Migrating from Monolith to Modern SaaS: Untangling 40 Years of Legacy

Abstract

What does it take to successfully modernize and migrate a mission-critical line of business running on a 40-year-old monolith to a more modern SaaS? In this talk, I'll share my journey of leading a large media organization to evolve a deeply embedded legacy system into a modern, service-oriented SaaS platform. To be clear, this wasn't a clean-slate rewrite—it was a careful transformation that involved unpacking decades of tribal knowledge, understanding complex business rules, and reshaping existing workflows while creating new ones. Dealing with tight integrations with other parts of the systems in the organization, all the while maintaining business continuity for the different lines of business that still run on the monolith. No migration is complete without a successful decommissioning, yet it must be done without risking revenue and business as usual.

We'll explore how domain-driven design and systems thinking guided us through complex decision-making, from identifying bounded contexts to decoupling capabilities. I'll discuss some of the architecture patterns that worked—and the ones that didn't—along with the lessons learned in stakeholder and team alignment, delivery, and balancing pragmatism with long-term goals. Whether you're staring down a legacy system or already in the trenches of migration, I'll share my hard-won insights to help you lead change with clarity and resilience.

Spoiler Alert: It's not just about the components, services, and architecture that will result in a successful modernization of systems. Systems are for people. Understanding the socio-technical challenges of an extensive modernization is the key.


Speaker

Indu Alagarsamy

Principal Engineer @NYTimes with 15 years of Software Development Experience

Indu enjoys designing distributed systems using event-driven architecture style and domain-driven design principles. She has over 15 years of software development experience working with various industries like healthcare, finance, biotech, and emergency services. She is currently a Principal Engineer at the New York Times. She is passionate about diversity and inclusiveness in the tech industry. When not working, she's an occasional rock climber, who loves to chill in sunny Southern California with her giant puppy.

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