Serverless Craic Ep73 Liberty Mutual’s Cloud Journey to Serverless

Serverless Craic from The Serverless Edge

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In this episode Dave Anderson, Mark McCann, and Michael O’Reilly revisit their time at Liberty Mutual, exploring how one of the world’s largest insurers transformed from legacy systems and SOA to cloud-native architectures and serverless-first strategies.
Discover how Wardley Mapping, empowered engineering teams, and a strong cultural foundation enabled Liberty Mutual to modernise at scale and deliver business value faster.
We cover:
Moving from mainframes and monoliths to microservices and serverless
Building agile, product-led teams that own security, testing, and operations
Using Wardley Mapping to make strategic technology bets
Lessons on cloud adoption, change management, and leadership in a Fortune 100 enterprise
👉 If you’re a CTO, software architect, or engineering leader, this case study is packed with insights on modernisation and enterprise cloud transformation.
⏱️ Chapter Markers
0:00 – Introduction
0:34 – Liberty Mutual in Belfast: tackling hard problems
2:21 – Strategic mindset of a mutual insurance company
3:49 – Early SOA systems and first encounters with cloud
4:49 – Microservices before it was mainstream
6:14 – Enter serverless: below the line vs above the line
8:38 – Technology manifesto and cultural change
10:25 – Learning from world-class infrastructure engineers
13:53 – Wardley Mapping and spotting key enablers
16:08 – CDK, BDD, and shifting left
18:20 – Security, threat modelling, and shifting responsibilities
19:58 – Product thinking and “next best action”
21:31 – Working with auditors and external stakeholders
22:18 – Upskilling, conferences, and internal evangelism
24:08 – Business impact and scaling during COVID
25:39 – Change management: it takes a village
26:45 – External evangelism and organisational support
27:22 – Next episode teaser: Problem Prevention Culture
📚 Resources & Links
🌐 The Serverless Edge https://theserverlessedge.com
– Thought leadership on modern cloud
🎧 Podcast on Spotify
🎥 More episodes on YouTube
📖 The Value Flywheel Effect – by David Anderson, Mark McCann & Michael O’Reilly https://thevalueflywheeleffect.com

Serverless Craic from The Serverless Edge
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