Senior Manager, Retail Operations

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and Wirecutter). Calendar 2 launched earlier this year to rave reviews, and our newest product, Skylight Buddy, was just named one of TIME’s Best Inventions of 2026. Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable. We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks. Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us. About the Role: The Senior Manager Retail Operations will lead our retail operations team and own the long-term plan for how we ship to retailers. You will manage two Retail Operations Managers, who run the day to day for our retail accounts, and you will be the escalation point for retailer operations leaders when something goes wrong. You will also be the thought partner to our Senior Director of Global Fulfillment on the larger questions: which retailers to add, whether to go direct or