021
How CEOs and CTOs Can Align on Reporting & Decision-Making
LatestShailesh Hegde · CEO, Hubilo
TopicStrategy & Business
A Podcast · Hosted by Himanshu Saxena
THE DIARY
OF A CTO.
Long-form, unfiltered conversations with the engineering leaders shaping how software actually gets built.
Latest Episode
0:000:00
#21
How CEOs and CTOs Can Align on Reporting & Decision-Making
with Shailesh Hegde — CEO, Hubilo
Shailesh pulls back the curtain on one of the most friction-prone relationships in any startup: the CEO and CTO trying to operate in sync. He covers how misaligned reporting structures create confusion at the leadership level, why honesty and clarity beat consensus, and how to broker the customer-vs-innovation tradeoff without breaking team morale.
The Archive
Every Episode.
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
Essays
Writing.
Essays on AI agents, DevOps, security, and engineering leadership — published on LinkedIn and Substack.
01AIWhen Software Starts Exercising Engineering JudgmentLinkedIn02AgentsMy agents don't know the other agents exist. That's the part that should scare you.Substack03SecurityClaude Breached Three Real Companies. Days Later, It Wiped a Database Too.Substack04SecurityOpenAI Just Proved Why AI Agents Need a Kill SwitchSubstack05CostWhy AI Agent Token Costs Are So Hard to ControlLinkedIn06CostYour token bill is not an AI problem. It is the same infrastructure trap from 2019.LinkedIn07AgentsThe web was built to exploit you. Agents don't care.LinkedIn08AgentsI studied how humans make decisions. Agents have none of those weaknesses.Substack09SecurityThe Composio Breach Exposed the Hole SOC 2 Was Never Built to SeeLinkedIn10SecurityYour SOC 2 certification says nothing about your agentsSubstack11LeadershipThe CTO who'd rather hire a junior than build the AI.Substack12ToolingClaude Code forgets everything when you close it. Someone built a fix and open sourced it.Substack13LeadershipWhat if I never felt like an imposterSubstack14LeadershipFail fast is terrible advice. Here's what actually works.LinkedIn15CultureThe three things that actually drive engineering culture (and it's not ping pong tables)LinkedIn16CultureThe Best Engineering Teams Do Not Document. They Build Systems That Remember.LinkedIn17DevOpsDevOps Was Built for Humans. Agentic DevOps Won't Look the Same.LinkedIn18DevOpsDevelopers Are Getting Replaced. DevOps Is Not Ready for That.LinkedIn19DevOpsYour DevOps Stack Was Built for Google, Not for YouLinkedIn20CareerI talked to a CTO who built a profitable startup, shut it down, and went back to being an ICLinkedIn
In the Press
On Air. In Print.
Times Now · On AirWill AI Take Away Your Job? Is an 'AI Takeover' Inevitable?
Panelist on Times Now discussing Ford, IBM and CBA reversing hiring decisions — and what the AI shift really means for engineering jobs.
Zee News · On AirExclusive Newshour Primetime: How Anthropic Is Reshaping the Services Industry
Featured as an AI commentator on one of India's largest news networks.