---
title: 'Senior Learning Designer, Leadership Development at Lemonade'
canonical: 'https://feeny.ai/job/senior-learning-designer-leadership-development-lemonade-new-york-qmfckz7q3z2k'
type: 'job'
last_seen: '2026-09-06'
---

# Senior Learning Designer, Leadership Development at Lemonade

- **Company:** Lemonade
- **Location:** New York, NY
- **Compensation:** $100k–$130k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-06-01
- **Last confirmed live:** 2026-09-06
- **Apply:** https://jobs.ashbyhq.com/lemonade/a1eb0625-40de-4e1a-992f-8f5bdc1af1d7/application

**Skills:** Learning Management Systems, Content creation tools, Data analysis

> Design and build leadership development programs, frameworks, and tools to help managers become effective leaders in an AI-first, autonomous organization. Own the end-to-end lifecycle of learning experiences, from identifying skill gaps to measuring impact.

## Job description

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
- 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

## WHAT YOU'LL NEED

- 4+ years of experience in learning design, leadership development, or management training — you understand what managers actually need, not just what looks good on a slide
- Startup or high-growth company experience — you're comfortable with ambiguity, fast change, and building from scratch
- An ownership mindset: you spot problems, propose solutions, and take accountability for outcomes without waiting to be asked
- Ability to design practical, immediately useful content that managers can apply right away — not theoretical frameworks that collect dust
- Background in people management or close partnership with managers — you've either led a team or worked alongside them closely enough to understand their real challenges
- Experience with learning management systems, content creation tools, and data analysis to measure learning impact
- Strong written and verbal communication skills, especially for translating leadership concepts into tools people actually use
- A collaborative approach with experience working across People, Operations, and Leadership teams
- Deep understanding of modern management challenges, especially in remote and hybrid environments and AI-integrated workplaces
- Ability to work in our Soho office 3 days per week
- 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

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.

## About Lemonade

## Company Overview
- **One-liner**: Lemonade is a digital insurance company that uses artificial intelligence and behavioral economics to offer renters, homeowners, pet, car, and life insurance, with a social impact model that donates unused premiums to causes customers choose.
- **Entity Type**: Public (NYSE: LMND)
- **Headquarters**: New York, New York, USA
- **Founded**: 2015
- **Founders**: Daniel Schreiber and Shai Wininger

## Core Business
- Primary industry/industries: Insurance (property & casualty, pet, life), Fintech, Insurtech
- Target customers: B2C (individuals and families), primarily digitally-native and socially-conscious consumers
- Mission or purpose statement: "Create the world’s most loved insurance through technology and social impact." [lemonade.com](https://www.lemonade.com/) Lemonade is a Public Benefit Corporation and certified B-Corp.

## Products & Services
For each major offering:
- **Renters Insurance**: Coverage for personal belongings and liability, typically acquired in ~90 seconds via the app.
- **Homeowners Insurance**: Protection for homes and their contents.
- **Pet Health Insurance**: Health coverage for dogs and cats, including accidents, illnesses, and routine care.
- **Car Insurance**: Standard auto coverage, plus a new, first-of-its-kind **Autonomous Car Insurance** for self-driving vehicles (launched in 2026, priced ~50% lower than human-driven per-mile rate). [lemonade.com](https://www.lemonade.com/investor)
- **Term Life Insurance**: Life insurance policies to protect loved ones.
- **Claims Experience**: AI-powered claims processing, with nearly half of claims paid in seconds and a record of 3 seconds to get paid. [lemonade.com](https://www.lemonade.com/)

## Market Standing
- **Valuation/Market Cap**: Not publicly available from the provided search results (market cap fluctuates with stock price; check current NYSE: LMND).
- **Key Metric (Annual Revenue)**: Q1 2026 revenue grew 71% YoY to $258M. In-force premium (IFP) reached $1.33B, +32% YoY. [lemonade.com](https://www.lemonade.com/investor)
- **Notable Investors/Partners**: Reinsured by "the most trusted names on the planet" (A-rated). [lemonade.com](https://www.lemonade.com/) Partnered with Tesla for Autonomous Car insurance. [lemonade.com](https://www.lemonade.com/investor)
- **Growth Signals**: 3.14 million customers (+23% YoY); 10th consecutive quarter of accelerating IFP growth; Adj. free cash flow of $17M in Q1 2026; positive Adj. EBITDA expected in Q4 2026. [lemonade.com](https://www.lemonade.com/investor)

## Competitive Advantages
- **AI-First, Instant Everything**: Core differentiator is using AI to deliver policies in ~90 seconds and pay claims in seconds, creating a vastly superior customer experience compared to traditional insurers.
- **Social Impact Model (Giveback)**: A Public Benefit Corporation and B-Corp. Unused premiums are donated to charities chosen by customers. This aligns customer and company incentives, reducing fraud and building brand loyalty. Over $10M donated. [builtin.com](https://builtin.com/company/lemonade)
- **Flat Fee Model**: Lemonade takes a flat fee from premiums to run the business, rather than profiting from denying claims. This aligns the company with its customers.
- **First-Mover in Autonomous Car Insurance**: Launched a dedicated product for self-driving cars, pricing risk at ~50% of human-driven rates, positioning them for the future of mobility. [lemonade.com](https://www.lemonade.com/investor)

## Strategic Focus
- **Profitability**: The company is focused on reaching positive Adjusted EBITDA by Q4 2026, having already achieved positive adjusted free cash flow. [lemonade.com](https://www.lemonade.com/investor)
- **Product Expansion**: Continuing to launch new, innovative products (e.g., Autonomous Car insurance) and bundling existing ones (renters, car, pet, life) to increase customer lifetime value.
- **International Growth**: Expanding across the US and EU, with a growing customer base and increasing in-force premiums.

## Why Work Here
- **Culture**: Described as a "fast paced, ever changing, zero politics meritocracy." The company values "smart creatives" with "positive energy" and a "passion for building products people love." Emphasis on business impact, self-motivation, and flexibility. [makers.lemonade.com](https://makers.lemonade.com/)
- **Remote/Hybrid Policy**: Offers a hybrid workspace (flexible time on-site) in New York and remote roles in the US. In-office roles available in Tel Aviv, Israel and Amsterdam, Netherlands. [builtin.com](https://builtin.com/company/lemonade)
- **Notable Perks**: Offers company equity, 401(K), generous parental leave, dental/health/vision insurance, job training + conferences, and free snacks/drinks. [builtin.com](https://builtin.com/company/lemonade)
- **Engineering Culture**: Strong emphasis on "makers" who "move fast and spend their time building stuff instead of endless meetings." Tech stack includes Ruby, SQL, Python, R, Snowflake, and MySQL. [builtin.com](https://builtin.com/company/lemonade)

## Sources
1. [lemonade.com](https://www.lemonade.com/)
2. [makers.lemonade.com](https://makers.lemonade.com/)
3. [lemonade.com/investor](https://www.lemonade.com/investor)
4. [builtin.com](https://builtin.com/company/lemonade)
5. [co.linkedin.com](https://co.linkedin.com/company/lemonade-inc-)

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