📄 What This Document Is 🧭

This document is a Proxy Statement (a DEF 14A filing). Think of it as a detailed instruction manual for the company's most important annual meeting—the Annual Meeting of Stockholders. 📚

Its purpose is not to provide quarterly financial results, but rather to inform you, the shareholder, exactly what votes you are being asked to cast on behalf of the company’s leadership, board structure, and internal policies. If you hold Lemonade stock, this is the document you need to know to exercise your voting rights.

👉 Key Takeaway: This filing is about corporate governance (how the company is run), not about day-to-day business results.

🏢 What Lemonade Does 🛡️

Lemonade, Inc. is an insurance technology company. 💻 In simple terms, they are revolutionizing traditional insurance models by leveraging technology and making the process of buying and claiming insurance smoother and more customer-friendly.

The company’s operations involve multiple units, including Lemonade Insurance Company, Lemonade Insurance Agency LLC, and Metromile, Inc. 🚗 This structure shows that they operate across different aspects of the insurance lifecycle, from the technology platform to the actual insurance underwriting and distribution.

👉 Why it matters: Being an "Insurtech" company means Lemonade’s success relies not just on predicting losses, but on developing smart, scalable technology to manage risk and customer experience.

📅 Annual Meeting Details 🗓️

Lemonade has set its Annual Meeting of Stockholders for Wednesday, June 3, 2026. 🗓️ This year, the meeting will be held entirely virtually via live webcast, offering flexible access for shareholders globally.

The company informs shareholders that they can attend the meeting and submit questions by visiting www.virtualshareholdermeeting.com/LMND2026.

The official Record Date—the date used to determine who is entitled to vote—is the close of business on April 9, 2026. As of that date, there were 76,818,039 shares of common stock outstanding and entitled to vote.

👉 Action Item: Shareholders are strongly urged to vote their shares promptly through the Internet, by phone, or by mail to ensure a quorum (enough votes to conduct business) and save the company the expense of further voting appeals.

🗳️ What You Are Voting On 📜

The proxy statement outlines four specific proposals that stockholders will be asked to vote on at the Annual Meeting. The Board of Directors recommends voting For all of them.

1. Election of Directors: Electing Michael Eisenberg and Debra Schwartz as Class III Directors to serve until the 2029 Annual Meeting (and beyond).
2. Ratification of Auditor: Ratifying the appointment of Ernst & Young LLP as the independent registered public accounting firm for the fiscal year ending December 31, 2026.
3. NEO Compensation: Approving, on an advisory (non-binding) basis, the compensation for the named executive officers (NEOs).
4. Other Business: Transacting any other proper business that may come before the meeting.

👉 Non-Binding Vote: It is crucial to note that the compensation vote is advisory and not legally binding, but it guides the Board in setting pay policies.

🏛️ Board Governance & Structure 🧱

The Board of Directors is the governing body, currently composed of eight members: Daniel Schreiber, Shai Wininger, Michael Eisenberg, Dr. Samer Haj-Yehia, Debra Schwartz, Maria Angelidis-Smith, Geoff Seeley, and Prashant Ratanchandani.

The board structure is designed to protect shareholder interests by dividing directors into three classes with staggered, three-year terms.

• The Challenge of Staggering: This structure means that not all directors are up for re-election at the same time. While this is common, the filing notes that this structure "may delay or prevent a change of our management or a change in control of our Company."
• Independence: The Board has determined that Michael Eisenberg, Dr. Samer Haj-Yehia, Debra Schwartz, Maria Angelidis-Smith, Geoff Seeley, and Prashant Ratanchandani qualify as "independent" directors under NYSE rules. However, the co-founders, Daniel Schreiber and Shai Wininger, are noted as not independent.
• Oversight: The Board has ultimate responsibility for overseeing risk management. They mandate that standing committees (like the Audit Committee) report regularly on the risks inherent in their areas of oversight.

🏆 Board Committees and Responsibilities 🤝

The Board operates through three key standing committees, each with defined responsibilities to ensure proper oversight of the company.

• 🔎 Audit Committee: (Members: Dr. Samer Haj-Yehia - Chair, Debra Schwartz, Prashant Ratanchandani)
  • What it does: This committee is responsible for the integrity of the financial statements. They oversee the independent accounting firm, review financial results, monitor internal controls, and approve related person transactions.
  • Special Status: The Board has affirmed that Dr. Haj-Yehia and Ms. Schwartz qualify as "audit committee financial experts."
• 💰 Compensation Committee: (Members: Michael Eisenberg - Chair, Maria Angelidis-Smith, Geoff Seeley)
  • What it does: This committee assesses and recommends compensation for NEOs and directors. They review the "Compensation Discussion and Analysis" (CD&A) and determined that a compensation consulting firm, Aon Human Capital Solutions (Aon HCS), assisted in this process.
• ⭐ Nominating and Corporate Governance Committee: (Members: Debra Schwartz - Chair, Michael Eisenberg, Maria Angelidis-Smith)
  • What it does: This committee is responsible for the company’s leadership pipeline. Their duties include identifying qualified candidates for directors, developing Corporate Governance Guidelines, and overseeing the annual evaluation of the Board.

💰 Executive Compensation Overview 💸

The Compensation Discussion and Analysis (CD&A) provides an overview and analysis of the compensation for the company’s Named Executive Officers (NEOs) for fiscal 2025. 📊

The NEOs identified are:

• Daniel Schreiber, Co-Founder and Chief Executive Officer
• Shai Wininger, Co-Founder and President
• Tim Bixby, Chief Financial Officer and Treasurer
• Adina Eckstein, Chief Operating Officer
• John Peters, Chief Insurance Officer
• Maya Prosor, Chief Business Officer

👉 Analyst Insight: The fact that the Compensation Committee engaged Aon HCS—a third-party compensation consultant—is standard best practice. It gives the Board credibility when deciding pay packages and signals they are benchmarking Lemonade's compensation against industry peers.

🛡️ Governance, Ethics, and Risk Policies ⚖️

The proxy statement dedicates significant space to its ethical and risk management policies, which is highly important for institutional investors. 📖

• Code of Ethics: The company maintains a written Code of Business Conduct and Ethics, applicable to all directors, officers, and employees.
• Insider Trading Policy: A formal policy is in place to govern the purchase, sale, and disposition of Lemonade securities by insiders. This policy specifically prohibits certain high-risk trading activities, such as short sales or pledging Company securities as collateral.
• Director Attendance: During the fiscal year ended December 31, 2025, there were five meetings of the Board of Directors. Each director was required to attend at least 75% of the aggregate meetings for the year.
• Risk Oversight: The Board views risk assessment as integral to its management. The Audit Committee is specifically responsible for monitoring financial, accounting, and cybersecurity risks. The Compensation Committee is responsible for assessing if any pay structure might encourage "excessive risk-taking."

📧 Getting Involved and Contact Info ☎️

If you have questions about these materials or want to learn more about the company, several resources are provided. 🌐

• Website/Investment Relations: You can visit the investor relations page at investor.lemonade.com.
• General Inquiries: Any general communications relating to corporate governance or long-term strategy should be addressed to the Secretary at 5 Crosby St. 3rd Floor, New York, New York 10013.
• Committee Contacts: Communications to specific committees (Audit, Nominating, or Compensation) can be forwarded to the Secretary.

🧠 The Analogy

Voting on a proxy statement is like being a Boardroom Judge for your own company. 🧑‍⚖️ You aren't making the day-to-day decisions (that's the CEO's job); instead, you are confirming if the judges (the Board) are independent, if the rules (the Governance Guidelines) are fair, and if the referees (the Audit Committee) are properly reviewing the scorebooks (the financials). You are voting on the system, not the score itself.

🧩 Final Takeaway

This proxy statement confirms Lemonade's commitment to strong governance by detailing its Board structure, committee roles, and ethical policies. Shareholders must pay attention to the voting procedures and dates (especially the Record Date of April 9, 2026) to ensure their rights are protected.