Even-Keeled - A Software Development Podcast Podcast By Headway Jon Kinney cover art

Even-Keeled - A Software Development Podcast

Even-Keeled - A Software Development Podcast

By: Headway Jon Kinney
Listen for free

The development leadership at Headway talks through how they're actually building software in the age of AI. From design systems and agentic workflows to vibe-coded apps and more, the team shares what's working, what's not, and what they're learning on real client projects. No hype. Just how the work gets done.Headway Career Success Economics Management Management & Leadership
Episodes
  • Design Systems for AI and Agentic Development
    Apr 17 2026

    How do design systems actually work in an AI-driven development workflow?

    In this episode of Even-Keeled, the Headway team breaks down how they connect design systems directly to agents, why screenshots and vibe coding fall short, and what it takes to keep AI-generated code consistent at scale.

    Jon Kinney (CTO), Tim Gremore, and Dan Diemer explore how tools like MCP servers, agent files, and structured component APIs help agents stay aligned with real design standards, how their team achieved high accuracy by generating agent context from code, and why a design system is more than a UI kit. It is a living framework of rules, documentation, and reusable components that empowers both teams and solo developers to ship faster with fewer inconsistencies.

    Segments:

    00:00 - Introduction

    02:11 - Why design systems are more critical than ever with AI agents

    03:53 - The levels of agentic coding from tab complete to terminal workflows

    04:36 - Why a Figma screenshot only gets your agent so far

    06:37 - When the language of your design system breaks at scale

    07:26 - Connecting your design system to an agent through MCP

    08:40 - Static agents files vs. dynamic MCP connections

    13:11 - Treating AI agents like a new developer on your team

    16:54 - Building an agents file for 90% accuracy out of the gate

    24:00 - What a design system actually is and why it's more than a UI kit

    34:05 - Directing agents at Legos instead of a bin of mixed mashed colors

    Topics Covered
    • Design systems in the age of agentic development
    • Why screenshots and vibe coding break down at scale
    • Using MCP servers to connect agents to real design systems
    • Agent files as lightweight context for consistent UI generation
    • Turning design system code into agent-readable APIs
    • Achieving high accuracy with structured component context
    • Managing drift and keeping AI outputs on the rails
    • Documentation, hooks, and workflows that reinforce consistency

    ### 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)

    Show more Show less
    36 mins
  • How Our Dev Team Actually Ships With AI in Early 2026
    Feb 19 2026

    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 the craft of creating software and effective development teams, hosted by the development leadership at Headway. 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)

    Show more Show less
    50 mins
  • 07: System Architecture and Conway's Law
    May 20 2024
    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 Evolution02:20 Exploring Conway's Law in Software Development04:04 The Challenges of Team Communication and Project Management06:45 Efficiency in Small Teams: The Power of Three09:04 Navigating Full Stack Development and Conway's Law17:14 Innovative Approaches to Hosted Infrastructure Technology27:32 Concluding Thoughts on Conway's Law and the Future of Software Development Resources Mentioned:Conway's Law and The Mythical Man-MonthConway's Law - WikipediaThe Mythical Man-Month by Frederick P. Brooks Jr.Elixir and the Flame PatternElixir LanguageChris McCord’s Flame Pattern Presentation at ElixirConf EUFlame Pattern LibraryFly.io PlatformServerless and Hosted EnvironmentsAWS LambdaSupabaseNetlifyVercelFull-Stack Development and LiveViewLiveView for ElixirHotwire by BasecampReact Server ComponentsRelated Articles and Blog PostsJason Fried’s Tweet on Team Size at 37signalsFly.io Blog on the Flame Pattern in JavaScriptBooks and FrameworksShape Up by BasecampRuby on Rails Framework Even-Keeled is a podcast by Headway, a digital product agency.https://www.headway.io/ ### ABOUT EVEN-KEELEDEven-Keeled is a podcast about the craft of creating software and effective development teams, hosted by the development leadership at Headway. New episodes monthly.### ABOUT HEADWAYHeadway 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)
    Show more Show less
    31 mins
adbl_web_anon_alc_button_suppression_c
No reviews yet