I havent been at Bench for over 6 years but it’s always been a business on the verge of failure. The main issue was just the schizophrenic strategy that was being employed. On one hand you have a software company with useful tools and services to automate bookeeping. On the other you had a division of bookeepers that would do a lot of the manual / refinement work. These tasks are at odds with one another. If you automate things you remove power from the teams who are incentivized to scale their org charts. With LLMs, Bench should have been positioned to own this space entirely, and offer a superior or equivalent product with much better margins. Bur they decided to become a services company and not a technology company.
All I can take away from it is a few lessons, because this is a pretty awful outcome for almost every party.