Vantaggi
Management is very, very good, along basically every axis, including technical skill. Company is very friendly, coworkers are very talented and nice. People are very straightforward and easy to work with. Most inclusive management I personally have ever experienced in my career, not in a fake overly supportive way for PR, nor in the sense which I feel the tech industry often uses the word "meritocracy", which I feel is often code for "don't rock the boat". I felt very lucky as a gender minority to have started my career here. In tech I have generally accepted a certain level of background radiation discrimination, but I really have not found it at Obsidian. Obsidian always made it easy to focus on my work, with managers that were interested in results, not micromanagement. I found management open to feedback, particularly about tech. As a bonus, I felt the company was good at working with the complexity and internal politics of any type of client, so everything always felt very collaborative. I never felt the adversarial environment that a lot of tech can have. I found that Obsidian tends to have very cool clients to work for, both in terms of technology and scope. My coworkers were and are all extremely intelligent and skilled and very good resources to learn from, I can't speak of them highly enough. With the state of the tech industry, this almost feels silly to talk about as an employment perk, but their tech really is state of the art, and constantly improving. They invest in homegrown tech and also adoption of new tech. I've known people who took paycuts to work at Obsidian because of the tech (among other things). Their website, as of time of review, says that their tech is their secret weapon; this is true, not that it's their only competitive advantage. I chose to spend all my time working on Haskell, and while it was fun and educational, in retrospect I think I should've taken them up on their offer to rotate around more, to stack my resume a bit more. Company is all remote now and good about working remote, I think they have pretty good processes around it. When I first joined they had some people remote, but also an office in NYC, which I don't think they're using anymore. Company is VERY flat. I think this is a good thing, but if you're early career, I would advise: keep track of your time, stay organized, and most importantly, be active and not passive. I really appreciate that Obsidian took a chance on me when I was an underrepresented and early-career talent. I think it was probably the place I got by far the most career/talent growth. Obsidian taught me so much that within just a few years after leaving I had started my own startup. I liked Obsidian so much that when that startup ended, I came back to Obsidian. Take that for what you will. Since coming back, I've found that it's even better than when I left, and now their central thesis of investing in tooling and talent is paying off. Due to the excellent tooling and the excellent staff, I think you will find that it is quite easy to succeed and be productive, and that the primary ingredient is stuff like motivation, organization, effort, focus. At time of writing Obsidian is growing quite fast.
Svantaggi
None of these are true general cons, and most of them are things I personally like, but are things I think one might want to keep in mind. Most of it revolves around the autonomy that management gives you, which I would say is a benefit, but can be a matter of preference. This section is longer only because it requires more evaluation than the pros, which is all stuff I believe is generally unconditionally positive. Also, keep in mind: I am not a lawyer, none of this review in any segment is legal advice, any segment about contracts is just what I observed, either during my time at Obsidian a few years back, or my time since rejoining, and obviously I am biased as someone who is currently very happy with my employer. To compare the wages for a small consulting firm with FAANG would be a category error. It's very good money on an absolute scale, and at least for myself as a W2 employee a few years ago, I did actually get automatic raises for inflation. Management made it possible and easy for me to succeed, but obviously the company is only so big, with so much ability to absorb risk. When there was a downturn during the market right after COVID, I was the least experienced, so I was selected part of layoffs during the start of COVID. They actually did actually rehire me and others. In retrospect, I think it was quite fair. But it's worth noting. Their job listings on their site have no paid vacation you are mandated to take (US W2 listing had a baseline of 2 weeks PTO). I didn't perceive any up-or-out, nor did I get the vibe of lifetime employment/untouchable tenure. Obsidian seems quite keen to have you learn a lot and gain a diverse set of skills, they recommend me at least partially rotating projects, but again, they only give you the choice, and I turned it down. I regret not taking further advantage of it, but I still am glad they gave me the choice. I think you have unlimited upside possibility here, so my advice is to be your own advocate, and be more ambitious than you thought was possible! Obsidian is a successful for-profit business. I was never told any false pretenses about being "like a family". Personally, I really appreciated the honesty. This isn't me downplaying some type of grind environment: I've worked some other jobs that pretended to be anything other than a for-profit company, and at times they felt like playing Death Note mind-games where I was pressured out of social obligation. Keep in mind also that the founders are skilled lawyers (per LinkedIn). I'm now working internationally and my contract included a term for US choice of law, so my more favorable local law has limited application. Thankfully, in my personal experience, they seemed to really use their skills to avoid taking on legal risk, not enabling illegal behavior. The company is growing like absolutely crazy right now so you have to stay doubly on-your-toes to get a hold of management: if management is too busy they will tell you to keep working your way down until you find the person that still has time.