Pros: Motivated colleagues and endless features to build. Seasoned CEO, Strong market fit.

Cons: Development favored velocity over sustainable practices and well-considered decisions. No one felt empowered to say no.

Pros: Great culture: everyone gets a ton of ownership & opportunities to make a big impact. Competitive pay/equity. Talented & nice people. You can have fun while working hard.

Cons: Growing pains: Process changes are painful but mostly expected for a company at this growth rate & scale. Work-life balance can be challenging. Definitely not for everyone. Benefits are mediocre.

Pros: - I feel like I have a lot of autonomy over figuring out what to work on and how to implement it. - Growing really fast, the future looks bright, which I think keeps most people motivated to do a good job. - I think basically everyone on engineering is trying to do a good job and usually has the skills to back it up. - It's a relatively younger-leaning crowd, which is something that I've enjoyed over other older-leaning companies I've worked at, culture-wise.

Cons: There's a good amount of tech debt that slows things down and makes things difficult to understand. We're in a heavy growth phase, so this is mostly a backburner issue (probably rightfully so), even though it increases overall workload. Some teams often make technical decisions which seem very questionable, at least from the outside looking in. This leads to crazy complicated issues that are tough to undo. There's an infinite amount of work to do, so it's up to you to control and manage it. The variance in code quality that some engineers/teams have versus others is pretty jarring. I'm sure everyone who gets promoted has done things to deserve it, but there are times when people at a higher level than me in the eng org do something as basic as not communicating important things to dependent teams in pursuit of a fast timeline. This creates a multi-week fiasco to try to patch it up. Sometimes, it shows that some people perhaps got promoted too quickly to a relatively high role, or are under so much pressure to deliver (often very directly from the CEO) that they forget to do some basic things. I know the cons list is longer than the pros list, but overall, if you either know or learn to control your career as an engineer, you'll probably be fine, grow a bunch, and make great comp if Rippling IPOs.