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 business-minded, technically strong leader to lead Business Applications at Lemonade and play a key role in building a more autonomous company. You'll lead a team that works across Lemonade to understand complex business challenges and turn them into technology solutions - from AI agents and automation to custom solutions, integrations, and enterprise platforms. Doing this well takes a deep understanding of how the business works and the instinct to spot where technology can create genuine leverage.

We believe two things matter for every leadership role at Lemonade: leadership that sets the bar for excellence, builds high performing teams, and holds them accountable, and strategy that thinks several years ahead and turns ambitious plans into reality. 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

• Turn business challenges into working technology solutions - partnering with leaders across Lemonade to find where AI and automation can materially change how work gets done
• Build toward a more autonomous Lemonade by identifying where work can be fundamentally redesigned through agents, AI, and software - then leading the team in making it real
• Own problems end-to-end, from getting deep into the business challenge, through implementation, adoption, and measurable outcome
• Shape a forward-deployed BizApps model where the team works close to the business, moves quickly, prototypes fast, and shares accountability for results
• Lead and grow a strong team that combines business understanding, product thinking, and technical depth - raising the bar for ownership, curiosity, and speed
• Set the strategy and technical direction for the platforms, integrations, and data flows that power teams across Lemonade

What you'll need

• 7+ years leading technology solutions for business applications/operations, with experience managing and developing a team.
• Strong business judgment - you can quickly map how a function works, what drives its outcomes, and where technology creates real leverage
• Strong technical fluency across architecture, APIs, integrations, data, and automation (enough to evaluate solutions and confidently guide technical decisions)
• Hands-on familiarity with modern AI capabilities, including LLMs, agents, and AI-enabled development, and genuine curiosity about where it's headed
• A track record of turning complex, ambiguous business problems into solutions with measurable impact
• Strong product thinking - you start with the problem, challenge requirements, prioritize by impact, and care whether what you build actually gets used
• Experience partnering with senior stakeholders on cross-functional, high-ambiguity problems
• A college degree in a relevant field
• 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.