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 technical debt conversations get lost in translation. Episode Highlig...
Jul 01, 2025•57 min•Ep. 209
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 treats accessibility like any other technical concern. From the pitfalls o...
Jun 10, 2025•50 min•Ep. 208
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 and Joe also discuss how hybrid mobile development can offer...
May 20, 2025•56 min•Ep. 207
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 monolith—and started shipping faster than ever before. Episode High...
Apr 22, 2025•1 hr 3 min•Ep. 206
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 friendly software—code that is understandable and approachable, ...
Apr 08, 2025•49 min•Ep. 205
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 how easily a newcomer can make a change with minimal context. [00:02...
Apr 01, 2025•1 hr 9 min•Ep. 204
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 who oversee strategy. This approach reveals hidden friction poin...
Mar 25, 2025•47 min•Ep. 203
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 simply adding more CPUs. Heimir also discusses his work at MojoTech ...
Mar 18, 2025•41 min•Ep. 202
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 experience working on both open-source and closed-source projects...
Mar 11, 2025•42 min•Ep. 201
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 her experience leading a multi-year overhaul of Harvest’s billin...
Feb 25, 2025•51 min•Ep. 200
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 worked with Trail of Bits to audit RubyGems. Marty also shares insights ...
Feb 18, 2025•53 min•Ep. 199
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 flexible document stores, and how software architecture plays a ...
Feb 11, 2025•45 min•Ep. 198
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 tests, and onboarding ease. Documentation's Role in Long-Lived Software: Why i...
Jan 28, 2025•43 min•Ep. 197
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-driven development, and introducing sustainable patterns into software de...
Jan 21, 2025•43 min•Ep. 196
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 frontend systems compared to backend systems. Using tools like Axe and keybo...
Jan 14, 2025•46 min•Ep. 195
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-making. Doximity is a leading digital platform for medical profess...
Dec 10, 2024•47 min•Ep. 194
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 transitioning to bug tracking tools. [00:09:52] Replacing custom ORM systems with Hib...
Dec 03, 2024•49 min•Ep. 193
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 of debugging tools tailored for distributed systems. Anecdotes about man...
Nov 26, 2024•43 min•Ep. 192
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 how extensions like pgvector are unlocking new possibilities f...
Nov 19, 2024•38 min•Ep. 191
Robby sits down with Justine Gehring , an AI Research Engineer at Moderne , to explore how AI tools are transforming code maintenance and scalability. They dive into the unique ways AI can support refactoring for massive and legacy codebases, from retrieval-augmented generation (RAG) to lossless semantic trees, and discuss how developers can benefit from AI-assisted planning and refactoring. Justine shares her background transitioning from academia to industry and reflects on the essential role ...
Nov 12, 2024•48 min•Ep. 190
As a product advocate at Nx , Katerina Skroumpelou combines her engineering skills with a knack for connecting with clients. In this episode, she shares how clear documentation, scalable architectures, and a collaborative culture can transform software development for the better. Key Takeaways [00:01:25] Katerina’s Background: Robby and Katerina discuss her career journey, starting in engineering and recently moving into product advocacy. [00:02:29] Characteristics of Well-Maintained Software: K...
Nov 05, 2024•37 min•Ep. 189
Welcome to another engaging episode of the Maintainable Software Podcast! In this episode, Robby sits down with Moriel Schottlender, Principal Software Engineer at the Wikimedia Foundation , to explore the complex journey of modernizing MediaWiki , the software behind Wikipedia . Moriel shares her insights on what it takes to keep an enormous monolithic codebase maintainable while supporting an ever-growing and diverse set of global users. She highlights the importance of modularization, ownersh...
Oct 22, 2024•46 min•Ep. 188
Welcome to another engaging episode of Maintainable! Robby sits down with Kate Holterhoff, Ph.D., a Senior Analyst at RedMonk and former front-end engineer, to explore the intricate world of software maintenance, documentation, and the future of developer roles. Kate brings her unique perspective from her time as a practitioner at a digital marketing agency, her academic background, and her current role in developer advocacy. Topics Explored [00:00:00] Introduction to Kate's Background : Robby a...
Oct 15, 2024•52 min•Ep. 187
Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing In this episode of Maintainable, Robby speaks with Alan Ridlehoover , Senior Engineering Manager at Cisco Meraki . Alan shares his perspective on building well-maintained software by focusing on behavior-centric testing, clear code ownership, and thoughtful technical decisions that stand the test of time. Alan discusses his experience working in both startup environments and large-scale engineering teams, including how he...
Oct 08, 2024•48 min•Ep. 186
In this episode of Maintainable , Robby speaks with April Wensel , Founder and Owner of Compassionate Coding . April shares her journey in the software industry and how she came to embrace compassion as a core value in coding and team dynamics. She explains why empathy is critical when working with legacy code, mentoring junior developers, and addressing technical debt. Episode Highlights [00:05:32] Introduction to Compassionate Coding: April discusses the mission behind Compassionate Coding and...
Oct 01, 2024•52 min•Ep. 185
In this episode of the Maintainable Software Podcast, Robby sits down with Saron Yitbarek , founder and CEO of DiscoLink , to explore the challenges of maintaining early-stage software while balancing multiple streams of income. Saron shares her journey from being a solo developer to hiring her first teammate and the lessons learned along the way about code maintainability and business logic. Episode Highlights [00:05:32] Introduction to Saron's Background: Robby and Saron discuss her startup, D...
Sep 24, 2024•41 min•Ep. 184
Introduction In this episode of Maintainable, Robby speaks with Lutz Hühnken , Head of Engineering Excellence at Upvest , about the transformative power of event-driven architecture in software development. Lutz brings his extensive experience to the table, discussing how breaking down complex systems into manageable modules and leveraging event-driven design can lead to more resilient and maintainable software. Topics Discussed [00:05:32] Introduction to Well-Maintained Software : Lutz shares h...
Sep 10, 2024•45 min•Ep. 183
In this episode of the Maintainable Software Podcast, Robby is joined by Noel Rappin , Staff Engineer at Chime Financial , and the mind behind the latest edition of the classic Programming Ruby book, affectionately known as the "Pickaxe." Noel delves into the intricate process of modernizing a legacy technical book and the lessons learned along the way. Episode Highlights [00:05:32] A Legacy Revisited : Noel Rappin reflects on the process of updating the Programming Ruby book, navigating the bal...
Sep 03, 2024•44 min•Ep. 182
In this episode of the Maintainable Software Podcast, Robby sits down with Cassidy Williams , Developer Advocate at GitHub, to explore the dynamic nature of a tech career, the delicate balance between clever code and maintainability, and the evolving trends in software development. Cassidy begins by discussing what makes software truly maintainable—starting with the ease of onboarding for new developers. She emphasizes the importance of clear documentation and warns against the pitfalls of writi...
Aug 27, 2024•43 min•Ep. 181
In this episode of the Maintainable Software Podcast, Robby speaks with Obie Fernandez , Chief Scientist at Olympia , about the integration of AI into modern software development. Obie shares his unique perspective on leveraging AI to enhance the maintainability and functionality of software applications, particularly in the Ruby on Rails ecosystem. Episode Highlights [00:01:00] Characteristics of Well-Maintained Software : Obie emphasizes the importance of test coverage and the role of Ruby in ...
Aug 20, 2024•44 min•Ep. 180
