1. You will not grow here.
The work gets repetitive for both developers and designers. You will always be spinning up the same Rails app, designing the same dashboards, using the same technology and tools in every project.
There's no career growth, nor do the annual raises make up for lack of promotions. Salaries are not competitive.
thoughtbot still focuses heavily on Rails, despite developers wanting to use other languages and modernize their skillset. The dev work is starting to feel dated.
2. The culture is on the decline.
In the past few years, thoughtbot experienced rapid expansion, followed by offices being shut down, a wave of people quitting, and others getting fired. Company culture is ill-defined after so much turnover and uncertainty.
Because thoughtbot is a distributed team, each office has a slightly different "culture" and it creates rifts in the company. They have not figured out how to make the company feel more cohesive. As time passes, these rifts become more obvious.
thoughtbot presents itself as being an inclusive environment, but everyone they've fired has been an under-represented person in tech (women, people of color, etc) while upper management is entirely white men, as is the majority of the company. This pattern has not gone unnoticed and morale is especially low among these groups.
thoughtbot expects developers and designers to handle sales, rather than hiring experienced salespeople. This has led to more and more bad projects, further frustrating developers and designers. This boredom and resentment only grows.
3. There's no direction.
While thoughtbot prides itself on being transparent, it's unclear where the company's heading. How will offices and teams be supported after so much turnover? What steps will management take to improve the company culture? How will they ensure that people do keep growing, rather than stagnating?