Wealthsimple

As an employee it feels like leadership's solution to solving problems is often to just throw bodies at the situation. This is especially frustrating when it's an open secret that internally many processes can be improved or known to be flawed in some way, but employees aren't given the time to solve them properly, and eventually things boil over that require mass heroics on the part of employees to overcome.

Lots of internal corporate double speak / marketing speak from leadership. Some all-hands presentations really felt like the whole purpose was to indoctrinate people to the cause rather than to communicate relevant information within the company.

Constant and seemingly random re-orgs. Typical startup growing pain, but this coupled with the other 2 points really made it seem sometimes like there was a disconnect in where some of the real problems lay.

Very opaque career progression paths and salary bands as an individual contributor - literally impossible to get a straight answer from managers about what you should be working on to progress above intermediate. It seems that most managers themselves don't even know, and this leads to a huge disparity between "Intermediate engineer" within the company.

High variance in work life balance - some teams seem to be very relaxed while others seem to be worked to the bone.