Explore

Welcome

Crossed over to the dark side. They had promises of impact. They did not mention the budget cycles.

Created: 2020-01-17, last edited: 2026-06-02

About me

Grew up in the codebase: Developer → Tech Lead → Team Lead → Head of Software Development → Director — across C++, Java, C#, and Azure

CTO for the past 5 years, leading an organization of 200+ engineers

Recovering software architect — the instinct never fully goes away

Competent manager, perpetually iterating on the non-technical parts

Fluent in facts, numbers, plans, and processes; less fluent in organizational politics and small talk

50 now with an undiminished obsession for software engineering and the systems that make it work

Why

Countless books, frameworks, and courses cover software delivery, estimation models, and agile methodologies. Yet when I transitioned into engineering management, I immediately felt the gap: no documentation exists for the meta-layer — the coordination overhead, budget cycles, headcount decisions made with incomplete data, and the human systems you suddenly find yourself responsible for.

Boardroom conversations were their own challenge. CFOs optimizing for EBITDA, CEOs thinking in market narratives, investors pattern-matching against portfolio heuristics — they operate on entirely different abstraction levels than engineering teams. Understanding not just what they were asking, but why, took years of trial and error I could have spent building.

These tools and templates are what I wish I'd had from day one. They're purpose-built for the scenarios that actually consume a technical leader's time — so you can spend less of it reinventing infrastructure and more of it on the work that actually scales.

Feedback

I'd be delighted to hear your thoughts on what I'm doing, particularly if you have a differing perspective. Don't hesitate to share, disagreements are always welcome!

Want to print your doc?
This is not the way.

Try clicking the ··· in the right corner or using a keyboard shortcut (

CtrlP

) instead.