Diary of a CTO — diaryofacto.org
Leadership · AI · Platform engineering · Career
Diary of a CTO is the candid, inside-view podcast for technology leaders navigating the AI era. Episodes cover the decisions that don't make it into conference talks: how to restructure an engineering org around AI agents, what harness engineering means for platform teams, how to talk to a board about autonomous operations, and the career transitions that happen when the job of "writing code" fundamentally changes.
What makes it stand out: the diary format means founders and CTOs share real decisions in real time — not sanitised retrospectives. If you're a CTO trying to figure out where AI fits in your org and your roadmap, this is the feed to subscribe to first.
Best episode to start: Any episode on harness engineering, agentic DevOps, or engineering leadership in the AI era.
The Pragmatic Engineer Podcast
Engineering management · Career · Industry trends
Gergely Orosz runs one of the most widely-read engineering newsletters in the world; the podcast extends it with deep-dive conversations on how engineering works at scale. Topics range from engineering management structures to how the biggest tech companies approach platform decisions. High signal, no fluff.
Software Engineering Daily
Architecture · Infrastructure · AI systems
Daily episodes (as the name suggests) interviewing practitioners building significant software systems. Wide coverage: distributed systems, AI infrastructure, platform engineering, database internals, cloud architecture. Excellent for CTOs who want to stay technically current without losing the big picture.
a16z Podcast
AI · Venture · Technology futures
Andreessen Horowitz's podcast covers the intersection of technology and business at the frontier. For CTOs, the AI-focused episodes are particularly relevant — covering model economics, the agent stack, infrastructure bets, and how AI changes company building. Less operational, more strategic.
CTO Craft Podcast
CTO role · Team building · Engineering leadership
Focused specifically on the CTO role — how to build and manage engineering teams, navigate relationships with product and the board, handle technical debt decisions, and grow as a leader. Useful for CTOs at growth-stage companies who are figuring out how to scale themselves alongside the organisation.
Lenny's Podcast
Product · Growth · Engineering-product collaboration
Primarily product-focused, but essential listening for engineering leaders who work closely with product teams. Lenny Rachitsky interviews operators at the best product companies about how they make decisions, structure teams, and think about growth. Helps CTOs speak the language of the product org.
Latent Space
AI research · LLMs · Agent infrastructure
The technical AI podcast for practitioners. Co-hosts Swyx and Alessio Fanelli interview AI researchers, founders, and engineers at the frontier — covering model architecture, agent frameworks, inference infrastructure, and the state of the art in applied AI. Essential for CTOs who want to understand the technical layer underneath their AI investments.
The Engineering Leadership Podcast
Engineering management · Org design · Team scaling
Focused on the human side of running an engineering organisation. Episodes cover performance management, hiring and firing, eng-product relationships, and how to build engineering cultures that retain great people. Useful when the technical challenges are solved and the organisational ones aren't.
SaaStr Podcast
B2B SaaS · Scaling · Go-to-market
Jason Lemkin's podcast is the canonical resource for B2B SaaS founders and CTOs. Covers everything from ARR milestones and hiring timelines to how engineering and sales interact at different growth stages. Essential if your engineering decisions have direct revenue implications.
The Changelog
Open source · Developer tools · Infrastructure
Long-running podcast from the open source world. Broad coverage of developer tools, infrastructure projects, and the people building them. Useful for CTOs tracking which open source bets are gaining momentum — and which tools your teams are likely to adopt before they appear in formal evaluations.
20VC with Harry Stebbings
Venture · Founders · Company building
High-quality interviews with founders and investors at the frontier of company building. For CTOs, the episodes on AI infrastructure companies — the ones building the tools your engineering teams depend on — are particularly useful for understanding where the market is heading.
Stack Overflow Podcast
Developer community · Industry trends · Career
Accessible, wide-ranging conversations about software development culture, tooling trends, and how the developer profession is evolving. Good for staying connected to how developers themselves are thinking about AI, remote work, and career progression — useful signal for any leader managing engineering teams.
How to use this list
Don't subscribe to all twelve. Pick three that match your current focus: one for the technical layer (Latent Space or Software Engineering Daily), one for leadership (Diary of a CTO or CTO Craft), and one for market perspective (a16z or 20VC). Rotate the third slot as your priorities shift.
Also worth reading: best blogs for tech leaders, AI didn't remove engineering judgment, and what is agentic DevOps.