Lemonade Inc. (NYSE:LMND) Q2 2022 Earnings Conference Call August 9, 2022 8:00 AM ET Company Participants Yael Wissner-Levy - Head of Content and Communications Daniel Schreiber - Co-Founder, Chairman and Co-CEO Shai Wininger - Co-Founder, President, Co-CEO Tim Bixby - Chief Financial Officer Conference Call Participants Michael Phillips - Morgan Stanley Thomas McJoynt - KBW Jason Helfstein - Oppenheimer Andrew Kligerman - Credit Suisse Katie Sakys - Autonomous Research Operator Hello, everyone, and a warm ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 5 Crosby Street, 3rd Floor New York, New York 10013 (Address of principal executive offices) (Zip Code) (844) 733-8666 (Registrant's telephone number, including area code) N/A or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition ...

Financial Data and Key Metrics Changes - In force premium (IFP) stood at $419 million, reflecting a 66% year-over-year growth [7][23] - Adjusted EBITDA loss for the quarter was $57 million, compared to a loss of $41.3 million in Q1 2021 [7][28] - Revenue increased by 89% year-over-year to $44 million [25] - Gross loss ratio was reported at 90%, an improvement from 96% in the previous quarter [25][28] Business Line Data and Key Metrics Changes - Premiums from single product customers grew at a rate of 61% year-over-year, while premiums for customers with two products grew at 140%, and those with three products jumped 390% [12] - The introduction of the mega bundle of insurance products (renters/home, life, pet, and car) in Illinois and Tennessee led to a 40% increase in bundle rates in Illinois [9][10] Market Data and Key Metrics Changes - The company reported a significant increase in annual dollar retention (ADR) in Illinois, reaching 90% during Q1 [10] - The majority of premium per customer growth was driven by a shift towards higher value homeowner and pet policies [24] Company Strategy and Development Direction - The strategy focuses on growing with customers through predictable life cycle events, which has shown to significantly boost both top and bottom lines [11] - The company aims to achieve a multiyear average loss ratio below 75%, with ongoing efforts to adjust rates in response to inflation [21][30] Management's Comments on Operating Environment and Future Outlook - Management acknowledged that inflation has impacted loss ratios, with claims adjusting quickly while rates take longer to align [20] - The company expects peak EBITDA losses in 2022, with a forecast for significant growth in in force premium by approximately 70% during the year [32][65] Other Important Information - The company is in the process of closing the Metromile acquisition, which is expected to enhance its product offerings and market presence [47][48] - Changes in the Board of Directors were announced, including the resignation of Caryn Seidman-Becker and Joel Cutler [13][15] Q&A Session Summary Question: Why has there been no or little insider buying despite the drop in market cap? - Management noted that the stock's decline reflects broader macroeconomic trends rather than company-specific issues, emphasizing their long-term conviction in Lemonade's prospects [33][34] Question: What indicators are tracked to analyze AI engine efficacy and how is inflation managed? - Management discussed the use of multiple metrics for AI efficacy and highlighted efforts to adjust rates in response to inflation, including automatic updates to policy assessments [36][38][41] Question: Will Lemonade release loss ratios on a byproduct basis? - Management indicated that while they understand the interest, they must balance transparency with competitive considerations, suggesting an Analyst Day may be held to share more information [43][44][45] Question: Update on the Metromile acquisition and integration? - Management confirmed that most preconditions for closing the Metromile deal have been met, with expectations for completion in Q2 [47][48] Question: Can you provide more color on the split between new and renewal customers? - Management stated that the focus has shifted towards expanding existing customers, with improvements in annual dollar retention noted [70] Question: What is the outlook for expenses post-Metromile acquisition? - Management expects a step-up in expenses upon consolidation but anticipates cost efficiencies as redundant costs are eliminated over time [93][96]

Lemonade Shareholder Letter Q1 2022 $419M In Force Premium (IFP) ↑ 66% YOY $279 Premium per Customer 1,504,197 Total Customers ↑ 37%YOY ↑ 22% YOY $252M ● $419M ● $133M ● Q120 90% Gross Loss Ratio ↓ 31% PTS YOY 121% 90% 72% ● 9 Q121 Q1 22 Q120 Q121 Q1 22 $96M Gross Earned Premium ↑ 71% YOY $96M $56M $31M Q122 Q120 Q121 2 Dear Shareholders, We're happy to report that the year kicked off with a strong first quarter. Notwithstanding the turbulent market forces and macroeconomic environment, both our top line an ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q Commission File Number: 001-39367 (Mark One) Lemonade, Inc. x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 (Exact Name of Registrant as Specified in Its Charter) (State or other jurisdiction of incorporation or organization) For the quarterly period ended March 31, 2022 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonade, Inc. (Exact name of Registrant as specified in its charter) (State or other jurisdiction of incorporation or ...

Financial Data and Key Metrics Changes - The company reported a 100% revenue growth in Q4 2021 compared to the prior year, with revenue reaching $41 million [6][28] - In-force premium grew 78% year-over-year to $380 million in Q4 2021 [26] - Premium per customer increased by 25% year-over-year to $266, driven by a mix shift towards higher-value policies [27] - The gross loss ratio for Q4 2021 was 96%, up from 73% in Q4 2020, primarily due to prior period adverse development [29][21] - Operating expenses, excluding loss and loss adjustment expenses, increased by 89% in Q4 2021 compared to the prior year [29] Business Line Data and Key Metrics Changes - Lemonade Car generated 3x the sales compared to Lemonade Pet during its initial launch period [17] - The majority of Lemonade Car customers are bundling with at least one other Lemonade policy, indicating strong cross-selling dynamics [18] - The company is seeing improvements in loss ratios for newer product lines, including pet and home insurance, although overall loss ratios have increased due to growth in these lines [23] Market Data and Key Metrics Changes - The company has diversified its product offerings, now including pet, life, and car insurance, which has contributed to a more balanced risk profile [10][12] - The shift in business mix has resulted in U.S.-based renters comprising less than half of the book, down from about two-thirds a year ago [22] Company Strategy and Development Direction - The company aims to leverage technology to lower expense ratios and improve loss ratios through automation and machine learning [10][15] - The strategy focuses on engaging customers early and providing a seamless experience, with plans to expand product offerings and improve customer retention [9][10] - The acquisition of Metromile is expected to enhance Lemonade's capabilities and accelerate growth in the car insurance segment [20][92] Management's Comments on Operating Environment and Future Outlook - Management anticipates 2022 to be a peak loss year, with expectations for EBITDA improvement in subsequent years [11][34] - The company remains optimistic about its cash position, with approximately $1.1 billion in cash and investments, which will support ongoing growth initiatives [31][42] - Management acknowledges the competitive landscape but believes that their multi-product, technology-first approach provides a strategic advantage [16][12] Other Important Information - The company is focused on integrating Metromile's teams and technology to enhance its product offerings and operational efficiency [20][93] - The company expects to close the Metromile acquisition in Q2 2022, which will further bolster its market position [20][43] Q&A Session Summary Question: Insider buying stock and company buybacks - Management noted that market volatility affects stock prices and emphasized a focus on long-term value creation rather than short-term share price fluctuations [36][38] Question: Sustaining rapid growth with high cash burn - Management highlighted a strong cash position and indicated that heavy investments in foundational products are nearing completion, expecting losses to decline in the coming years [40][42] Question: Timeline for Metromile deal closure and Lemonade Car availability - The Metromile deal is expected to close in Q2 2022, with plans to expand Lemonade Car availability across the U.S. within a year [43][44] Question: Proving technology advantage amid rising OpEx - Management acknowledged the challenge of demonstrating immediate benefits from technology investments but expressed confidence in long-term efficiency gains [45][46] Question: Long-term vision for Lemonade Car and loss ratio expectations - Management indicated that Lemonade Car will utilize telematics for precise pricing, with expectations for competitive loss ratios over time [57][68] Question: Impact of loss ratio on 2022 guidance - Management explained that the increase in loss ratio is due to a mix shift and prior adverse developments, but they expect improvements in loss ratios for newer products [89][90] Question: Growth guidance for in-force premiums - Management clarified that the growth rate is expected to be around 70% for 2022, influenced by the integration of Metromile [94][96]

Lemonade Shareholder Letter Q4 2021 $380M In Force Premium (IFP) ↑ 78% YOY $266 1,427,481 Total Customers ↑ 43% YOY ● Premium per Customer ↑ 25% YOY $213M ● $114M ● Q4 20 Q4 21 Q4 19 96% Gross Loss Ratio ↑ 23% PTS YOY 96% 73% 73% $89M Gross Earned Premium ↑ 79% YOY $89M $50M $26M Q4 19 Q4 20 Q4 21 $380M Q419 Q4 20 Q4 21 2 Dear Shareholders, 2021 was a very productive year for us, and we ended it materially larger, more diversified, and strategically stronger than ever. The year kicked off with a substantial ...

Lemonade, Inc. (NYSE:LMND) Q3 2021 Earnings Conference Call November 9, 2021 8:00 AM ET Company Participants Daniel Schreiber – CEO Shai Wininger – CTO Timothy Bixby – Chief Financial Officer Yael Wissner – VP Communications at Lemonade Conference Call Participants Michael Philips – Morgan Stanley Tracy Ben Gig-E – Barclays Jason Helfstein – Oppenheimer Andrew Plagerman – Credit Suisse Mike Zielinski – Wolfe Research Josh Shanker – Bank of America Christopher Martin – KBW Operator Good day, and welcome to t ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Lemonade, Inc. For the quarterly period ended September 30, 2021 (Exact Name of Registrant as Specified in Its Charter) or (State or other jurisdiction of incorporation or organization) 5 Crosby Street, 3rd Floor New York, New York 10013 Delaware 32-0469673 (I.R.S. Employer Identification No.) TRANSITION REPORT PURSUANT TO SECTIO ...