Squarespace

Great business, sustainable customers and revenues

• Great office location and view, with rooftop and beers
• Modern tech stacks with a lot of interesting technical projects going on in both Infrastructure org and Product engineering org
• Flexible working policy (WFH, leave early or come in late)
• Unlimited vacations (4 weeks are considered normal)
• Newly established career ladder (it's not perfect but better than nothing)
• Growing business with new products lines
• Likely-minded co-workers

Disclaimer: all the cons mentioned below can only speak to my own experience and serve only as subjective information for potential candidates interested in Squarespace.

• Poor immigration service with limited bandwidth and slow progress; as a non-US foreign worker here, I feel extremely frustrated working with the immigration team at Squarespace. To be clear, Squarespace has a pretty good/standard immigration policy: immediate visa sponsorship and green card sponsorship after 1y. I want to share my experience with potential candidates who might have similar immigration needs. Think twice before you join even if the HR promises you that your case will be handled professionally! I am seeing people leaving/thinking about leaving the company due to the current poor immigration service here.
• Not competitive salary in engineering, and the company is not trying to pay in the top band of the current market, thus sending away many great candidates to companies who are willing to pay more.
• Shift from Options to RSU, which is fine, but it is a private company! It means you are now granted book money and you have to pay tax for that.
• Lack of incentive for top performers. In some well-run companies in the tech industry, top performers are rewarded heavily for their hard work and great potential in the future. Squarespace doesn't appreciate that in terms of financial rewards.
• Not really startup culture. On the other side of the impact of flexible working policy, you will find the whole engineering culture quite laid back and things move quite slowly.
• Career conversations rarely happen, and you have to constantly ask for feedback and guidance on how to advance to the next level if you are ambitious about your career. Otherwise, be prepared for staying at your current level for years.
• Executives want to exercise the OKR process, but are still struggling themselves in terms of how to write OKRs effectively, how to map teams' OKRs with department and company OKRs, and more importantly, how to rate the OKRs for every quarter. For now, they just write it down and forget it the next quarter, with no ratings, no retrospection on how things went, and no incentives for good results.
• The market is great, but also competitive, and Squarespace is not among the leaders in the market. The business strategy of the company is either not smart enough or not executed well IMO.

To CEO: you are great at creating beautiful products that people love, and I really respect that! As a CEO, you also need to make sure of hiring the best talents in the market, retaining them, growing them, and relying on them to 10x the company. Not all brilliant ideas come from you, and at the current stage of the company, I think you should focus more on the talent and organization process and efficiency problems!