Senior Security Engineer

We're looking for a Senior Security Engineer to help secure Lemonade's applications, infrastructure, and the agentic systems we're building for the future of insurance. You'll be part of a small, sharp security team that works horizontally across the entire organization — from AI and application security, to cloud and IT security, and beyond. This isn't a narrow, siloed role. You'll own meaningful domains, drive automation that lets the team scale, and help shape how security works at a company that's genuinely reimagining what insurance can be. The team has built an in-house AI security platform, and you'll build your agents on top of it. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. IN THIS ROLE YOU'LL - Build and maintain automation systems and AI agents that minimize manual security work and help the team scale - Code internal security tools in TypeScript and/or Python that the team relies on and builds from - Evaluate third-party security tools and vendors, and take ownership of the ones we adopt - Identify new attack vectors and security gaps proactively — before they become problems - Partner with product, cloud, and IT teams on security design as new features and infrastructure take shape - Support security operations across the organization — from triaging alerts and incidents to reviewing code for vulnerabilities, as you grow into the role WHAT YOU'LL NEED - 5+ years in security engineering, with a strong application security or development foundation - Hands-on coding ability — you'll write automation, tooling, and agents, primarily in TypeScript and/or Python (strong TypeScript or Python skills are required) - Solid grasp of the software development lifecycle and how security integrates across all its layers - Experience with cloud environments, AWS preferred — familiarity with AWS is a meaningful advantage - Comfort working in ambiguous environments where priorities shift - A proactive mindset — you spot gaps before they're reported, and you fill them - Clear communication skills to translate security risks for non-security audiences - Ready to work in an office environment most days of the week