Not your everyday company

Lemonade completely reinvented how insurance works. As a customer-centric tech company, we created an insurance experience that is smart, instant, and delightful.

At Lemonade, you'll be working with a group of like-minded makers, who get a kick out of moving fast and delivering great products. We surround ourselves with some of the smartest, most motivated, creative people who are filled with positive energy and good karma.

Unlike most publicly traded companies, we're nimble and efficient. We take pride in the fact that we still think and operate like a startup. We don't care much about titles and hierarchy and instead focus on innovation, bold moves, and challenging the status quo.

We're built as a lean, data-driven organization that relies on a common understanding of objectives and goals to provide teams with autonomy and ownership. We don't like spending our days in meetings and we skip committees altogether. At Lemonade, there's no such thing as going over someone's head. We have zero tolerance for bureaucracy, office politics, and lean-back personalities.

As a Public Benefit Corporation and a certified B-Corp, we deliver environmental and social impact using our products and tech. Through our Giveback program, we partner with organizations such as the ACLU, New Story, The Humane Society, Malala Fund, American Red Cross, 360.org, charity: water, and dozens of others, and have donated millions towards reforestation, education, animal rights, LGBTQ+ causes, access to water, and more.

Awarded 'best workplace'

Best Workplace and Best-Led Company by Inc. Magazine

"World Changing" by Fast Company

Recognized as a World Changing Idea by Fast Company Magazine

Ranked #1 Home insurance in America

Won best renters and homeowners insurance in America by US News, and others

Best Pet Insurance in America

Rated "Best Overall Pet Insurance" by Better Homes & Gardens

Rated 4.9 on the App Store

Among the highest rated apps of all time

What you're applying for

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

Things to know...

Lemonade is an equal opportunity employer committed to diversity and inclusivity. We never discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. If you require reasonable accommodations due to religious beliefs, pregnancy, or disabilities, let us know at any time.