Cofounder of Cucumber Ltd. on RSpec, Cucumber, and legacy systems with Matt Wynne

In this episode of the Distributed podcast, Jack Hannah sits down with Matt Wynne, staff software engineer at Mechanical Orchard and a longtime advocate for Agile and Behavior-Driven Development (BDD). Matt shares his journey from working with legacy systems to co-founding Cucumber Ltd., offering a firsthand look at how testing, pairing, and social programming create more effective teams.

Matt also discusses the challenges of modernizing outdated infrastructure, the role of ensemble programming in fostering collective code ownership, and why strong relationships are essential for high-functioning distributed teams.

Highlights:

• The power of social programming: how pairing and ensembling improve collaboration and knowledge-sharing
• The evolution of BDD and its impact on software development
• Strategies for handling legacy modernization projects with minimal disruption
• Why creating psychological safety leads to stronger remote teams and better engineering outcomes
• The future of automation, AI, and the next wave of innovation

In this episode, we cover:

(00:00) - Kicking things off with Matt Wynne

(00:13) - From COBOL to modernization: Lessons in legacy systems

(05:05) - The origins of Cucumber and BDD

(07:44) - Pairing, ensembling, and the power of social programming

(11:38) - Extracting knowledge from aging codebases

(14:07) - Building tools for faster legacy system migrations

(21:01) - Creating psychological safety in engineering teams

(29:19) - Selling change: How to introduce new development practices

(33:02) - Remote work and the importance of human connection

References

Working Effectively with Legacy Code by Michael Feathers

Agile Coaching by Rachel Davies and Liz Sedley

Where to connect further:

Connect with Matt Wynne on LinkedIn and his Website

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Want to hear more? Check out distributed.fm

Connect with Jack Hannah