TLDR, company used to be great before layoffs last year, since then it's been very painfully downhill.
The company was acquired by Zinnia recently, and the acquisition does not seem to be going well from the perspective of the tech department. It reminds me of the worst parts of Succession, but also of an episode from the Sopranos called "Bust-Out", if you've seen that--a kind of hostile gutting of a company bought for parts and taken apart until there is nothing left.
The new CEO, Michele Trogni, seems to have no clue about how to run a cutting-edge tech company, and yet she is attempting to do exactly that. When talking about finance, and about the players in that space, she seems quite adept and knowledgeable. She has experience as head of tech at UBS, but I'm curious how the tech at somewhat dinosaurs like that would compare to that at a more competent modern tech company.
What she seems to excel at is a kind of top-down cutthroat capitalism. This is starkly at odds with the work culture that Policygenius had built over the years, and from my understanding it is alienating all the workers in the tech department. Many very talented engineers made the choice to work at Policygenius in large part because of the work culture, and with that gone, the rationale for staying also goes.
Like Elon Musk at Twitter (down ~60% in value in over a year), she seems to be gambling on the unproven hypothesis that tech workers can be treated very badly and will put up with it. She is cutting costs aggressively and seems to be moving toward firing people (which is possibly her greatest "strength", just Google her history at UBS).
There is no coherent retention strategy for tech workers, and so the only conclusion one can draw is that either her leadership is incompetent and they did not have a clear plan for this acquisition, or (my guess) she intentionally wants people to leave to cut costs.
The problem with this strategy is that the number of departures may cross over a critical threshold, after which they will have a really hard time supporting the relatively complex systems at the company. The best people will leave quickly, and the rest will maybe quit next year. I'd be surprised if more than 30% of the current tech staff was still there in a year's time.
Overall, for tech workers, it has shifted from a pretty good collaborative culture where colleagues had agency and felt supported, to a top-down corporate nightmare cloaked in corporate platitudes, a string of endlessly bad news from the top, a place where it regularly becomes difficult to do one's job because of all the disruptive organizational churn and depressing corporate intrigue.