Chief AI Officer Application Deadline: 19 June 2026 Department: Operations Employment Type: Permanent - Full Time Location: Remote Description At SafetyWing (YC W18), we’re building a global social safety net for remote workers - simple health, insurance, and retirement products designed to replace national welfare systems. Our mission is to remove geographical borders as a barrier to equal opportunity and freedom for everyone. If we succeed, we believe this will be one of the most important tasks of our time. 🌎 About this Role We believe AI is the biggest opportunity to amplify human potential that we've seen in decades. Your job is to embed AI throughout SafetyWing - across our operations, products, and ways of working. You'll have a blank canvas. You'll help define how AI is used across the company, identify the highest-leverage opportunities, build systems and workflows, train teams, and influence our product roadmap. You'll work closely with leaders across SafetyWing to rethink how work gets done and what an AI-native insurance company should look like. Success in this role means that a year from now, people at SafetyWing can accomplish things that feel impossible today. AI should make every team smarter, more creative, more effective, and capable of delivering far more value to our members than a company of our size normally could. 👩‍💻Your responsibilities will include Define and execute SafetyWing's AI strategy so that every team, workflow, and product becomes meaningfully more capable with AI Build, test, and deploy AI-powered solutions across operations, claims, support, growth, product, design, and beyond Help shape SafetyWing's product roadmap so AI is embedded into what we build, not just how we work Help every team member become exceptionally effective with AI through training, coaching, experimentation, and hands-on support Reimagine how work gets done at SafetyWing from the top down. Not only removing busy work and creating new ways for people to operate, but thinking deeply about how an AI-native insurance company should run internally and how AI should be embedded throughout our products Measure the impact of AI across the company and continuously raise the bar for what our team can accomplish 🧪 We are looking for someone who Lives and breathes AI and is constantly experimenting with new models, tools, and workflows Has built AI-powered systems across a variety of use cases, especially in operations Has experience as a senior leader and knows how to influence, align, and drive change across an entire organization Can help both technical and non-technical teams adopt new ways of working Is comfortable switching between hands-on execution and long-term strategy Has a clear way to measure and demonstrate impact 😀 We like to work with people who Want to help build a global social safety net on the Internet. Think for themselves instead of copying others. Are willing to try new things, even with the risk of failure. Are intellectually curious and open to new ideas. Are creative and bold in the face of any problems. Have strong integrity and do the right thing. 🧘 Beyond your base rate, we offer: Fully remote work environment – work from anywhere globally Unlimited time off Equity compensation Our own Global Safety Net, giving you worldwide health, income, and travel coverage Personal development and office budgets A new laptop when you need one Annual team gathering in amazing locations - our previous meetups were in Iceland, Vietnam and Argentina 🚀 We look forward to hearing from you!