Pros
Started as an amazing culture and company with Core Values and a breakneck pace that hungry career and growth minded employees thrived in. Benefits were robust, career paths attainable, and customer success stories delighted Slack channels. The HR team crushed hiring goals, recruiting and onboarding programs were industry leading. The annual CKO was inspiring, the commitment to contributing to the industry and community was exciting, and the friendships made were plenty (assuming you were not back channeled and on the target lists of the exec team - how dare folks speak up when leaders throw out sexual, racist, and drug laden epithets during meetings and offsites).
Cons
The land of the RIFs. DW was never able to truly build a product roadmap or GTM strategy. Executive after executive has been brought in, and exited, and all failed. Surely this should be a case study for an MBA class. Starting with the annual spend on swag and severance packages compared to product development.