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'llBuild 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
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
Skills Required
- 7+ years of experience across IT engineering, internal products, automation, business systems, technical operations, or adjacent roles
- 3+ years leading and developing technical teams
- Strong problem abstraction and ability to structure and solve ambiguous business problems
- Technical credibility partnering with Product, Engineering, Operations, and Security
- Strong understanding of AI, APIs, data flows, integrations, MCPs, security, and scalable system design
- Experience with Claude, Cursor, Workato, or similar platforms
- Ability to prototype with Python, TypeScript, Ruby, or comparable languages
- Strong communication and upward-management skills
- Track record of creating direction, developing others, and shipping meaningful outcomes
- Willingness to work in an office environment most days of the week
Lemonade Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Lemonade and has not been reviewed or approved by Lemonade.
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Healthcare Strength — Cigna-administered medical plans provide multiple options (EPO/OAP/OAPIN/HDHP) alongside dental, vision, prescription coverage, disability, and life/AD&D. 2026 plan materials and state notices indicate broad essential health benefits with mainstream networks.
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Retirement Support — A tiered 401(k) match structure is documented, offering meaningful employer contributions when employees save. This complements equity grants/RSUs that are commonly included in total rewards.
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Leave & Time Off Breadth — Employee-reported baselines around defined PTO and company holidays, plus flexible sick time, position time off as a strength. Parental leave is frequently described as generous for the U.S. context, though candidates should confirm current specifics.
Lemonade Insights
What We Do
Our mission is simple: Create the world’s most loved insurance through technology and social impact. As a certified Public Benefit Corporation and B-Corp, Lemonade is constantly challenging how the insurance industry does business. We’re creating an experience that is fast, affordable, and hassle-free across renters, homeowners, pet, life and car insurance. And through our annual Giveback program, in which leftover premiums are donated to charities our customers choose, we’ve donated nearly $5 million to a variety of organizations in need.
Why Work With Us
We’ve set out to make insurance loveable, fast, simple, and socially impactful - words that aren’t often associated with this industry. We’re a Certified B-corp, the only US insurance company to never invest in polluting industries, and our annual Giveback program has donated nearly $5 million globally to nonprofits in need.
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