CTO coach Joel Chippindale joins Robby to share what he's learned over two decades of building and leading software teams. Joel argues that maintainability has less to do with “clean code” and more to do with how teams communicate, prioritize, and make progress visible. Drawing on his time at Unmade and his current coaching practice, Joel outlines practical ways teams can build trust, navigate brittle systems, and stop letting tech...

Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage

Melanie Sumner, Product Accessibility Lead for Design Systems at HashiCorp, joins Robby to talk about what it takes to scale accessibility across legacy products—and how aligning design and engineering processes creates lasting change. Melanie shares her work making Ember.js more accessible, her team’s philosophy behind their design system, and why she tr...

In this episode of Maintainable, Robby speaks with Joe Masilotti, an independent consultant who helps Rails teams ship mobile apps using Hotwire Native.

Joe shares his perspective on what makes software maintainable—especially for consultants who need to onboard quickly. He explains why setup scripts often add unnecessary complexity, and how he evaluates a project’s maintainability by how quickly he can go from clone to coding.

Robby...

Freedom Dumlao (CTO at Vestmark) joins Robby to explore what it means to maintain software at scale—and why teams sometimes need to unlearn the hype.

With two decades of experience supporting financial systems, Freedom shares how his team manages a Java monolith that oversees $1.6 trillion in assets. But what’s most surprising? His story of how a team working on 70+ microservices rebuilt their platform as a single Ruby on Rails mono...

Mercedes Bernard, Staff Software Engineer at Kit, joins Robby to talk about what it really means to write code that lasts—and who it should be written for.

In this episode of Maintainable, Mercedes shares a thoughtful and practical perspective on working with legacy codebases, managing technical debt, and creating a team culture that values maintainability without fear or shame. Her guiding principle? Well-maintained software is fri...

Evan Phoenix (@evanphx), CEO of Miren, joins Robby to explore the subtle but powerful difference between writing code that works and writing code that explains itself. They discuss the role of clarity in maintainable systems, why splitting a monolith can backfire, and what developers can learn from artists and tradespeople alike.

Episode Highlights

[00:01:30] What Makes Software Maintainable?
Evan defines maintainability as h...

Software isn’t always about rapid iteration. Sometimes, the real challenge lies in carefully assessing the existing environment. Chris Salvato, a Senior Staff Engineer at Shopify, believes that spending time in the “problem space” is vital for any long-lived application. Rather than diving immediately into controllers and tests, he begins by talking to everyone who interacts with the code—engineers, product owners, even directors w...

Heimir Thor Sverrisson joins Robby to discuss the importance of software architecture in long-term maintainability. With over four decades in the industry, Heimir has witnessed firsthand how poor architectural decisions can set teams up for failure. He shares his experiences mentoring engineers, tackling technical debt, and solving large-scale performance problems—including one bank’s misguided attempt to fix system slowness by sim...

Not every messy piece of code needs a refactor. Noémi Ványi, Senior Software Engineer at Xata, joins Robby to discuss how to develop the intuition to know when refactoring is truly necessary and when it’s just unnecessary churn. She shares her approach to balancing pragmatism and maintainability, how product teams and developers can work better together, and why developer autonomy is key to sustainable software.

Drawing from her exp...

How much can legacy code tell us beyond just functionality? Julia López, Senior Software Engineer at Harvest, believes that even small details—such as white spaces, variable names, and formatting choices—can reveal a system’s history.

In this episode, Julia and Robby discuss the importance of refactoring and how a strong engineering culture can make or break a team's ability to maintain and improve software over time. Julia shares h...

Episode Overview

Marty Haught joins Robby to discuss the sustainability of open-source projects, the challenges of maintaining RubyGems, and why the metaphor of technical debt may not fully capture how software ages. Instead, he suggests thinking of it as drift—the natural misalignment of software with its evolving purpose over time.

They also dig into security challenges in package management, including how Ruby Central wor...

Mike Bowers, Chief Architect at FairCom, has spent decades navigating the evolution of database technology. In this conversation, he and Robby explore the challenges of maintaining a 40+ year-old codebase, balancing legacy constraints with forward-thinking design, and the realities of technical debt.

Mike shares how FairCom transitioned from ISAM-based databases to modern JSON-driven APIs, the trade-offs between strict schemas and f...

Join Robby as he chats with Lorna Mitchell, open source advocate and technical writer, about the art of creating documentation that doesn’t gather dust. Lorna shares her experiences as a maintainer of the open source project RST2PDF, the value of API governance, and how documentation bridges gaps in developer experience.

Highlights:

• What Makes Software Maintainable: Characteristics like great documentation, automated tes...

Episode Summary

In this episode of Maintainable, Robby sits down with Carola Lilienthal, Software Architect and Managing Director at WPS. Together, they explore the intersection of cognitive science and software architecture, strategies for tackling technical debt, and why simplicity, modularity, and domain knowledge are crucial for maintainability.

Carola shares her approach to improving legacy systems, fostering domain-dri...

Topics Discussed

• The importance of changeability as a core characteristic of well-maintained software.
• How GitHub has approached accessibility as a business and legal imperative.
• The evolution of GitHub’s frontend system, spanning over 2,000 pages, and the concept of "frontend vintages."
• Primer: GitHub’s design system and the paradox of its success—consistency vs. changeability.
• The disproportionate maintenance costs of fro...

Austin Story, Senior Engineering Director at Doximity, joins Robby to explore the intricacies of building maintainable systems, fostering team accountability, and enabling faster iteration without sacrificing quality. Austin shares how his team approached migrating from a monolithic GraphQL architecture to a federated model, why simplicity matters for long-term success, and how guiding principles like YAGNI influence his decision-m...

Topics Covered

Characteristics of Maintainable Software
Dan emphasizes the importance of internal consistency in codebases, automated tests, and proper documentation to preserve decision-making context.

• [00:05:32] Internal consistency: Why it matters.
• [00:08:09] Lessons from maintaining legacy codebases.

Working with Legacy Systems
Dan shares stories of upgrading ORM frameworks, introducing caching systems, and transiti...

In this episode of Maintainable, Robby speaks with Tom Johnson, Co-Founder and CEO of Multiplayer. Tom shares his perspectives on the evolving landscape of distributed systems, the challenges of maintaining legacy software, and how innovative tools are transforming the way teams collaborate.

Topics Discussed

• Characteristics of well-maintained software, from system-level documentation to effective workflows.
• The importance...

In this episode of Maintainable, Robby speaks with Gulcin Yildirim Jelinek, a Staff Database Engineer at Xata. Joining from Prague, Czech Republic, Gulcin discusses her experiences working with legacy databases, the evolution of Postgres, and her passion for building accessible tech communities.

Gulcin shares practical insights into modern database management, including the rise of automation tools like YAML and Pgroll, as well as h...