Pros: If you want to make money and want to escape corporate politics

Cons: WLB can be tough on payroll teams.

Pros: Leadership: C-levels are transparent and approachable. Most importantly, they've led Rippling on a great trajectory and have ambitious but reasonable goals. Coworkers: People are competent and easy to work with across all functions. Those that don't meet the bar are quickly managed out. Career growth: For those that want it, Rippling has plenty of opportunities to take on outsized scope and build new products. Rippling rewards high performers meaningfully.

Cons: - Benefits: Health insurance is expensive with dependents. There is no 401k match, which is unfortunate but understandable at Rippling's current stage. - Work-life balance: Compared to past jobs, I have been consistently very busy at Rippling during my tenure here. Rippling can be challenging for those with family and other life commitments.

Pros: Rippling is the most Engineering-driven company I've worked at in my career. The culture recognizes that a lot of things are possible with the right technical investment. The company actually uses its own products for everything, so if something is bad, it gets fixed. Rippling expects you to be engaged, and you'll be rewarded with agency. Engineers aren't overburdened with process. There's still a strong startup vibe; the pace is fast and things actually get done. There's a lot of opportunity to influence the organization and establish long-term direction. On the business side, execs are generally as transparent as you could reasonably hope for. The CEO still has open-ended chats with the whole company frequently.

Cons: Tech debt is burning down, but slowly. The software development lifecycle is still underdeveloped. If you cannot advocate for yourself, you'll find the pace challenging.