Pros
The company hires some really amazing people who are a lot of fun to work with and learn together. I made so many friends at the company who I see on a regular basis outside of the workplace. Most people are very open and willing to help. The office is probably the best looking office any engineer will ever work at in the city or in the country. Benefits package is decent and engineers are actually able to utilize the unlimited vacation days. The company is very design first in terms of the aesthetics and it really shows in the product and everything Squarespace is involved in. It's a big draw for people who have a good eye towards design. There's a lot of flexibility to work on things outside of a team's ownership. Switching teams in engineering is doable as long as there are openings. For individuals with less experience, Squarespace has many people who are willing to be mentors and help provide guidance to those early in their careers. Many team leads and managers really make an effort to help new grads and interns.
Cons
Where do I even start.. * The CEO keeps a very small circle of trusted employees as leaders. Those in that circle get in by executing ideas as told and wield a lot of decision making power. The management structure is kept at a bare minimum and many executives and managers don't have enough time to devote to important issues outside of their core management areas. * Change is extremely slow - for a technology company, any ideas that come from individuals need to go through many layers of opaque and ambiguous approvals. * Many in management and executive team are not equipped or have desire to manage people. Some managers and directors are still doing individual contributor work such as creating user experience flows or code reviews instead of solving issues around resource constraints and hiring more people. * New product ideas and initiatives usually come from the top down and micro-managed from conception to release. Very few product decisions are validated by user or A/B testing. It feels like doing client work at a creative agency instead of a mature technology company at times. High priority cross functional projects are basically hell. * Retention rate is not great - People who have been around for a few years have the golden handcuffs and are waiting to cash out. The ones who joined more recently usually leave after a year or two for other companies that offer much better pay. Diversity and inclusion efforts feel disingenuous at times. * Compensation is not competitive - Squarespace's initial offer is always a step below what other New York companies in terms of total compensation. If cash bonus and stock are taken into account, the companies we compete with for talent usually pay 30-50% more for experienced positions. Annual raises barely keep up with inflation and stock refreshers are abysmal. * Promotions are hard to come by - Team leads at Squarespace are essentially managers at most other companies but have no power to determine promotions or compensation here. They are also not equipped to have conversations about what it takes for an individual to advance to the next level. Someone much higher up makes promotions and compensation adjustments for employees who they may not know. * The cultural values we used to have are slowly dying. Instead of doing a good technical job implementing product features and releasing products when ready, there's been a rush to deliver quickly at the expense of cutting corners and creating more tech debt. People are so busy with their own deadlines that they don't have time to help others anymore.