In a phrase: lack of communication.
The company starts you off slowly and really eases you into handling claims with the horrendous system lemonade uses. However, once you are in the deep end you will be drowning until you are put on a CA and are ultimately fired, take a medical leave of absence, or just straight up quit. In the time I worked at lemonade I knew of at least a dozen people who had to take a medical leave of absence to focus on their mental health, myself included. This is all made worse by the fact that the primary frustration of the job is the way claims are being handled changes week over week, along with, our job descriptions. During the hiring that took place from 2018-2021 all claims adjusters were promised that the job would not be like a call-center. This stopped being true quite early on in the pandemic when Lemonade decided to terminate the employees that helped assist for incoming calls.
More on the constant changes to the working environment: at least once every 3 or so months the company will re-analyze the legal language of its policy so that a denial or approval can instantly be changed. The system we used to handle claims was an absolute disaster and would crash at least once a week which would result in some less than stellar phone calls with customers looking for a resolution to their claim. This all pales in comparison to the rampant favoritism that is offered to both certain employees and customers. If you make a big enough stink as a customer and have a big enough social media following, lemonade will bend to your every whim to save face, I witnessed this occur on numerous occasions while working there. Managers will also purposefully hold you back with the claim of "you aren't prepared for this position" and turn around and offer it to someone with significantly less experience in insurance and at the company, but since that person is popular and drinks the proverbial lemonade their upward progression is only limited by their own imagination. Only been a customer service rep for 6 months and want to work in underwriting? Do enough brown-nosing and the job is yours.
Outside of the abhorrent working conditions there is also a very, very serious issue with how the company is being managed by the CEO's (yes, there's two of them). A bonus for being hired at lemonade was large number of shares of stock that accrued over 4 years. The amount of stock promised to new employees is decided haphazardly with some being promised 1000, others 500 and some 5,000. There is only 1 small problem, the CEO (Daniel Schreiber) Dumped all of his stock roughly 6 months after the company IPO'd and peaked at a share price of 163.93. All of this information is public knowledge, but there is a direct correlation between lemonades stock value and the dumps Daniel Schreiber executed. Coincidentally, overall management throughout the company began to suffer more and more once Daniel literally and figuratively checked out.
This company amounts to nothing more than a smudge on your resume and a guaranteed need for a therapist or a regular visit to a rage room.
