Senior Leadership Learning Designer — AI-First, Remote

Lemonade, Inc.; United States; Remote; USD 100,000 - 130,000; Full time

Benefits offered by this job

Equity

Health benefits

401(k) with employer match

20 paid vacation days

Parental leave

Job summary

Lemonade, Inc. is seeking a Senior Learning Designer, Leadership Development Lead to elevate Lemonade's managers into trusted, effective leaders in an AI-enabled, autonomous organization.

You'll design, own, and evolve leadership programs with a focus on AI-human collaboration, remote and hybrid leadership, and practical tools that managers can apply immediately. This role offers remote work within the United States and a competitive rewards package.

Qualifications

• 4+ years of experience in learning design, leadership development, or management training.
• Background in people management or close partnership with managers.
• Experience with learning management systems, content creation tools, and data analysis to measure learning impact.
• Strong written and verbal communication skills for translating leadership concepts into tools people actually use.

Responsibilities

• 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.
• 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.
• Experiment rapidly with new learning formats — treat each program like a product launch, with clear hypotheses, fast iteration, and honest retrospectives.
• Meet managers where they are by using a variety of formats: self-paced eLearning, podcasts, Slack nudges, live seminars, practical toolkits, and one-page resources.
• Build content managers can use the same day — conversation guides, templates, and reflection prompts that fit seamlessly into meetings and existing workflows.
• 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

Skills

Learning design

Leadership development

People management

LMS experience

Content creation

Data analysis

Strong communication

Cross-functional collaboration

Remote work

Tools

Learning Management Systems (LMS)

Job description

Lemonade, Inc. is seeking a Senior Learning Designer, Leadership Development Lead to elevate Lemonade's managers into trusted, effective leaders in an AI-enabled, autonomous organization.

You'll design, own, and evolve leadership programs with a focus on AI-human collaboration, remote and hybrid leadership, and practical tools that managers can apply immediately. This role offers remote work within the United States and a competitive rewards package.