an indeterminate amount.

Benefits might be generous for your circumstance, but I found my company before and my company after Stack Overflow offered similarly valuable benefits. Before you assume free medical will be a win, pull out a spreadsheet and compare each item and how much it's worth to you. I can say the sabbatical I took ended up being a difference maker for me, but you have to stick with the company for 5 years to get it. Before you accept an offer, do the math and negotiate for yourself. (This isn't unique to Stack Overflow, of course.)

If you get into the interview process, make an effort to get to know as much as you can about the people in your reporting structure. The two things you need to be watchful for are: 1) managers who are out of their depth and 2) managers who don't understand the product. I was fortunate enough to work under people who met those criteria, but due to reorganizations and other changes, I lost that protection. The job went from a real joy to misery within months. All it takes is one weak link in the hierarchical chain for things to fall apart.

Like many companies, Stack Overflow has a feudal management structure. People are awarded and punished based on personal allegiance. Effective management protects the underclass from court politics while using influence to retain resources. Management sold itself under the banners of "servant leadership" and "pluralism", but these ideas were not used in practice. I think some managers believe in these (very noble) principles, but it takes only a few people to disrupt the balance. With no other management structure in place, people naturally tend to help out the people they know best.

I only have rumors to go by, but it seems the free lunch at the office came with a cost. Be extra cautious about moving to New York, London or Munich in order to take a position. Obviously if you want to move for other reasons, this is a good chance. Go for it! But office politics sounded way worse in the office than at home. If nothing else, it was useful to close the laptop and spend time with family at any point in the workday. And then there is more unsavory gossip which you can read right here in other reviews.

All that falls to insignificance compared to the main reason to avoid Stack Overflow: management has discovered a way to spin gold into straw. I don't just mean their monetization strategies, but also the way they waste the talent given them. It manifests in so many ways:

  • People toiling on projects that are doomed from the start.
  • Shifting priorities that keep people from doing excellent work.
  • Broken promises.
  • Naked disdain of business ethics.
  • Lack of executive sponsorship for follow though.
  • Reinforcement of short-term thinking and punishment of good strategic choices.
  • Hubris.
  • Doubling down on mistakes.

It's not hard to find examples of this, but one that stands out is The Loop. As far as I can tell, this was a pet project of the new CEO. It was not a bad idea in conception, but had a tight deadline that seemed artificially set. A number of experts in various disciplines gave feedback, but because of the deadline pressure, much of it was ignored. The result was a flawed survey. Not only did it publicly display embarrassing oversights, the data collected was largely useless.

Even for people who are allowed to succeed at their specialty, organizational dysfunction can be discouraging. Watching opportunities go untaken and talent go fallow isn't pleasant even if your own career is growing. If this were an uninspired job in banking, government contracting or something, it might not be so hard to stomach as at a company posed to make a meaningful difference.

Advice to Management

Demonstrate truth and reconciliation. It looks like you are trying to run out the clock before someone will buy the company and I don't think you are going to make it. The baggage of poor management is slowing you down and the only way to ditch it is to be open about your mistakes and ask for forgiveness. Listen to people who aren't in your normal social sphere. Go through the last few years of exit interviews and fix the problems one at a time. Stop shifting blame.

There are some out-of-date items in the review. A big one is that the options turned out to be winning lottery tickets. An awful lot of people, especially long-tenured engineers, packed their bags and moved on to the next thing. I was fortunate enough to get a payout sufficient to start construction on an ADU. So I guess I was wrong about that part; management successfully ran out the clock.

I don't know how much of the praise I heaped on the engineering team holds. A lot of good people left when their options paid out and I gather engineering got the brunt of the most recent layoffs. There are a handful of people still around who I'd love to work with again. The Community Team is quite strong even after the layoffs. As usual they are quietly holding everything together on the sites.

I can't imagine the benefits are anything like they were when I left. One cost savings of company mergers comes from consolidating benefits and HR. Update: I have it on good authority that this basic system is still used, but has been improved. I'll explain what changed after describing the system as it was when I joined.

For the record, free medical coverage was structured in a clever way:

  1. High deductible insurance to minimize the premium Stack Overflow paid.
  2. Employees pay for health care our of pocket up to the deductible.
  3. Employees submit their expenses to be covered by Stack Overflow's health reimbursement account (HRA).

The clever bit is that HRAs get special treatment in the US tax code:

Employer contributions to an HRA are excluded from an employee’s gross income and wages (hence are not subject to income or payroll taxes). Distributions from such arrangements for qualified medical expenses are tax-free.

It works especially well with a younger workforce that might not have medical expenses other than preventive care which is covered in any case. Most employees will only spend a little, so it's cheaper to us an HRA than pay the premium for a lower deductible.

Why don't other companies use this scheme? Because it shifts a lot of the burden of medical billing from the insurance company to the employees. After paying medical expenses, you gotta hunt down the Explanation of Benefits (EOB) and submit it to the company managing your HRA (usually a third-party contractor). If you don't submit your forms correctly there's a good chance your claim will be rejected and you'll be stuck with the expense. Fortunately I was able to sort these things out, but it wasn't stress free.

Further update: I was reminded that the system was changed so that the insurance company also runs the HRA. As a result, employees don't need to pay upfront and get reimbursed. Instead, they tell providers to bill their insurance who pays out from the HRA until the deducible is reached and they pay out of insurance coverage. It occurs to me the change was made before I left, but we'd pretty much gone to my wife's insurance (Kaiser, which is a wonderful HMO) by that point. Or at least that's my excuse for not remembering this.

I mentioned The Loop. The most recent post was Fall of 2021, so it lasted 2 years. I don't know how much data they ended up getting from the survey I mentioned. The CEO does post on the blog every quarter. Unsurprisingly, he gave up posting on Meta. While I don't really expect the CEO to be involved with the community, he had committed "to continue posting on meta at least quarterly." He seems to be listening to his peers (Silicon Valley CEOs) rather than his potential customers. Hard to argue with $1.8 billion, though.

Overall, I stand by this review. If Stack Overflow is hiring and you want to apply, be on the lookout for teams that have strong executive sponsorship and ethical leadership. Opt for remote work unless the office is really important to you. Don't settle for a pay cut and compare benefits carefully.