Community Ops Partner - building systems that help scale membership brands and their engagement | Nonprofit Founder | Digital Wellbeing Advocate

Hey, I’m Lilly! Loneliness is one of the biggest challenges of our time, and community is one of the most powerful antidotes. But belonging doesn’t just happen on its own. Without structure, even the most inspiring communities struggle to deliver on that promise. I help founders of membership-based communities and community-driven brands put real systems behind the magic. Think: scattered onboarding steps → smooth member journeys, disconnected tools → clean workflows, one-off events → repeatable engagement cadences. How we’ll work together: • Start with a 8 week pilot to design and implement core systems (onboarding flows, engagement cadences, dashboards, and SOPs) • I’ll work ~20 hours a week as your Community Ops Partner, giving you both execution and strategic support without the cost of a full-time hire. By the end, you’ll have onboarding that works, engagement that lasts, retention you can measure, and playbooks you can scale. • Want to explore working together? DM me here or book a call here: https://calendly.com/lillycheckoff/30min A bit more about me… 🎒 At 12, I founded Tools for School, a nonprofit that has since donated 20,000+ backpacks filled with school supplies. I’ve lived through the founder chaos, and I know how much smoother it can be with the right systems. 🐨 I spent two years living in Australia and feel lucky to have called it home. The experience shaped how I think about connection, adaptability, and belonging (and no, the spiders aren’t that bad). 🗂 I’ve always been an organizer… as a kid, I ran “quarterly closet cleanouts,” color-coding my wardrobe like it was a board meeting agenda. 📱 I also write and speak about digital wellbeing, helping people (especially Gen Z) reclaim time and mental health in an always-on world.