Pros
The engineering teams are great. There are a ton of knowledgable folks and they are very easy to work with. Great cross-team collaboration including with designers and PMs. The ease of working in the stack has increased in the time I was there. Generally speaking, the engineering leadership knows where it wants to be and is in the process of trying to get there. They appear to be very well locked in on goals. I have seen folks move up and take on new responsibilities and titles. There's definitely room for upward and lateral movement. I directly saw folks change teams to work on projects that were more interesting to them. Engineering managers would rather have a person stay in the company elsewhere than leave. DEI: One thing that I thought was great was the ERGs (Employee Resource Groups); they were phenomenal. They were a wonderful resource for folks in underrepresented communities and had a lot of buy-in around the company. I don't know all the details but they had some budget for events. One thing that I think deserves to be mentioned is that the goal of making small businesses more profitable feels very noble. We know that they are very important to our economy and it feels good to build tools that empower folks to take their businesses to the next level.
Cons
After two rounds of layoffs in 9 months, it remains an open question of whether or not it will be possible to actually achieve those goals. After the first round of layoffs, the leadeship team rightly tried to take some responsibility and present a clearer picture of where the company was. I would have said they did a decent job until the second round of layoffs came unexpectedly. It is impossible to believe that you can paint a rosy picture of the outlook of the business and then need to resort to a second round of layoffs. You were either dishonest about the outlook, or you are callously cutting. Neither is a good look especially after the belt tightening of the first round of layoffs. Executive leadership talks a big game but is clearly all about chasing that money. They're actually decently up front about their ambitions but they have REALLY drank their own koolaid. It's kind of creepy but at least they're upfront about it. Even before the second layoffs after the first there seemed to be a trend of long-tenured employees leaving the company. I can't say they knew anything but it was enough that it was a real trend that was noticed and discussed. Many left for really good reasons, but it was still alarming. While the ERG's were good, I never could tell how committed to them the exec team was. To their credit they did try to listen but I honestly don't know much they "got it." During an onsite trip the Women in Tech talk was chaired by... the two dudes in the C suite. Many were not impressed. Overall I think if the company can get thru the next year which promises to be very rough their long-term outlook seems good. The days ahead will probably be crucial (and not very pleasant) for them though and decide if they can actually become the company that the founders see thru their rose-colored glasses, or whether they let the pursuit of the hustle culture grind them into ashes. Good luck to everyone left.