Squarespace

• Profitable, stable, public company
• Equity that is worth cash and not monopoly money
• Lots of unsolved problems and room for impact, unlike FAANG, where not all problems have been solved!

• Leadership from directors up to the C-Suite. At the lower levels are newer leaders who are more focused on building armies than solving problems. At the higher levels, just dispassionate and tired.
• Technical debt. This is a 10+ year old codebase that has gone through multiple major framework changes, monolith to microservices, etc. It is showing its age and is hard to move fast with.
• Politics. The company can feel very siloed and lacking collaboration across teams and orgs than most of this size.

Stop focusing on superficial things, like design-first companies, Super Bowl ads, and vanity metrics, and start focusing on things that matter, such as customer satisfaction, ease of use, uptime, and reliability.