Matt MacInnis

Chief Product Officer (formerly Chief Operating Officer) at Rippling ($16B+ valuation, 5,000+ employees). Previously founded and ran Inkling (digital content platform, 2009–2018). Early investor in Notion, Rippling, and ~70 companies. Former Apple employee under Steve Jobs. Known for unusually blunt management philosophy: deliberate understaffing, the power law + entropy frame for understanding why intensity must be sustained, the alpha/beta framework for matching people and processes to product contexts, the PQL (Product Quality List) for lightweight quality enforcement, and a public critique of “never quit” culture as VC-aligned propaganda at the expense of founders.

Episodes in this wiki

• Matt MacInnis on Extraordinary Efforts, Power Law and Entropy, and Building Rippling — Lenny’s Podcast (~2025)