Pros
Some great people. Good work life balance. They do the business of insurance very well it seems. Very stable due to excellent underwriting. Good spot for early career professionals/recent college grads/tech hobbyists to mature. Also good for late stage careers to coast into the sunset.
Cons
Pay is far short of industry but they think they're at parity for some reason. They say it's an agile shop but it's waterfall with extra steps; "wagile" at best. Most projects I was on involved 3 architects, a PO, a PM, a scrum master, a few managers, and then two actual engineers; work that should take a week at most places will take 3 months at least at Travelers. It moves very very slowly. Have some significant skill gaps in their tech workforce; temp contractors do most of the heavy lifting. Between weak comp and forced return to office, Travelers lost most of their best tech talent. Getting anything "innovative" done is excruciating here; there is a bevy of long-tenured but mediocre tech employees that believe they're on the cutting edge but are 5-10ish years behind accepted industry best practices. They wouldn't know because a surprising number of have little to no experience outside of the company; a surprising number of "engineers" cannot code or cannot code proficiently . Very very insular; many examples of execs putting their kids/relatives into desirable positions. A fortune 100 company that somehow feels like a family business but not in a good way. Raises and bonuses are mostly linked to who you know and not your job performance. Way way way too many meetings with far too little execution. If you work in technology I wouldn't recommend spending more than a year or two here but be aware they're comp structure will penalize you for this so either plan for that ahead of time or plan to spend 3 years here.