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 understating 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 are looking for a Learning Designer to help Lemonade’s managers become the kind of leaders people actually want to work for. You’ll keep our Manager Seminars fresh and build new learning that tackles real leadership challenges—like managing in an AI-first world or leading through constant change.

This role is crucial as we scale our autonomous organization. Great managers are what make our AI-first culture work for humans. You’ll be designing the learning experiences that help our leaders navigate the unique challenges of managing at Lemonade—from coaching remote teams to leading through rapid AI adoption. This position is a critical part of the People Ops team, directly impacting team performance and retention as we continue to grow and embrace new technologies.

In this role you’ll

• Own our existing Manager Seminars from end-to-end. Gather feedback, update content, and ensure all learning is practical, immediately applicable, and aligned with how we actually lead at Lemonade.
• Partner with Manager Partners and use Manager Effectiveness data to proactively identify skill gaps. Design new learning experiences to fill these gaps, focusing on areas like organizational change management, AI-human team dynamics, and coaching in remote/hybrid environments.
• Leverage a variety of content formats to meet managers where they are, including self-paced learning (eLearning, podcasts, Slack nudges), live seminars, practical toolkits, and one-page resources.
• Design content—such as templates, conversation guides, and reflection prompts—that managers can seamlessly use in their day-to-day work, meetings, and existing workflows.
• Build spaces for peer-to-peer learning—including cohort discussions, live seminars, and office hours—to showcase what great management looks like and help leaders grow from each other’s successes.
• Utilize surveys, usage data, and feedback to track content engagement. Partner with People Insights to determine if manager learning is improving team performance and retention, and use those insights to continually evolve the learning strategy.

What you’ll need

• 3+ years of experience in learning design, leadership development, or management training—you should understand what makes managers tick and what they actually need
• Bachelor’s degree in Education, Psychology, Business, or a related field (or equivalent experience)
• Ability to design practical, immediately useful content that managers can apply right away (not theoretical frameworks)
• Experience with learning management systems, content creation tools, and data analysis for measuring learning impact
• Excellent written and verbal communication skills, especially for translating leadership concepts into actionable tools
• Adaptability, drive, and an efficiency mindset — we believe these matter most in human-AI collaboration
• Background in people management or close partnership with managers—you’ve either been one or worked closely with them to understand their real challenges
• Collaborative approach with experience partnering across People, operations, and leadership teams
• Understanding of modern management challenges, especially in remote/hybrid environments and AI-integrated workplaces
• Ability to work in a remote environment
• Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture

*Please note that we are unable to sponsor applicants for work visas

Unfortunately, we cannot consider applicants from these states; Colorado, California, Montana, Hawaii, New Mexico and Puerto Rico.

Lemonade’s US base salary range for this full-time position is $75,000 – $100,000 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Speak to your recruiter to hear more about the specific salary range for your preferred location.

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.