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Engineering · AI · Leadership

Diary of a CTO

Reporting from inside the systems, decisions, and people shaping technology.

Venn diagram of Anthropic and OpenAI overlapping on independent AI safety evaluators

AI Governance · Diary of a CTO

Anthropic and OpenAI Say They'll Embed Independent AI Safety Evaluators — Can They Actually Stay Independent?

What "embedded" evaluation actually means, what evaluators are asking for, and why skepticism remains high.

The journal

All analysis.

Long-form thinking for people building and leading technology organizations.

01AI GovernanceAnthropic and OpenAI Say They'll Embed Independent AI Safety Evaluators — Can They Actually Stay Independent?Diary of a CTO02AIWhen Software Starts Exercising Engineering JudgmentLinkedIn03AgentsMy agents don't know the other agents exist. That's the part that should scare you.Substack04SecurityClaude Breached Three Real Companies. Days Later, It Wiped a Database Too.Substack05SecurityOpenAI Just Proved Why AI Agents Need a Kill SwitchSubstack06CostWhy AI Agent Token Costs Are So Hard to ControlLinkedIn07CostYour token bill is not an AI problem. It is the same infrastructure trap from 2019.LinkedIn08AgentsThe web was built to exploit you. Agents don't care.LinkedIn09AgentsI studied how humans make decisions. Agents have none of those weaknesses.Substack10SecurityThe Composio Breach Exposed the Hole SOC 2 Was Never Built to SeeLinkedIn11SecurityYour SOC 2 certification says nothing about your agentsSubstack12LeadershipThe CTO who'd rather hire a junior than build the AI.Substack13ToolingClaude Code forgets everything when you close it. Someone built a fix and open sourced it.Substack14LeadershipWhat if I never felt like an imposterSubstack15LeadershipFail fast is terrible advice. Here's what actually works.LinkedIn16CultureThe three things that actually drive engineering culture (and it's not ping pong tables)LinkedIn17CultureThe Best Engineering Teams Do Not Document. They Build Systems That Remember.LinkedIn18DevOpsDevOps Was Built for Humans. Agentic DevOps Won't Look the Same.LinkedIn19DevOpsDevelopers Are Getting Replaced. DevOps Is Not Ready for That.LinkedIn20DevOpsYour DevOps Stack Was Built for Google, Not for YouLinkedIn21CareerI talked to a CTO who built a profitable startup, shut it down, and went back to being an ICLinkedIn

From the CTO chair

The podcast archive.

Unfiltered conversations with the leaders responsible for how software actually gets built.

021

How CEOs and CTOs Can Align on Reporting & Decision-Making

Latest

Shailesh Hegde · CEO, Hubilo

TopicStrategy & Business
020

Cost Capitalisation and Platform Engineering

Alper · Head of Platform Engineering, Choco, Berlin

TopicPlatform & Scale
019

DORA Metrics Secrets Every Engineering Leader Should Know

Nathen Harvey · DORA Research Lead, Google Cloud

TopicAI & Engineering
018

Gaming Engineering: Speed, Quality, and Scale Explained

Pranabjyoti Bordoloi · AVP Engineering, Junglee Games

TopicPlatform & Scale
017

How a QA Became an Engineering Leader

Daniel · Head of Engineering Delivery, Valocity

TopicLeadership Transitions
016

How Engineering Leaders Manage Between Urgent and Important

Toshita Pandey · Engineering Leader, Startups & MNCs

TopicTeam Culture & Performance
015

How to Create High-Performing & Self-Organising Engineering Teams

Shalabh Aggarwal · CTO, CredFlow

TopicTeam Culture & Performance
014

Align, Build, Capitalise — Cost Capitalisation and Engineering Management

Dhanush Hetti · Engineering Leader, US & SE Asian Startups (20+ yrs)

TopicStrategy & Business
013

Boost Team Productivity Without Increasing Headcount

Shira Haddad · Engineering Leader, Health Tech & Maritime

TopicTeam Culture & Performance
012

Engineering Long-Term Productivity

Nathan Dench · Engineering Leader, ProcurePro

TopicStrategy & Business
011

Building Trust in Engineering Teams

Sundi Myint · Software Engineering Manager, Cars Commerce

TopicTeam Culture & Performance
010

Team Health and Tech Leadership

Brad Taylor · Former CTO, Nursa | Tech Consultant (Health & Climate)

TopicTeam Culture & Performance
009

AI and Career Growth — An Insider's View

Hunter Powers · Tech Veteran, Engineering Leadership

TopicAI & Engineering
008

Ag-Tech Engineering — Game Dev, Leadership & AI

Anton Zaides · Director of Engineering, Taranis

TopicAI & Engineering
007

Building 10x Engineering Teams

Mitch Pirtle · CTO & Co-founder, RevDoc | Joomla

TopicTeam Culture & Performance
006

How Can Engineering Get a Seat at the Business Table?

Sebastiano Armeli · Director of Engineering, Upwork (ex-Snapchat, PayPal, Pinterest)

TopicStrategy & Business
005

Engineering Management & Culture Beyond the ZIRP Era

Shreyas Balakrishna · Engineering Manager, Culture Amp, Melbourne

TopicStrategy & Business
004

From Mining Engineer to CTO — Scaling Teams 10x and Betting on AI Early

Varun Pandey · CTO, FieldAssist (ex-Mining Engineer)

TopicLeadership Transitions
003

What AI Actually Changes About Engineering Leadership

Manas P. · Head of Engineering, Loopr AI

TopicAI & Engineering
002

From Silicon Valley to India — What the Move Teaches About AI and Engineering Leadership

Sarvesh · VP of AI, Accurate

TopicAI & Engineering
001

Why Fintech Engineering Fails Without Domain Expertise

Varun Bhanot · Engineering Leader, Tata Digital (ex-BlackRock, Fidelity, Grip)

TopicStrategy & Business
Himanshu Saxena, founder and host of Diary of a CTO

Founder and editor

Himanshu Saxena.

Two decades at the intersection of platform engineering, AI, and organizational scale—now documenting the reality of technical leadership.