Rippling and the Return of Ambition

Reminiscent of the foundational computing companies, Rippling shows what ambition in modern business software looks like. In the age of software incrementalism, Rippling is an anachronism.

Rippling rejects these norms entirely. It ignores the mimetic warfare of the Gartner quadrant. Its wedge was a data asset, not a narrow product. It doesn’t let SaaS metrics dictate its strategy.

SaaS wisdom teaches us narrow lessons: start by conquering a narrow market and expand from there, add at least as much in ARR as you burn each year, and build your product either horizontally or vertically.

If Rippling becomes the system of record for employee data, it will rewire the entire business software landscape. With a breadth of software integrations, Rippling can become the connective tissue across traditionally siloed applications. 

Each micro-startup gets to leverage the technical infrastructure, distribution engine, and existing customer base of a large company. But the GM model requires complex coordination of resources across the company – new product leaders need to push the marketing team to highlight their capabilities, train the sales team on selling their product, and... See more

Rippling’s expansive product strategy requires a unique modular org structure. Each product has a relatively autonomous GM and engineering team. Given each sub-product has massive scope, they’re like startups within a bigger startup. In fact, Rippling has over 50 former founders within the company, many of whom are running various product divisions... See more

Unconventional for a company of Rippling’s size, Parker has no executive assistant. This means you can’t simply slide onto his calendar. The result is that he spends far less of his time in meetings, and far more on product, than the average founder. A compound product requires undivided attention. 

Bundling is a tailwind to sales conversations. Why pay $30 per employee per month for five different products ($150) if you can get a comparable offering in a single bundle for $50? And companies with smaller budgets can buy additional products that were out of reach as point solutions. This is one of the few true accumulating advantages in softwar... See more

Rippling customers can configure custom workflows that allow salespeople to give customer pricing discounts based on their level within the org. Or ingest Zendesk tickets to see payroll costs per support ticket resolved. Or run reports across silos of business data.