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Remote, United States
Source: lemonade careers · View original posting
From lemonade's posting. “We” and “our” refer to the employer.
We're looking for a Senior Learning Designer, Leadership Development Lead to help Lemonade's managers become the kind of leaders people actually want to work for.
On our People team, you'll define what great management means at a company built on autonomy, accountability, and constant change — and then build the experiences, tools, and frameworks that make it real. As AI takes on more operational work, the bar for human leadership rises. This role exists to meet that moment.
We believe three things matter for every role at Lemonade:
driven 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
Define what great leadership looks like at Lemonade in an AI-first, autonomous org — then build the frameworks, language, and tools that make it concrete for managers day-to-day
Own our Manager Seminars end-to-end: gather feedback, update content, and sunset or redesign learning that no longer fits how we operate — keeping everything practical, immediately applicable, and true to how we lead
Partner with Manager Partners and use Manager Effectiveness data to identify skill gaps, then design learning experiences to fill them — with a focus on organizational change, AI-human team dynamics, and coaching in remote and hybrid environments
Create spaces for peer-to-peer learning through cohort discussions, live seminars, and office hours that surface what great management looks like and help leaders grow from each other
Use surveys, usage data, and feedback to track engagement; partner with People Insights to measure whether learning is improving team performance and retention — and evolve the strategy based on what you find
Unfortunately, we cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico.
Lemonade’s US base salary range for this full-time position is $100,000 - $130,000 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. Our competitive total rewards package includes comprehensive health & wellness coverage, equity, a 401(k) plan with employer match, 20 paid vacation days, and parental leave.
Speak to your recruiter to hear more about the specific salary range for your preferred location and our total rewards package.
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