IT & AI Ops Leader for Autonomous Maker Experience

Lemonade; United States; On-site; USD 127,000 - 194,000; Full time

Job summary

Lemonade in Tel Aviv seeks a product-minded IT leader to scale internal work delivery, head IT, and drive autonomous Maker experiences with Product, Engineering and Security. You will manage IT Solutionists and prototype AI-powered automations.

Lead AI opportunities from discovery to rollout, align tech with Lemonade's mission, and ensure security governance across the org. This role requires hands-on system design and strong collaboration.

Qualifications

• 7+ years across IT engineering, internal products, automation or related roles.
• 3+ years leading and developing technical teams.
• Strong ability to structure and solve ambiguous business problems.
• Technical credibility to work with Product, Engineering, Operations, and Security.
• Solid understanding of AI, APIs, data flows, integrations, security and scalable system design.
• Experience with Claude, Cursor or similar platforms.
• Prototyping with Python, TypeScript or Ruby.

Responsibilities

• 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.

Skills

People leadership

Automation design

AI integration

Cross-functional

Coding prototyping

API integration

Python/TypeScript/Ruby

Tools

Claude

Cursor

Workato

Job description

Lemonade in Tel Aviv seeks a product-minded IT leader to scale internal work delivery, head IT, and drive autonomous Maker experiences with Product, Engineering and Security. You will manage IT Solutionists and prototype AI-powered automations.

Lead AI opportunities from discovery to rollout, align tech with Lemonade's mission, and ensure security governance across the org. This role requires hands-on system design and strong collaboration.