Pros
Twilio is (was?) full of talented employees, who were creative thinkers, builders, and teammates. Unfortunately, the enthusiasm of many of these employees drained over the last year in light of faltering leadership (see cons). Work/life balance was fantastic, with remote work opportunities and unlimited PTO.
Cons
Management at all levels is a disaster. The leadership changes direction so regularly that it is difficult for teams to achieve their goals. Not only is this frustrating, but over time the cumulative impact of projects repeatedly being discarded is a huge hit to morale. Team and departmental management lacked the skills needed to motivate and grow their employees; in my 2 years at Twilio I was rarely provided with any practical leadership or professional development opportunities despite asking for them. Despite their stated commitment to diversity and inclusion, my experience was that men were regularly favored over women in terms of promotions, leadership opportunities, stretch assignments, and access to their skip-level managers. The majority of their stated anti-racist layoffs, at least on my team, consisted of women, people of color, and people with disabilities. It is my opinion that the DEI team that was established is just for optics; my team regularly interacted with them and they had a reputation for using intimidation and bullying tactics to achieve their goals - completely counteractive to how a DEI team should behave.