At The Serverless Edge, we often reflect on the lessons learned from real-world enterprise cloud transformations. One of the most compelling stories comes from our time at Liberty Mutual, a Fortune 100 insurer with over a century of history.
In this post, we’ll share how Liberty Mutual navigated the shift from service-oriented architecture (SOA) and mainframes to cloud-native architectures and eventually a serverless-first strategy. This journey offers powerful lessons for any organisation seeking to modernise at scale.
A Fortune 100 Insurer with a Strategic Mindset
Liberty Mutual has always had a long-term perspective, thanks to its mutual structure. Unlike publicly traded companies driven by quarterly results, Liberty Mutual had the ability to make strategic technology bets.
The Belfast office in particular became a hub for solving difficult software problems. From early SOA implementations to large-scale enterprise systems, the teams gained invaluable experience modernising legacy platforms and experimenting with emerging technologies.
From SOA to Cloud Awareness
By the early 2010s, Liberty had delivered some of its largest systems using SOA and BPM. But the arrival of public cloud signalled a fundamental change.
We quickly realised that to fully leverage cloud, we would need to write software differently. This wasn’t just about lift-and-shift—it was about rethinking architecture, deployment, and ownership.
Microservices Before They Were Mainstream
In practice, we were already breaking down monoliths into finer-grained services before “microservices” became a mainstream term. That experience gave us a strong foundation when the industry began to shift towards cloud-native practices.
By 2014, when AWS Lambda launched, we were ready. Concepts like “above the line vs below the line” and “undifferentiated heavy lifting” resonated deeply, reinforcing our belief in serverless-first thinking.
Cultural Change and the Technology Manifesto
Transformation wasn’t just about technology. Culture played a central role.
In 2016, Liberty Mutual’s leadership published a technology manifesto, written in the style of an Amazon six-pager. This document codified principles such as:
- Cloud-native first
- Product-driven, cross-functional teams
- Build it, run it, own it
- Shift-left on testing and security
This manifesto became a north star for teams across the organisation.
Wardley Mapping as a Strategic Compass
One of the most powerful tools in the journey was Wardley Mapping. By mapping the value chain and tracking the evolution of technologies, we could:
- Identify inertia points and bottlenecks
- Delay premature custom development in anticipation of AWS services
- Adopt new enablers like AWS CDK as soon as they emerged
This situational awareness prevented wasted effort and kept us aligned with strategic outcomes.
Shifting Left: Security, Testing, and Ownership
Enterprise inertia often slows adoption of new paradigms. Security reviews, infrastructure provisioning, and testing cycles were all bottlenecks.
To address this, Liberty Mutual invested heavily in:
- Collaborative threat modelling to bring security into teams
- Behaviour-driven development (BDD) with tools like Cucumber
- Developer portals and pipelines that empowered teams to own infrastructure
This shift enabled faster, safer, and more autonomous delivery.
Empowered Teams and Product Thinking
As technical maturity grew, the focus shifted from “how do we deliver?” to “what should we deliver?”. Teams became increasingly product-led, aligning closely with business leaders to focus on next best actions that created real customer value.
Lessons Learned
The Liberty Mutual journey illustrates that true modernisation requires more than adopting new technologies. It demands:
- Leadership support and cultural change
- Strategic tools like Wardley Mapping to guide decisions
- Empowered, product-led teams
- A long-term commitment—modernisation is not a six-month project
As we often say: it takes a village. Sustainable enterprise transformation is a collective effort across technology, culture, and leadership.
Conclusion
Liberty Mutual’s transformation stands as a landmark case study in enterprise cloud adoption and serverless-first thinking. It shows that with the right culture, strategy, and leadership, even century-old enterprises can modernise at scale and thrive in the digital era.