Block

• The people were awesome.
• There was an ambiguous work environment (in a good way!).
• The tooling was great, and working cross-functionally was easy while remote.
• I shipped some awesome products.
• Internal mobility was great, and I really grew at the company.

• Leadership was out of touch.
• There was a forcing of AI across everything.
• The restructure was constant. The fear of layoffs was heavy, and they did eventually happen.
• The work-life balance suffered. Due to Slack, you were always on, and it was necessary to continue communicating after hours.

Economic empowerment is what Square preaches, but they eventually laid off over forty percent of their workforce.

Square started as a company that wanted to empower the small and medium-sized businesses of the world, but is now trying to gain stadium deals and grow into the strategic business sector. This is likely due to Wall Street influence, the stock price, and wanting continued high-volume growth.

My advice, which is too late, would be to stick to the SMB sectors and own it. The continued shift of direction has given competitors an advantage, which layoffs won't resolve.