First and foremost, you'll be a core member of our DevOps team. In addition, you will lead the Fin Ops aspects of the team, bridge infrastructure and financial optimization, building cost-efficient systems that scale with our AI-driven growth. This role combines deep DevOps expertise with financial accountability—automating cost management, optimizing cloud spend across multiple cloud providers, and ensuring our infrastructure investments drive maximum business value.

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:

• Drive Fin Ops strategy: Build automated cost monitoring, forecasting, and optimization tools that give teams real-time visibility into infrastructure spend and ROI

• Develop cost-aware Infrastructure as Code: Use Pulumi and Kubernetes operators to deploy infrastructure that's both performant and cost-optimized from day one

• Optimize multi-cloud environments: Maintain and enhance Kubernetes clusters across development stages while continuously analyzing and reducing cloud costs across AWS/Azure/GCP

• Create financial guardrails: Implement automated budget controls, cost alerts, and resource optimization policies that prevent runaway spending without slowing innovation

• Partner with engineering teams: Provide cost-conscious guidance, tools, and support for infrastructure decisions, helping teams understand the financial impact of their technical choices

• Lead cost incident response: Participate in both technical incident management and cost anomaly detection, conducting root cause analysis for both performance and spending issues

• Scale cost efficiency: Build monitoring and observability solutions that track not just system health, but cost per transaction, feature, and customer segment

WHAT YOU'LL NEED:

• 5+ years DevOps experience with proven track record of managing infrastructure costs and financial optimization in cloud environments

• Cloud financial expertise: Deep experience with AWS/Azure/GCP cost management tools, billing APIs, and Fin Ops best practices—a must

• Infrastructure automation mastery: Hands-on experience with cloud provisioning tools (Terraform/Pulumi/Crossplane) and cost-aware infrastructure design—a must

• Kubernetes cost optimization: Experience with K8S resource management, including cost-efficient Helm/Operators implementation and cluster rightsizing—a must

• Financial programming skills: Experience writing complex code and tools that integrate financial data with infrastructure management for large codebases—a must

• CI/CD cost awareness: Experience with Jenkins/Argo/GitLab and understanding how deployment patterns impact cloud spending—an advantage

• Financial observability: Experience with cost monitoring tools alongside traditional observability (Prometheus/Grafana/Data Dog + Cloud Health/Spot/etc.)—an advantage

• Office collaboration: Ability to work in an office environment a minimum of 3 days a week

• AI-first mindset: Enthusiasm about learning and adapting to the exciting world of AI—a commitment to exploring this field is a fundamental part of our culture

• Ready to work in an office environment most days a week

• Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture