Pros
The folks on the ground (read: IC's) at Handshake are great to work with. For the most part, there's a solid non-jerk quotient that is helpful for keeping one sane through all the chaos. However, I wonder if that sense of camaraderie is only there because of trauma bonding after the many negative realities of working at an organization like Handshake. From my experience, that trauma bonding and helping each other cope went a long way, but it definitely has a hard limit.
Cons
Handshake has had an unfortunate series of decisions from leadership that have resulted in a low quality product, low morale across the majority of teams, and a mistrust in leadership. The other ironic side of this is that there are many lower level leaders who have tried to turned the tide, and while they're heard at a surface level and solutions are agreed upon, those resolutions are later deprioritized. The rhetoric of what Handshake aspires to be and the realities of what their internal culture is day-to-day is in direct contradiction to how they've presented themselves. For starters, the leadership team has not learned how to aggressively prioritize. The majority of good ideas actually come bottom up from grassroots initiatives, but those are quickly deprioritized as well. There are so many product possibilities that leadership wants to try out that teams are absolutely pushed to the brink of what is sane to expect in terms of workload. This is not limited to engineering alone, and it feels like a company-wide norm. Hero culture is very much alive and well at this organization. There will be a high risk of burnout unless you're able to strongly hold your boundaries in place. Because of this lack of focus paired with a number of dismissals of a series of ICs and leaders, everyone is scared for their jobs. There is a sense that if you're not one of the favored people to leader or if you bring up actual problems to the organization, you're painting a target on your back for the next time that they need to cut back. At one point last year, the R&D organization moved towards what was painted as a "performance-driven" culture, but this performance was only to accelerate velocity. This shift resulted in low quality technical decision making, a cut-throat competitive nature internally, and a blameful culture around failures and incidents. Much of these symptoms feel like a direct result of decisions made by leaders that are subsequently poorly communicated. The mistrust of leadership runs high because of how poorly the past year or two has gone for the organization as a whole. There isn't a way to collaborate productively between leaders and teams.