Lack of clear direction for the business from leadership. They tried to do too much with the product without really understanding what the customer needs or wants.
Not enough passion or desire to truly solve the problems of B2B marketers - the business was started as a media company and happened to pivot into B2B marketing. No one on the founding team or the current leadership team have experience or passion in the space they're serving.
Very diluted cap table with a disparate board that seems to be chalking up the business to the bottom half of their portfolio vs. ensuring a positive exit. AKA - your equity is worth very little at Kapost and there is not clear exit strategy.
CEO does not know how to manage his managers and has made poor hiring and promotion decisions. Feels more comfortable getting in the weeds in whichever department is struggling that quarter vs. running a balanced approach to the business. One specific example is the current VP of Marketing. She was a great Sales Training and has done sales throughout her career, but was placed into the VP of Marketing role to fill the gap the CEO left after running marketing post-RIF.
All in all, if you're looking for a startup that is stable, on the path to a positive exit, will develop and push you professionally, and management/executives you can learn from - DON'T GO TO KAPOST!