Pros: Using ChatGPT to summarise and articulate my thoughts below: 1. Remarkable Growth and Potential: Rippling is experiencing high growth and enormous potential. It's impressive to witness how the company maintains such rapid expansion at this scale, both in product offerings and customer base. 2. Engineering-Driven Culture: The company is heavily invested and driven by engineering, allowing engineers to see their impact in production within hours. This immediate feedback loop is empowering and makes the work feel meaningful. 3. Significant Improvement in Recent Years: Over the past two years, Rippling has seen notable advancements. Certain teams operate with a 1-100 approach, focusing on engineering and operational excellence, which greatly enhances engineering potential and provides opportunities for growth. 4. Dynamic Work Environment: Rippling is like a competitive sport. It’s challenging yet enjoyable, and employees are encouraged to play to their strengths. 5. Customer-Centric Engineering: Engineers at Rippling directly experience customer problems. When encountering product gaps or support tickets, they understand the user's perspective and feel their pain because they use the product themselves. 6. Open Communication Culture: Rippling promotes open communication where team members challenge each other directly. This culture eliminates unnecessary formalities and focuses on building disruptive market solutions. 7. Empathetic Executive and Engineering Team: The executive team demonstrates deep empathy for their customers, often going above and beyond to provide support. The employees at Rippling are humble and collaborative, fostering a supportive and empathetic team environment. It depends on a team-to-team basis, but I have seen this general pattern in most of the teams. 8. CEO's Direct Involvement: The CEO's close connection to the product gives him a unique position to steer the company towards continued high growth, making him a key factor in Rippling's enhanced potential.

Cons: 1. Legacy Tech Debt: Like many rapidly growing companies, Rippling has accumulated tech debt in its legacy products. However, the company is adept at identifying which debts to address immediately and which can be deferred. 2. Complex Business Context: The extensive business context at Rippling can make onboarding feel overwhelming. Nonetheless, teams are generally supportive and help new employees acclimate quickly. 3. Heavy Engineering Focus: Rippling emphasizes engineering execution, with the expectation that everyone, including those in senior roles, contributes to coding. While this is beneficial for maintaining technical excellence and rewarding for most technical folks, it may also be off-putting to some professionals who prefer a different balance of responsibilities.

Pros: Good comp; not too much bureaucracy.

Cons: Not technically challenging work; lots of tech debt.

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.