Orchestrating Transformation

The case examines how a New York-based 10-year-old start-up, Lemonade Inc., successfully disrupted the insurance industry. Powered by artificial intelligence, Lemonade's mobile app replaced brokers and bureaucracy with bots and machine learning. The combination of simple product, no jargon, zero paperwork and an all-digital engagement allowed Lemonade to collapse costs, not at the expense of customer experience but to delight young customers with "instant everything" – from buying insurance in 90 seconds to getting claims paid in 3 seconds. Lemonade's notable milestones include surpassing $1 billion in in-force premiums in March 2025, a net loss ratio improvement from 97% in 2022 to 75% in 2025, and its first full year of positive adjusted free cash flow in 2024. Despite strong top-line growth, the company was yet to turn a profit, and its stock performance had been rocky. Lemonade posted a $202.2 million net loss in 2024, and its market capitalization stood at $4.2 billion in August 2025, significantly below its $9.8 billion peak in January 2021. Looking ahead, Lemonade aimed to increase in-force premiums tenfold, to $10 billion, by aggressively acquiring customers without significantly raising costs. As the stock regained market attention, bullish analysts highlighted ongoing progress toward profitability and improving loss ratios, whereas bearish analysts questioned the fundamentals behind the highly positive narrative presented by CEO Daniel Schreiber. A key question was whether the company could sustain its data- and AI-enabled competitive advantage or whether incumbents with deep pockets and growing technological investments would catch up. Against a backdrop of geopolitical tensions, uncertain macroeconomic conditions and increased competition, should institutional investors continue to invest in Lemonade or not?

In April 2021, Sava oban, the newly appointed EVP of Intertech, faces a perfect storm of Turkey's economic crisis and the global scramble for tech talent. This forces him to confront an operational meltdown at Intertech, the IT subsidiary of DenizBank. The massive talent exodus results in a 60 turnover rate, which threatens to derail critical projects as Intertech is now competing with both local firms and global giants hiring remotely during the Covid-19 pandemic. With traditional solutions proving insufficient, Sava proposes a radical strategy: pivoting from being a direct IT provider to an orchestrator of a platform ecosystem. The case challenges participants to map the practical steps necessary to build the ecosystem from the ground up by learning how to create trust with skeptical clients, internal teams and wary partners in the high-stakes fintech sector.

The case study examines the organizational transformation challenges faced by MedTech Diagnostics, an $850 million medical diagnostics company attempting to balance innovation speed with regulatory compliance and quality standards. CEO Patricia Chen must navigate the tension between traditional, reliability-focused operations and agile innovation pods, while facing a critical contract renewal worth $187 million that represents 22% of the company's revenue. The case illustrates the complexities of dual operating models in regulated industries. MedTech's traditional divisions generate $120M in EBITDA and are FDA-compliant but are declining at 8% annually. Innovation pods achieve 120% growth and high customer satisfaction but face higher post-market issues and lower FDA approval rates. Hybrid teams – intended as a compromise – satisfy neither approach, demonstrating the difficulties of organizational ambidexterity. Chen faces three strategic options: controlled evolution over 24 months, creating a separate subsidiary for innovation, or transforming into a platform company. Each option carries significant costs, risks, and uncertain outcomes. The case explores critical organizational design questions, including culture change, stakeholder management, resource allocation, regulatory navigation, and leadership alignment in transformation contexts. Key themes include managing organizational culture during transformation, balancing innovation with quality in regulated environments, addressing internal resistance and political dynamics, developing effective dual operating systems, and making high-stakes strategic decisions under uncertainty. The case is designed for classroom discussion on organizational change, innovation management, and strategic decision-making in complex operating environments.

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