Pros
The engineers are mostly good people. You might learn finance things, but you won't learn good technical practices. First, this might be a pro or con of Checkout, depending on you: be aware that Checkout is a pro-cryptocurrency company. Checkout doesn't hold or make cryptocurrency, they're not an FTX. but Checkout works with cryptocurrency companies and has a head of "Crypto Strategy". The company makes profit off real money flowing in and out of cryptocurrency vendors, so they and encourage other people to waste money on cryptocurrency in general. At Checkout, you'll have to sit though all hands meetings where senior staff talk glowingly about stablecoins, NFTs or the like. It's better to choose an employer whose views align with yours on this
Cons
The rest of my observations: YMMV as the team silos are deep. This is a Westrum category 1 organisation. The engineers are mostly good people, although the ones with deep in-house technical knowledge are isolated from industry best practices, don't know what they are missing and have no incentive to learn. But autonomy is very low. Information is hoarded. Technical practices are not uniform across the board, they are patchy and there's no desire to level up. Checkout is not a company that encourages speaking openly, or saying that things could be done better. Do not expect Psychological safety. Do not expect change. The "Devops team" has "no intent" to do continuous delivery practices - they are deeply invested in outdated tools, manual testing and teams supposedly rolling their own automation, which of course these teams never have time and skills to. It's a step back in time. Management can be toxic. Some Line managers are enlightened, but some just expect micromanagement and Jira-closing feature factory behaviour, i.e. work the machine harder not smarter. It's not supportive: Some managers play politics, or bully with false stories and trivial stuff, like it's middle-school. This is left unaddressed, i.e. quietly condoned.
