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Matt also discusses the challenges of modernizing outdated infrastructure, the role of ensemble programming in fostering collective code ownership, and why strong relationships are essential for high-functioning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

Follow Tuple

Want to hear more? Check out distributed.fm

Connect with Jack Hannah

In this latest episode of the Distributed podcast, host Jack Hannah interviews Colin Sidoti, Clerk Cofounder & CEO, to discuss what’s allowed them to grow so rapidly and deliver such an incredible developer experience for users. Colin reflects on how limited process fosters growth and allows his team of engineers and designers to excel.

Colin also provides insight into the nontraditional ways Clerk streamlines work, including their hiring practices and unique team dynamics.

Highlights:

• Understanding how Clerk has grown through a highly autonomous team culture
• Colin's insights on the importance of fluid communication in a distributed team
• The pivotal role the DX Guide plays in creating an amazing product
• Empowering teams by trusting their instincts and encouraging adaptability

In this episode, we cover:

(00:00) – Kicking things off with Colin Sidoti

(03:26) – Product development at Clerk

(08:29) – Remote work dynamics: synchronizing across time zones

(12:54) – Importance of fluid communication: using Tuple for efficient syncs

(14:44) – The role of DX Guide: maintaining high standards in product experience

(22:28) – Building a culture of customer-centric development

(17:40) – Evolving product offerings: from auth to billing and beyond

(25:56) – Hiring for passion: finding team members who care deeply

(31:55) – Simplifying user onboarding: eliminating friction for developers

(33:34) – Impact of removing friction: boosting adoption with minimal steps

Where to connect further:

Connect with Colin Sidoti on X and Clerk

Follow Tuple

Want to hear more? Check out distributed.fm

Connect with Jack Hannah

Engineering teams whose work leaves an impact thrive on trust, collaboration, and the appropriate technical practices.

In this episode of the Distributed podcast, host Jack Hannah sits down with Ryan Bergman, Principal Engineer at John Deere, to explore the impact of Extreme Programming (XP) and agile practices on software development. Ryan shares how XP principles helped stabilize a struggling startup, why pair programming is essential for team cohesion, and how behavior-driven development (BDD) builds confidence in large-scale systems.

They also discuss the challenges of remote collaboration, lessons from scaling software at John Deere, and what it takes to align distributed teams around a shared technical vision.

Highlights:

• Rescuing a struggling startup by embracing Extreme Programming to improve collaboration, code quality, and technical execution
• Strengthening engineering teams with pair programming and the right balance of structure and flexibility
• Managing large-scale software development at John Deere
• Building trust across distributed teams through clear communication, shared technical vision, and an emphasis on psychological safety
• Using Behavior-Driven Development (BDD) to create reliable, well-tested systems that give teams confidence in their software

In this episode, we cover:

(00:00) – Kicking Things Off with Ryan Bergman

(01:10) – Ryan’s Journey: From Graphic Arts to Engineering

(03:59) – Discovering XP: How Extreme Programming Saved a Startup

(08:09) – Pair Programming and Agile Coaching: Rebuilding from the Ground Up

(14:14) – Navigating Large-Scale Systems at John Deere

(16:22) – The Power of Trust: Autonomy, Collaboration, and ‘Vampire Rules’

(21:37) – Building Strong Engineering Teams Through Open Knowledge Sharing

(26:49) – Pair Programming Pitfalls: Fixing What Doesn’t Work

(37:11) – Behavior-Driven Development: Creating Confidence in Complex Systems

Where to connect further:

Connect with Ryan Bergman on LinkedIn and check out John Deere

Follow Tuple

Want to hear more? Check out distributed.fm

Connect with Jack Hannah