Distributed.

Antony Marcano is the founder of RiverGlide and an engineering leader known for building teams that reach the Elite tier of the DORA metric for software delivery performance. In this episode of Distributed, host Jack Hannah talks with Antony about what distinguishes those teams and how AI is reshaping software delivery.Antony explains why AI-augmented coding often amplifies existing team dynamics, accelerating work upstream of bottlenecks and sometimes harming end-to-end performance. He discusses why humans must still maintain codebases, how overreliance on AI can reduce collaboration, and why leaders should measure delivery performance before adopting tools under top-down pressure.They also explore what return-to-office mandates often miss about remote collaboration, how elite remote-first teams operate, and why DORA remains a useful starting point for understanding performance in the AI era.—Where to find Antony Marcano:• LinkedIn: https://www.linkedin.com/in/antonymarcano • Website: https://antonymarcano.com • Bluesky: https://bsky.app/profile/antonymarcano.bsky.social —Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠• Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠—Timestamps:(00:00) Intro(01:07) The four DORA metrics(03:08) What elite status means(08:50) What excites Antony about AI(12:09) What concerns Antony about AI(15:56) Removing delivery bottlenecks(18:49) AI’s impact on collaboration(22:02) Risks of relying entirely on AI code(27:11) Why collaboration matters in software teams (31:19) Navigating top-down pressure to adopt AI(36:45) Why DORA is a good starting point(39:04) Return-to-office mandates(42:30) Characteristics of elite remote-first teams(47:52) METR study on AI and perceived productivity(50:15) Rapid fire round —Referenced:• RiverGlide: https://riverglide.com• DORA’s software delivery performance metrics: https://dora.dev/guides/dora-metrics• Waterfall Methodology: A Comprehensive Guide: https://www.atlassian.com/agile/project-management/waterfall-methodology• Is Your AI assisted Coding Strategy Quietly Backfiring?: https://www.youtube.com/watch?v=dQ1apxgvOa0• 2025 DORA State of AI-assisted Software Development Report: https://cloud.google.com/resources/content/2025-dora-ai-assisted-software-development-report• OpenClaw: https://openclaw.ai• OpenClaw (formerly Moltbot, Clawdbot) May Signal the Next AI Security Crisis: https://www.paloaltonetworks.com/blog/network-security/why-moltbot-may-signal-ai-crisis• Performance at the Limit: Business Lessons from Formula 1 Motor Racing: https://www.amazon.com/Performance-Limit-Business-Lessons-Formula/dp/0521844002• Measuring the Impact of Early-2025 AI on Experienced Open-Source Developer Productivity: https://arxiv.org/abs/2507.09089• Extreme Programming: A gentle introduction: http://www.extremeprogramming.org• Extreme Programming Explained: Embrace Change: https://www.amazon.com/Extreme-Programming-Explained-5-Oct-1999-Paperback/dp/B011T86NIY• Machine learning expert on the 3 skills that matter most in the AI age: https://tuple.app/distributed/machine-learning-expert-on-the-3-skills-that-matter-most-in-the-AI-age• Jason Gorman on LinkedIn: https://www.linkedin.com/in/jasongorman• The AI-Ready Software Developer – Index: https://codemanship.wordpress.com/2025/10/30/the-ai-ready-software-developer-index• Dave Farley’s blog: https://www.davefarley.net• Kevlin Henney’s website: https://kevlin.tel

In this episode of Distributed, Jack Hannah speaks with Scott Jones, Head of Engineering for Service Delivery at Stash, about building complex systems in a remote-first environment and why real-time collaboration matters more than ever.Scott reflects on helping build Stash’s core banking platform in just one year, breaking down what building a bank actually means from an engineering perspective. He explains how the work was structured across teams, why individual heroics fall apart at scale, and how frequent synchronous coordination helped the team move fast without breaking things.The conversation introduces Scott’s idea of “aggressive huddling,” a practice of using real-time communication with tools like Tuple to simulate in-office collaboration. Through concrete stories, including a critical migration issue resolved before customers noticed, Scott shows how early human coordination can prevent costly failures.The episode also explores how AI is changing engineering work at Stash. As execution becomes faster, Scott argues that collaboration, project management, and problem framing are becoming core engineering skills, and that AI increases the need for human alignment rather than reducing it.—Where to find Scott Jones:• LinkedIn: https://www.linkedin.com/in/scott-jones-bab7b713• Website: https://www.stash.com/ —Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠⁠⁠• Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠⁠⁠—Timestamps:(00:00) Intro(01:32) What it takes to build a bank (05:24) Why the one-year timeline didn’t feel daunting(08:52) Structuring the work across teams (11:14) “Aggressive huddling” on Tuple(14:08) How real-time huddling saved a failing migration(18:47) How real-time coordination works day to day(22:42) Why postmortems can be a collaboration red flag(25:46) How engineers at Stash are using AI today(31:37) The skills that engineers need now (33:50) Why AI tools demand more collaboration(36:07) How time is allocated in an AI-driven workflow(38:33) The future of human-AI collaboration(41:20) Rapid fire round —Referenced:• Stash: https://www.stash.com• Forrest Gump: https://en.wikipedia.org/wiki/Forrest_Gump• Keir Lauritzen on LinkedIn: https://www.linkedin.com/in/keir-lauritzen• Ruby on Rails: https://rubyonrails.org• Test Driven Development: https://martinfowler.com/bliki/TestDrivenDevelopment.html• Uncle Bob Martin on X: https://x.com/unclebobmartin• Justin Martin on LinkedIn: https://www.linkedin.com/in/mythinking• Grok: https://grok.com• Broken Money: Why Our Financial System is Failing Us and How We Can Make it Better: https://www.amazon.com/Broken-Money-Financial-System-Failing/dp/B0CG83QBJ6

Andrew Stellman, a seasoned software engineer and author well-versed in AI and Agile methodologies, shares valuable insights on building high-performing teams. He reflects on his transition to remote work post-9/11 and the necessity of a shared understanding among team members. Discussing AI, he emphasizes that effective use comes from careful engagement and critical thinking rather than blind reliance. Stellman introduces five key habits for developers to harness AI while warning against 'vibe coding'—highlighting the importance of clear communication and understanding in software development.

What does craftsmanship look like in an async-first, remote company?In this episode of Distributed, host Jack Hannah sits down with Steve Schoeffel, co-founder of Whimsical, to talk about async-first work, craftsmanship, and the tradeoffs of running a fully remote company. Steve shares how Whimsical creates momentum without constant meetings, why quality lives in the details, and how async-first work shapes both the product and the company culture.Steve also reflects on the harder, more personal side of the work. He talks candidly about co-founder misalignment, the strain of leadership during periods of uncertainty, and what it’s been like to learn to hold work more loosely over time.They also dig into the return-to-office push and why Steve remains convinced that remote work, done well, is worth fighting for.—Where to find Steve Schoeffel:• LinkedIn: https://www.linkedin.com/in/steveschoeffel—Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠• Website: ⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠—Timestamps:(00:00) Intro(01:02) An overview of Whimsical (02:02) The size of Whimsical’s team and how it operates across time zones(03:08) What the Whimsical Way is and how it shows up in practice (04:58) Why Whimsical is async-first and what that looks like in practice(10:49) How Whimsical maintains energy and connection in async work(13:59) Craftsmanship as a core value at Whimsical(18:21) How Whimsical pursues “insanely great” work(24:14) What’s been hardest about running a remote company(28:24) How Steve realized he and his co-founder were misaligned(32:08) How Steve is learning to detach from work and care for himself(36:32) Why Steve remains pro–remote work amid big tech’s return-to-office push—Referenced:• Whimsical: https://whimsical.com• The State of Async (formerly The Whimsical Way): https://whimsical.com/blog/state-of-async-2026• Kaspars Dancis on LinkedIn: https://www.linkedin.com/in/kasparsd • How async work inspires craftsmanship: https://whimsical.com/blog/how-async-work-inspires-craftsmanship• Development cycles, process, and tooling: https://tuple.app/distributed/head-of-engineering-at-sublime-security-on-development-cycles-process-and-tooling-with-sumeet-jain• Craftsmanship, the heart of Whimsical: https://whimsical.com/blog/craftsmanship-the-heart-of-whimsical• Frank Slootman on LinkedIn: https://www.linkedin.com/in/frankslootman• Shapeup: https://basecamp.com/shapeup

Scott Hanselman, Vice President of Developer Community at Microsoft, dives into the pressing issues in software development today. He discusses how speed-driven incentives often lead to broken software and the diminishing role of craftsmanship. Scott highlights the vital need for better apprenticeship models and mentorship, especially with the rise of AI. He advocates for a preceptor approach to internships, emphasizing long-term investment in developer communities and practical tips to boost team connection and productivity.

Ivett Ördög, a software veteran with 35 years of experience and creator of Lean Developer Experience, discusses how vital communication is for engineers seeking promotion. She emphasizes that remote work can enhance deep focus and well-being, debunks misconceptions about it, and shares tips for improving communication skills. Ivett also tackles effective strategies for pitching rewrites to management, the significance of continuous delivery for fast feedback, and how experiential learning outshines traditional lectures. A treasure trove of insights for engineers!

Jesse Wilson, an experienced engineer from Cash App and a notable contributor to Java and Android, dives into the art of doing things the right way. He discusses the remarkable journey of Okio, the I/O library that has changed the game with over 50 billion downloads, emphasizing the importance of craftsmanship. Jesse also shares insights on fostering collaboration in remote teams through spontaneous interruptions and shared tools. His philosophy highlights that enduring quality in engineering is both rewarding and necessary for long-term success.

As AI reshapes how software is built, what does it actually mean to be a good engineer? Chelsea Troy, who leads Machine Learning Operations at Mozilla and teaches computer science at the University of Chicago, argues that the future of engineering isn’t about typing faster but thinking better.In this episode of Distributed, Chelsea joins host Jack Hannah to unpack the three skillsets that matter most in the age of AI: investigative, evaluative, and innovative thinking. She explains why AI tools still fall short in areas that require human reasoning and judgment, how engineers can uplevel the skills that set them apart, and why collaboration and a solid grounding in computer science remain essential.—Where to find Chelsea Troy:• Website: https://chelseatroy.com• LinkedIn: https://www.linkedin.com/in/chelseatroy—Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠• Website: ⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠—Timestamps:(00:00) Intro(01:08) The 3 most underrated skillsets engineers rely on every day(08:45) How an interpreter workshop and a Rust compiler project revealed AI’s limits(14:59) How to level up investigative, evaluative, and innovative skills(21:25) Why collaboration still matters but isn’t a new challenge created by AI(25:38) The value of early career pair programming and why it’s hard but worth it(29:09) Why pairing with an LLM has value but can’t replace human collaboration(34:33) Formal CS degrees vs. nontraditional paths and why studying CS still matters(43:49) Rapid fire round—Referenced:• What can we expect of LLMs as Software Engineers?: https://chelseatroy.com/2025/07/14/what-can-we-expect-of-llms-as-software-engineers• Bob Nystrom’s blog: https://journal.stuffwithstuff.com/• Tim Peters: https://github.com/tim-one • Crafting Interpreters: https://craftinginterpreters.com• Using the Python Interpreter: https://docs.python.org/3/tutorial/interpreter.html• Alan Turing: https://en.wikipedia.org/wiki/Alan_Turing• Ada Lovelace: https://en.wikipedia.org/wiki/Ada_Lovelace

Charity Majors is a writer, speaker, and the co-founder and CTO of Honeycomb, an observability platform for debugging and optimizing distributed systems.In this episode of Distributed, Jack Hannah talks with Charity about the realities of leading and scaling a distributed company. From why remote work is not best for every situation to the communication tax of distributed management, Charity shares what she has learned about building effective teams, fostering trust, and staying connected in a remote environment. She also reflects on her own leadership journey, from CEO back to CTO, and how greater self-awareness and empathy have shaped her approach to work and life.—Where to find Charity Majors:• Bluesky: https://bsky.app/profile/charity.wtf• LinkedIn: https://www.linkedin.com/in/charity-majors/• Website: https://charity.wtf/—Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠• Website: ⁠⁠⁠https://tuple.app/⁠⁠⁠—Timestamps:(00:00) Intro(01:15) Why remote work isn’t best for everything(03:20) What Charity learned from her viral Bluesky post on RTOs(08:33) Why distributed teams need more and better management(11:33) How to get the most from a remote work experience as an engineer (14:30) Why 10x engineers matter less than 10x teams(18:06) How trust and psychological safety drive high-performing teams(20:58) Signs of a healthy organization for job seekers(24:17) Charity’s transition from CEO to CTO and the challenges of down-leveling(26:31) When stepping back in your career can be the right move(30:44) How self-awareness transformed Charity’s approach to leadership and life(34:42) Rapid-fire round —Referenced:• Honeycomb: https://www.honeycomb.io/• Charity’s post on Bluesky about RTO policies: https://bsky.app/profile/charity.wtf/post/3lq4cgak3vk24• How 37signals handles communication, meetings, and setting work boundaries: https://tuple.app/distributed/How-37signals-handles-communication-meetings-and-setting-work-boundaries-with-Rosa-Gutierrez• In Praise of “Normal” Engineers: https://charity.wtf/2025/06/19/in-praise-of-normal-engineers/• Christine Yen on LinkedIn: https://www.linkedin.com/in/christineyen/• Simon Willison’s blog: https://simonwillison.net/• Dr. Cat Hicks' newsletter, Fight for the Human: https://www.fightforthehuman.com/

37signals embraced remote work long before it became mainstream. Its Shape Up framework helped define how remote product teams ship fast, but not every team inside the company follows the same playbook. In this episode of Distributed, host Jack Hannah sits down with Rosa Gutiérrez, Principal Programmer at 37signals and founding board member of the Ruby on Rails Foundation.Rosa takes us inside SEIP (Security, Infrastructure, and Performance), the team responsible for everything from privacy and legacy app maintenance to large-scale infrastructure moves, such as migrating 37signals off the cloud. She shares how a writing-first culture, asynchronous communication, and a flexible, reactive approach let her team thrive outside of the Shape Up model.—Where to find Rosa Gutiérrez:• Bluesky: https://bsky.app/profile/rosa.codes• LinkedIn: https://www.linkedin.com/in/rosagutierrezescudero/• Website: https://rosa.codes/—Where to find Jack Hannah:  • LinkedIn: ⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠• Website: ⁠⁠https://tuple.app/⁠⁠—Timestamps:(00:00) Intro(01:18) Rosa’s role at 37signals(04:10) How long-form writing is critical to 37signals’ culture(07:34) How Rosa adapted to 37signals’ asynchronous communication and unique work style(10:00) The benefits of asynchronous communication for focus, flexibility, and easy reference(12:08) Why 37signals suits introverts and how they handle in-person meetups(14:25) Why Shape Up doesn’t fit the kind of work Rosa’s team does(17:41) How Rosa’s team prioritizes incoming issues during on-call rotations(21:22) Why Rosa’s flexible work style makes her a perfect fit for SEIP’s reactive team(26:03) The challenge remote workers face in setting boundaries(27:46) A case for getting out of the house to create a better work-life balance—Referenced:• 37signals: https://37signals.com/• Hey: https://www.hey.com/• Basecamp: https://basecamp.com/• Ruby on Rails: https://rubyonrails.org/• Shape Up: https://basecamp.com/shapeup• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp-goods.com/products/shapeup