We're looking for a product-minded IT leader to help Lemonade scale how teams get work done internally. You'll lead IT in Tel Aviv, manage a team of IT Solutionists, and build more autonomous Maker experiences - partnering across Product, Engineering, and Security to turn business needs into coherent strategies, systems, and automations using AI-powered products.

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 execute the Autonomous Maker Experience across the employee lifecycle, workplace technology, and technical support

• Manage and develop IT Solutionists into stronger owners, builders, and advisers

• Partner with leadership to identify, frame, and prioritize high-impact automation and AI opportunities

• Apply problem decomposition and system design to turn incomplete ideas into clear plans and recommendations

• Personally prototype and build automations, agents, workflows, and internal tools

• Own cross-functional AI opportunities from discovery through rollout, adoption, and impact measurement

• Own the Tel Aviv tech experience - networks, AV, MSPs, vendors, budgets, AI governance, and Security partnership

• Build solutions that fit cohesively into Lemonade's wider agentic systems and Maker experience

What you'll need

• 7+ years across IT engineering, internal products, automation, business systems, technical operations, or adjacent roles

• 3+ years leading and developing technical teams

• Strong problem abstractions and the ability to structure and solve ambiguous business problems

• Technical credibility to work as a peer with Product, Engineering, Operations, and Security

• Strong understanding of AI, APIs, data flows, integrations, MCPs, security, and scalable system design

• Experience with tools such as Claude, Cursor, Workato, or similar platforms

• Comfort prototyping with Python, TypeScript, Ruby, or comparable languages

• Strong communication and upward-management skills

• A track record of creating direction, developing others, and shipping meaningful outcomes

• Ready to work in an office environment most days of the week