Pros
The individual contributors are super talented, collaborative, and genuinely care about doing great work, they're honestly the backbone of the Design org right now, driving both the culture and the success. The benefits at Toast are solid, although they keep pulling them back. And the company itself is working on some interesting stuff in the restaurant space. Remote work and work-life balance are definitely the biggest perks, but even those can be tough to hold onto with constantly shifting priorities and a lot of unnecessary work piling up.
Cons
The Design org is in disarray, and the blame lies squarely with leadership. The Chief Design Officer has made a series of misguided, top-down decisions that show a clear lack of fundamental understanding of design, research, or team dynamics. There is no strategic direction, no clarity, and no investment in the people doing the actual work. The culture and camaraderie that once made the Design org great has dramatically diminished in the last 2.5 years. Growth and actual people management are nonexistent. Managers are expected to focus on constantly changing strategy, leaving little time to actually develop and grow their reports. Senior leadership is judgmental in the worst way, and has no interest in ICs, they meet in person often and truly nothing ever comes of it other than a feeling of divide. Talented designers are left to flounder without guidance or support, while leadership avoids hard conversations and pretends everything is fine. Morale has plummeted...and it’s not subtle, the ROR results showed it clearly and it just continues to decline. Cutting research made this worse, nothing like losing some of the best talent and people on the team - only to be told they'll be replaced with others - to create a feeling of insecurity and apathy. The discontent across the team is loud and visible, but somehow design leadership faces zero consequences for the damage they’ve done or lack of impact they have had. Cutting research was, without exaggeration, one of the worst decisions the org could have made. It reflects a total disregard for user-centered design and a fundamental misunderstanding of what drives product quality and business value. "Anyone can do research" and a focus on Quant is not what makes a successful product or design team. Stop blindly following what the FAANG companies do and think for yourselves and what works for the Toast org. That decision alone signaled to many that leadership doesn’t respect or understand the very discipline they’re supposed to champion. This is not just a team with growing pains, this is a team being actively mismanaged by people unqualified to lead it. Until there is a complete overhaul in leadership or serious accountability, the decline will only continue.
