Sentry’s David Cramer argues prompts are rarely the way to make AI agents behave. I agree: the rules that matter belong in code, as I learnt building Calendrz.
Posts Tagged: CTO
Don’t Forget the Basics!
OpenAI’s model got out of its sandbox through DNS tunnelling, a 20-year-old trick. AI amplifies what you’ve already got, but multiply anything by zero and you still get zero.
Salesforce Is the New IBM (and That’s Not a Compliment)
Salesforce will start charging when AI agents call its API. Straight out of IBM’s mainframe playbook, if you ask me: squeeze the customers who can’t leave.
AI Efficiency or Just Plain Cost Cutting?
Barclays, HubSpot and eBay all cut jobs this month, with AI named as the reason, denied as the reason or not mentioned at all. Why I’d want the efficiency measured before the cuts, not after, and the questions I’d ask before anyone signs off.
Of Leaders, Workers and Too Many AI Agents
A new Asana report finds leaders use far more AI agents than their teams, while workers lose time juggling them. My take on why the two sides see agents so differently, and why leaders should measure finished work rather than agent activity.
Faster Code, Same Release Date: What Gives?
Engineering leaders say AI agents write code much faster, yet their release cycles are no faster than before. Typing was never the bottleneck: here’s where the time really goes, and what I’d change about review and verification.
Of Banks and AI Agents: Lock the Window, Build a Door
JPMorgan and Schwab are blocking outside AI agents from client accounts. They’re right to, but the interesting part is what Schwab offers instead, and why every CTO should give agents a proper front door (as I did for Calendrz).
Build vs Buy in the AI Era
As AI continues to permeate every facet of software engineering, leaders are increasingly confronted with a pivotal decision: Should we build our own AI tools or buy existing solutions? This isn’t just a technical choice; it’s a strategic one that can significantly impact our teams, products, and bottom line. With the upcoming CTO ATX meetup […]
What makes a good CTO?
I have been a CTO myself a few times and worked for some of the greats (and learned!) so I get asked often about what are the traits of a good CTO, be it by the companies I’m advising privately and also through Endeavor mentorship sessions. If you are a co-founder looking for a CTO […]
The Problem with the C-level Exec Who’s Leaving
There has been recently increased attention in the media for Uber, after the blog post from Susan Fowler about her terrible (probably a mild term here, I agree) experience while at Uber — and even more so as of today their SVP of engineering stepping down after sexual harassment allegations during his previous job at […]











