Slide 1: Investor Presentation
Investor Presentation Updated as of June 30, 2026
Slide 2: Forward-Looking Statements
Forward-Looking Statements This presentation contains statements, estimates or projections that constitute “forward-looking statements” as defined under U.S. federal securities laws. Statements contained in this presentation that do not relate to matters of historical fact should be considered forwa
Slide 3: The world spends more money on insurance than on advertising, aerospace, agriculture...
The world spends more money on insurance than on advertising, aerospace, agriculture, artificial intelligence, automotive, cloud- computing, cybersecurity, defense, education, electronics, entertainment, fashion & apparel, food & beverages, oil & gas, renewable energy, pharma, semiconductors, shippi
Slide 4: Insurance is a prize worth fighting for
The world spends more money on insurance than on advertising, aerospace, agriculture, artificial intelligence, automotive, cloud- computing, cybersecurity, defense, In short, insurance is a prize education, electronics, entertainment, worth fighting for fashion & apparel, food & beverages, oil & gas
Slide 5: Insurance companies are in the business of pricing risk and serving customers
Insurance companies are in the business of pricing risk and serving customers. Nothing does that more accurately and efficiently than AI.
Slide 6: Legacy insurance companies are byproducts of the Industrial Revolution
Legacy insurance companies are byproducts of the Industrial Revolution. They struggle to deliver the quality, speed, and ease of use that customers expect in 2026.
Slide 7: Lemonade is the only full-stack, multi-line insurance company built on AI
Lemonade is the only full-stack, multi-line insurance company built on AI, enabling us to price risk, collapse costs, and delight customers like never before.
Slide 8: AI enables price leadership, growth and profit at scale
By driving accurate pricing and collapsing costs, AI enables price leadership, which in turn powers industry-leading growth and massive profit at scale PRICE RISK AI PRICE GROWTH PROFIT LEADER LEADER LEADER LEADER COLLAPSE COSTS
Slide 9: Excellent underwriting performance: rapid data feedback loops enhance our AI models
price risk Excellent underwriting performance: Rapid data feedback loops enhance our AI models IFP vs Trailing Twelve Months Gross Loss Ratio 88% $1,434 85% 83% 79% 77% Gross Loss Ratio 73% 73% improvement alongside 70% significant IFP growth 67% yields >100% $719 64% compounded Quarterly Gross Prof
Slide 10: AI powers sustained efficiency improvement
Collapse cost AI powers sustained efficiency improvement ... IFP per employee grew ~3x in 4 years $1.07M >50% claims automation yields 5% overall LAE Ratio*; many at- scale incumbents are at ~9% IFP more than doubled since Q2 2023, while headcount is materially unchanged $0.40M Q2 22 Q2 26 *Cost of
Slide 11: ... to the delight of our customers
Delight ... to the delight of our customers >50% of claims Purchase a policy paid instantly in <90 seconds RATED 4.9/5 IN THE APP STORE Top insurance products as rated by MarketWatch, Forbes, and our own customers Source: MarketWatch | Forbes
Slide 12: We win high-LTV customers >10 years before incumbents
G ROW T H We win high-LTV customers >10 years before incumbents… site po ge com ers er a s s pe to m ro ce c us ac n ge ura e a ins rag cale ve -s A at of 45 Life r 35 nde 35 u 0% >5 Car Pet Renters Condo Homeowners Source: Morning Consult
Slide 13: As our cohorts mature, we expect to dramatically expand wallet share
GROWTH ... As our cohorts mature and spend more on insurance, we expect to dramatically expand wallet share >$15K >$10K $5K $138 $433 LMND LMND US Top High Net 2018 Q2 2026 Average LMND Worth Source: Bankrate Note: figures on page represent annual premium per customer. customer
Slide 14: Lemonade has become the preferred brand among the next generation of insurance buyers
GROWTH Lemonade has become the preferred brand among the next generation of insurance buyers Lemonade Market Share in U.S. 8% 1 6% preferred brand for 22-40 year olds 4% 2 1 2% most searched most searched in renters in pet 0% 2016 2018 2020 2022 2024 Lemonade renters Lemonade pet Source: Lemonade ma
Slide 15: Price leadership and the best experience have powered 11 consecutive quarters of IFP growth acceleration
GROWTH Price leadership and the best experience have powered 11 consecutive quarters of IFP growth acceleration YoY IFP growth rate >3M 29.2% 30.2% 31.0% 32.3% 32.4% Customers 26.3% 26.9% 23.7% >$1.4B 21.6% 22.2% 19.5% IFP 18.0% Q3 23 Q4 23 Q1 24 Q2 24 Q3 24 Q4 24 Q1 25 Q2 25 Q3 25 Q4 25 Q1 26 Q2 26
Slide 16: Growth acceleration and operating leverage are driving Lemonade to profitability
Profit Growth acceleration coupled with sustained operating leverage is driving Lemonade to profitability Adj. FCF as leading indicator of profitability; Adj. EBITDA and Net Income to follow 11 consecutive >100% multi quarters IFP growth year Gross acceleration Profit compounded growth rate $0 Signi
Slide 17: What's next: we'll grow IFP from $1b to $10b
What’s next: we’ll grow IFP from $1b to $10b by doing exactly what we’ve been doing 11 consecutive Qs acceleration Underwriting excellence 30%+ IFP growth Sustainable industry-leading Gross Profit growth ss e n si u b e th w ro G Adj. Free Cash Flow positive Scale the operation Adj. EBITDA breakeven
Slide 18: We expect car and bundling to become powerful growth engines
We expect car and bundling to become powerful growth engines in our next phase
Slide 19: Insurance is a prize worth fighting for
Insurance is a prize worth fighting for. Insurers are in the business of pricing risk and serving customers. Nothing does that more accurately and effectively than AI. No one is wielding AI in insurance like Lemonade.
Slide 20: Thank you.
Thank you. Lemonade