Even-Keeled - A Software Development Podcast

How Our Dev Team Actually Ships With AI in Early 2026

jon@headway.io (Dan Diemer, Tim Gremore, Jon Kinney) — Thu, 19 Feb 2026 12:00:00 +0000

How does a dev agency actually use AI to ship production software? In this episode of Even-Keeled, the Headway development team pulls back the curtain on their real AI workflows, the tools they're using daily, and why experienced developers are writing the best code of their careers right now.

Jon Kinney (CTO), Tim Gremore, and Dan Diemer talk through how they're helping clients leverage AI, what happens when vibe-coded apps need to go to production, and why convention over configuration gives frameworks like Ruby on Rails and Elixir a serious edge in the age of agentic development.

SEGMENTS

00:00 - How we help clients leverage AI

03:30 - First AI deployment: a baseball coaching app 4:00 - Frontier models and secure data access

05:09 - Design systems and agentic workflows

06:00 - Figma MCP and filling the tooling gaps

10:02 - Why AI gives different answers every time

11:27 - What actually needs generative AI vs. traditional automation

13:01 - Software spikes and controlling the slop factor

16:01 - Why experienced devs are writing better code with AI

17:23 - Convention over configuration as an AI advantage

20:00 - Making vibe-coded apps production-ready

25:23 - How clean code feeds the AI feedback loop

27:10 - Dev tooling: Claude Code, TideWave, Beads, Pencil.dev

30:08 - Figma to code and design system challenges

32:40 - Claude Max plans, token limits, and pricing

38:00 - Building your AI cyberdeck

42:50 - "Code is cheap" and why taste matters now

45:30 - How AI is changing project estimation

TOPICS COVERED

How a product agency uses AI on real client projects
Why LLMs are non-deterministic and what that means for enterprise software
Claude Code, TideWave, Beads, Pencil.dev, and Open Code compared
Figma MCP and design system integration with agentic workflows
Ruby on Rails and Elixir as AI-friendly frameworks
Making vibe-coded apps enterprise-grade
Context windows, token efficiency, and the slop factor
How AI changes software estimation and project scoping

### ABOUT EVEN-KEELED

Even-Keeled is a podcast about building software in the age of AI. From design systems and agentic workflows to vibe-coded apps and more, the development leadership team at Headway shares what's working, what's not, and what they're learning on real client projects. No hype. Just how the work gets done. New episodes monthly.

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

07: System Architecture and Conway's Law

Mon, 20 May 2024 11:00:00 +0000

Dive into the intricate world of system architecture, focusing on Conway's Law and its impact on software development. Learn how organizational communication structures can shape the architecture of systems. The Headway team discusses the balance between creating independent teams for faster development and the potential pitfalls of unnecessary silos, especially for startups and smaller teams.

Listen to debates on the merits of microservices versus monolithic applications, with insights into how modern technologies like Elixir's flame pattern and serverless solutions like AWS Lambda can offer scalable and efficient solutions. They also discuss hosted environments, from on-premises setups to cloud-native solutions, and how new patterns and technologies make it easier for developers to build robust applications without deep DevOps expertise. This episode provides valuable perspectives and innovative approaches to system design and scalability. Tune in for a thought-provoking discussion that bridges theory and practical application in software architecture.

Discussion:

01:34 Diving into System Architecture and Deployment Evolution

02:20 Exploring Conway's Law in Software Development

04:04 The Challenges of Team Communication and Project Management

06:45 Efficiency in Small Teams: The Power of Three

09:04 Navigating Full Stack Development and Conway's Law

17:14 Innovative Approaches to Hosted Infrastructure Technology

27:32 Concluding Thoughts on Conway's Law and the Future of Software Development

Resources Mentioned:

Conway's Law and The Mythical Man-Month

Elixir and the Flame Pattern

Serverless and Hosted Environments

Full-Stack Development and LiveView

06: Design Systems in Action: Collaboration Between Designers and Developers

Thu, 16 May 2024 11:00:00 +0000

The Headway development team dives into the power of design systems and seamless designer-developer collaboration.

Learn about implementing design systems in various environments, automated design-to-code processes, and the crucial role of detailed design documentation.

Find out how tools like Tailwind and Storybook can enhance or complicate development. The team doesn't shy away from discussing the real-world implications of maintaining design systems and the delicate balance of collaboration required between designers and developers.

Discover how tools like Figma, Tailwind CSS, and Storybook can improve your workflow and consistency and reduce errors. Tune in for engaging debates and actionable tips on optimizing your design and development process. Whether you're a seasoned developer or just starting, this episode offers valuable takeaways you won't want to miss.

00:00 Introduction

01:50 Defining Design Systems and Their Importance

03:22 The Role of Figma in Design Systems

07:51 Tailwind CSS and Its Impact on Design Systems

10:28 Exploring Storybook and Its Alternatives

17:32 Design Systems in Mobile Development

22:04 Collaboration Between Designers and Developers

33:02 The QA Process and Design Review

34:48 Balancing Design Review with Development Cycles

37:52 Upcoming Conference Talk on Design Systems

YouTube Content on Design Systems:

Tools and Libraries:

Elixir Live Storybook: Elixir Live Storybook
MediCode Application: MediCode AI/ML Product
View Component (GitHub): View Component
Lookbook (Storybook for View Components): Lookbook

Chromatic:

Chromatic: Chromatic Visual Testing Tool

Tailwind:

Tailwind CSS: Tailwind CSS

Figma and Design Systems:

Figma: Figma Design Tool
Headway Design Systems Course: Headway Design Systems Course
Shipwright Design System by Headway: Shipwright Design System

Even-Keeled is a podcast by Headway, a digital product agency.

https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

05: AI and Machine Learning for Software Development in 2024

jon@headway.io (Tim Gremore, Dan Diemer, Chris Held, Jon Kinney) — Tue, 12 Mar 2024 18:27:57 +0000

Exploring AI in Development: Tools, Privacy, and Local Hosting Insights

The Headway development team dives into various aspects of artificial intelligence (AI) and machine learning (ML) in development. Discussion topics range from using AI tools such as ChatGPT in browsers and code editors (including VS Code and Vim), to addressing privacy and security concerns surrounding AI. They explore options for running large language models (LLMs) locally to mitigate privacy issues and highlight Headway's internal developments in the AI space. The conversation also touches on consumer-facing AI tools, troubleshooting development issues with AI assistance, and the potential of hosting AI models locally for development purposes, showcasing Elixir's potency in the ML ecosystem through projects like Medicode and tools such as Live Book.

01:13 Exploring AI Tools and ChatGPT Experiences

08:27 AI in Code Editors: Enhancing Developer Productivity

23:13 The Future of AI in Troubleshooting and Development

33:10 Local Hosting of LLMs and Elixir's Role in AI

41:41 Wrapping Up: AI Innovations and Future Directions

Even-Keeled is a podcast by Headway, a digital product agency.

https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

2024 Reboot: What's Going on Lately with the Headway Development Team

jon@headway.io (Jon Kinney, Dan Diemer, Chris Held, Tim Gremore) — Thu, 22 Feb 2024 12:00:00 +0000

We're back! Join the Headway development leadership team for a chat about RailsConf, Vim and VS Code, PWAs, Turbo Native, Rails 8, Elixir, React, and more.

We discuss recent steps Apple has taken constraining the capabilities of Progressive Web Applications (PWAs) in the European Union. The team also explores TurboNative, a tech solution that blends native and web apps, and Supabase, an open-source Firebase competitor built on Postgres. The resurgence in popularity of the Ruby on Rails framework is also discussed. The episode suggests that while JavaScript libraries like React continue to dominate, full-stack solutions offered by platforms like Rails are experiencing a revival, particularly for start-ups.

00:00 Introductions and Discussion on Technology Trends and Workflows

00:54 Exploring the World of Programming with Core Technologies

01:21 RailsConf and the Journey of Submitting a Talk

02:33 The Vim vs VS Code Debate

08:23 Exploring Other Editors and the Power of Vim

13:26 Apple's Decisions on PWAs and its Impact

19:15 Introduction to Turbo Native

19:51 Turbo Native vs Other Systems

20:54 Turbo Native's Unique Features

22:09 Turbo Native for iOS and Android

22:34 Benefits of Turbo Native for Clients

24:55 The Evolution of React and Rails

25:51 The Resurgence of Rails

26:51 The Future of React and Rails

27:33 The Flexibility of React

36:14 The Use of Supabase in Projects

38:56 The Challenges and Rewards of Consulting

39:51 Preview of Next Discussion: AI, ML, and Cloud Native

Hear from Jon Kinney, Partner & CTO, Tim Gremore, Development Lead, Dan Diemer, Mobile Lead, and Chris Held, Development Lead.

Even-Keeled is a podcast by Headway, a digital product agency.

https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

03: Static Sites with Gatsby (ft. Jacob Hebert & Matt McGee of Headway)

jon@headway.io (Jacob Hebert, Jon Kinney, Matt McGee) — Mon, 4 Jan 2021 17:09:14 +0000

In this episode, Jon chats with Jacob Hebert and Matt Mcgee from the Headway development team about creating static sites with Gatsby. They dive into their experience with Gatsby on client projects and solutions they’ve found most helpful for CMS integration, styling, SEO, and more.

Even-Keeled is a podcast by Headway, a digital product agency.

https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

02: Team Retrospectives (ft. Andrew Stuntz of Headway)

jon@headway.io (Andrew Stuntz, Jon Kinney) — Mon, 3 Aug 2020 18:37:24 +0000

Team retrospectives are a great way to understand what your team can improve on after completing a project. In this episode, Jon chats with Andrew Stuntz, Senior Developer at Headway, about specific ways you can make your team's retrospectives more impactful. That way you can get the most out of your meetings, prevent your team from talking in circles, and do better work together.

Even-Keeled is a podcast by Headway, a digital product agency.
https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

01: The Art of Storytelling in Product Development

jon@headway.io (Jon Kinney) — Sat, 1 Feb 2020 03:38:57 +0000

In this episode, we discuss storytelling through pull requests and git commit messages and dig into how to effectively use git rebase to craft the story of your code.

Even-Keeled is a podcast by Headway, a digital product agency.
https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)

The Craft of Creating Apps and Effective Software Development Teams

jon@headway.io (Jon Kinney) — Fri, 31 Jan 2020 14:56:42 +0000

Jon Kinney, Partner & CTO, and the development team at Headway explore development methodologies and best practices that help teams build successful software. Learn about the format and content of the podcast as well as some background about your host.

Even-Keeled is a podcast by Headway, a digital product agency.
https://www.headway.io/

### ABOUT EVEN-KEELED

### ABOUT HEADWAY

Headway is a digital product agency building web and mobile apps for companies from startups to enterprise. Venture builders, not vendors.

🌐 Headway Website: [https://www.headway.io](https://www.headway.io)

📞 Book a Free Consultation: [https://www.headway.io/free-consultation](https://www.headway.io/free-consultation)