/engineering-leadership
Posts touching engineering leadership.
42 posts
- April 12, 2026 4 min
The portfolio is the proof. Ship your work or it did not happen.
Not resumes. Not endorsements. Not interview performance. The code you ship, the systems you build, the writing you publish. Ship it or it did not happen.
- /career
- /engineering-leadership
- /architecture
- /experience
- April 5, 2026 4 min
What I got wrong in my first year as Head of Engineering and what I would do differently
Over-hiring before culture. Saying yes to everything. Underinvesting in developer experience. Staying hands-on too long. The common thread was not trusting the team.
- /engineering-leadership
- /career
- /decision-making
- /team-building
- /experience
- March 15, 2026 5 min
The real job of a Head of Engineering
Make throughput predictable and quality sustainable. Not hero-shipping. Not writing the most code. Build a system that delivers without depending on any single person.
- /engineering-leadership
- /career
- /decision-making
- /cross-functional
- /blog
- March 10, 2026 5 min
Architecture debt is usually a decision-quality problem first
The worst architecture debt comes from low-quality decisions made with plenty of time. Improving decision quality reduces debt faster than refactoring sprints.
- /architecture
- /engineering-leadership
- /decision-making
- /blog
- March 5, 2026 5 min
Engineering teams do not need more process. They need better defaults.
Every incident triggers a new process proposal. The real fix is better CI pipelines, better templates, and better linters. Better defaults scale. More process does not.
- /engineering-leadership
- /team-building
- /ci-cd
- /decision-making
- /blog
- March 1, 2026 5 min
How I evaluate build-versus-buy decisions at a 50-person startup
Build-versus-buy is not about cost. It is about where your team's attention goes. Build what differentiates. Buy the commodity.
- /engineering-leadership
- /architecture
- /decision-making
- /startup-life
- /blog
- February 28, 2026 4 min
What AI changes about engineering leadership
Code review matters more than code writing. Architectural taste matters more than implementation speed. Evaluating AI-generated code is the new critical skill.
- /ai-ml
- /engineering-leadership
- /hiring
- /decision-making
- /blog
- February 20, 2026 4 min
Startup speed and enterprise readiness are not opposites
Audit logging, RBAC, and proper error handling actually accelerate delivery by eliminating rework. Enterprise readiness is a speed multiplier, not a speed tax.
- /engineering-leadership
- /startup-life
- /architecture
- /financeops
- /blog
- February 9, 2026 4 min
Opus 4.6 has a million-token context window and I am still not sure what to do with it
Feeding entire codebases into a single prompt for architecture review produced mixed results. The practical sweet spots are narrower than the capability suggests.
- /ai-ml
- /engineering-leadership
- /decision-making
- /learning
- January 19, 2026 4 min
Cross-functional alignment is not a meeting problem. It is an incentive problem.
Restructuring OKRs so engineering, product, and sales shared a single top-line metric per quarter fixed what years of alignment meetings could not.
- /engineering-leadership
- /cross-functional
- /startup-life
- /blog
- January 5, 2026 5 min
The hardest conversation I had in 2025 was firing a senior engineer I had hired
He interviewed brilliantly but could not operate in a startup. Performance management is the most important and least taught leadership skill.
- /engineering-leadership
- /team-building
- /hiring
- /decision-making
- /experience
- December 15, 2025 4 min
How I budget engineering time and why I give 20 percent to platform work non-negotiably
Twenty percent of every sprint goes to platform work. The compounding cost of deferring platform investment is measurable in incident frequency and developer velocity.
- /engineering-leadership
- /decision-making
- /startup-life
- /blog
- December 1, 2025 5 min
Opus 4.5 is the first AI model I trust to refactor production code unsupervised
Claude Opus 4.5 refactored a 500-line TypeScript module, maintained all tests, and passed review without modification. The bottleneck has shifted from writing to reviewing.
- /ai-ml
- /engineering-leadership
- /typescript
- /blog
- November 24, 2025 4 min
When your SLOs and your sales team disagree, the SLOs lose
An enterprise prospect required 99.99% uptime. Our SLOs were 99.9%. Engineering leaders who refuse to engage with commercial reality get bypassed.
- /engineering-leadership
- /cross-functional
- /financeops
- /observability
- /blog
- November 17, 2025 4 min
Fifteen years of writing code and I still mass-delete my first draft
The first draft reveals the problem's shape. The second draft solves it. Engineers who try to write perfect code on the first pass are optimizing for the wrong thing.
- /career
- /engineering-leadership
- /architecture
- /experience
- November 3, 2025 4 min
Why your engineering strategy document is probably a wish list, not a strategy
A strategy is a diagnosis, a guiding policy, and coherent actions. Everything else is a roadmap pretending to be a strategy.
- /engineering-leadership
- /architecture
- /decision-making
- /blog
- October 20, 2025 4 min
I mass-deleted our internal wiki and started over. Twice.
The wiki grew to 400 pages that nobody read. The fix was not better organization. It was aggressive pruning and a decay policy.
- /engineering-leadership
- /team-building
- /decision-making
- /experience
- October 13, 2025 4 min
Managing up to a non-technical founder without losing your integrity
Business-outcome framing for every technical decision. Risk quantified in dollars, not story points. Never say "technical debt" without a customer impact number.
- /engineering-leadership
- /startup-life
- /cross-functional
- /decision-making
- /blog
- September 17, 2025 4 min
The one-on-one framework I use after fifteen years of getting one-on-ones wrong
Three fixed sections: blockers with deadlines, career trajectory, and one question the report chooses. Structure creates safety without drift.
- /engineering-leadership
- /team-building
- /career
- /experience
- September 10, 2025 4 min
Sonnet 4.5 replaced our first-pass code review and nobody complained
AI handles style violations and missing error handling. Human reviewers focus on architecture and business logic. Review turnaround dropped from 24 hours to 4.
- /ai-ml
- /engineering-leadership
- /ci-cd
- /blog
- August 25, 2025 4 min
How I use Grafana dashboards to run engineering meetings instead of slide decks
Replacing weekly status slides with live Grafana dashboards eliminated performative reporting and forced teams to instrument what matters.
- /observability
- /engineering-leadership
- /cross-functional
- /blog
- August 18, 2025 4 min
The founder said ship in two weeks. I said no. Here is what happened.
A major customer deal hinged on a feature in two weeks. I pushed for three. The extra week saved us on day four.
- /engineering-leadership
- /startup-life
- /decision-making
- /cross-functional
- /experience
- August 11, 2025 4 min
GPT-5 shipped and my team asked if we still need junior engineers
The answer is yes, but for reasons that forced us to articulate what junior engineers actually contribute beyond lines of code.
- /engineering-leadership
- /ai-ml
- /hiring
- /decision-making
- /blog
- August 4, 2025 4 min
Why I stopped asking candidates to whiteboard and started asking them to review pull requests
Whiteboard coding measures performance under artificial stress. PR reviews measure what the job actually requires.
- /hiring
- /engineering-leadership
- /team-building
- /blog
- July 14, 2025 4 min
The Kubernetes upgrade that taught me release engineering is a leadership problem
A Kubernetes 1.34 upgrade stalled for six weeks not because of technical complexity, but because nobody owned the migration sequence.
- /kubernetes
- /engineering-leadership
- /ci-cd
- /learning
- July 7, 2025 4 min
Two years in and I finally stopped rewriting the org chart every quarter
Constant restructuring is a symptom of unclear ownership, not wrong structure. Org charts stabilize when decision rights are explicit.
- /engineering-leadership
- /team-building
- /startup-life
- /experience
- June 30, 2025 5 min
Eighteen months in: the five things I would tell myself on day one as Head of Engineering at a startup
Delegate before you are ready. Learn compliance before it learns you. Your cofounder's priorities are not wrong, just different. Tech debt compounds faster than you think. And the hardest one: your job is not to write the best code.
- /engineering-leadership
- /startup-life
- /decision-making
- /career
- /experience
- June 19, 2025 5 min
The on-call rotation that was just me, and why I finally admitted that was not sustainable
For 14 months I was the only person who got paged at 3 AM. The real reason was not team size. It was that I did not trust anyone else to handle production incidents.
- /engineering-leadership
- /team-building
- /observability
- /startup-life
- /experience
- June 9, 2025 4 min
Cross-functional friction is a feature, not a bug, if you build the right feedback loops
For months I treated pushback from product, sales, and compliance as obstacles to velocity. The reframe: friction between teams is signal about misaligned priorities, and the right response is better feedback loops.
- /cross-functional
- /engineering-leadership
- /financeops
- /team-building
- /experience
- May 26, 2025 5 min
Claude Opus 4 and Sonnet 4: the week AI coding tools stopped being novelties and became infrastructure
When Claude Opus 4 hit 72.5% on SWE-bench and solved a TypeScript generics issue that had stumped our team, the conversation shifted from "should we use AI" to "how do we integrate it."
- /ai-ml
- /typescript
- /architecture
- /engineering-leadership
- /blog
- May 12, 2025 5 min
Founder dynamics: when your technical opinion conflicts with the CEO's investor promise
The CEO told investors we would launch a new vertical by Q3. I told the CEO we needed Q3 for infrastructure debt. We were both right, which made it worse.
- /engineering-leadership
- /startup-life
- /cross-functional
- /decision-making
- /experience
- April 21, 2025 4 min
OpenAI o3 and o4-mini: reasoning models are getting good enough to replace junior code review
o3 drops 20% fewer major errors than o1, and o4-mini makes reasoning affordable for CI pipelines. A financial calculation rounding error caught by AI review that three humans missed.
- /ai-ml
- /ci-cd
- /typescript
- /engineering-leadership
- /blog
- April 14, 2025 5 min
Why I stopped mass-applying "best practices" and started asking "best for what"
Microservices, event sourcing, CQRS, DDD. I had been cargo-culting patterns from companies 100x our size. The question "who benefits from this complexity" changed my architectural decisions.
- /architecture
- /decision-making
- /engineering-leadership
- /startup-life
- /experience
- March 31, 2025 5 min
The quarterly planning meeting that taught me product managers and engineers solve different problems
I walked into Q2 planning with technical improvements. Product walked in with customer churn data. We talked past each other for two hours before building a framework to bridge both worldviews.
- /cross-functional
- /engineering-leadership
- /financeops
- /startup-life
- /experience
- March 10, 2025 5 min
Learning to delegate when every task feels faster to do yourself
For six months I was the bottleneck on every code review, architecture decision, and production deploy. Delegation felt slower because it was. The turning point was redefining my job.
- /engineering-leadership
- /team-building
- /startup-life
- /decision-making
- /experience
- February 17, 2025 5 min
Claude 3.7 Sonnet's extended thinking and what it means for code review at a small team
Extended thinking mode changed how I approach code review on a team too small for dedicated reviewers. Step-by-step deliberation catches subtle type issues that fast-pass models miss.
- /ai-ml
- /ci-cd
- /engineering-leadership
- /typescript
- /blog
- February 3, 2025 5 min
The tech debt spreadsheet that made my cofounder finally understand why we need a refactoring sprint
Saying "we have tech debt" to a non-technical cofounder is meaningless. A spreadsheet mapping each debt item to customer-facing risk and remediation cost finally moved the conversation.
- /engineering-leadership
- /startup-life
- /cross-functional
- /architecture
- /experience
- January 13, 2025 5 min
I mass-rejected 200 resumes and hired the person who asked the best questions in the interview
Our first structured hiring round attracted 200+ applications. The person we hired had a weaker resume than a dozen others but asked questions that revealed deep systems thinking.
- /hiring
- /engineering-leadership
- /startup-life
- /experience
- November 18, 2024 5 min
Hiring engineer number three when you can barely keep engineer number one from burning out
I posted a job listing for our third engineer while privately wondering if our first hire was about to quit. What I got wrong about workload distribution.
- /hiring
- /engineering-leadership
- /startup-life
- /team-building
- /experience
- August 21, 2024 5 min
Full-stack chaos: when the founder, PM, and head of engineering are all you
In a single Tuesday I triaged a database lock, wrote a product spec, pitched an investor, and reviewed a PR. Wearing every hat is a failure mode.
- /startup-life
- /engineering-leadership
- /cross-functional
- /experience
- July 24, 2024 5 min
Hiring our first engineer: the mass-interview process I built as a non-recruiter
No ATS, no recruiter, no playbook. I built the entire hiring pipeline from scratch and we interviewed 30 candidates to make one perfect hire.
- /hiring
- /startup-life
- /engineering-leadership
- /experience
- June 5, 2024 5 min
Startup engineering culture when you are the only engineer
For the first four months I was the entire engineering department. No code reviews, no architecture discussions. Here are the practices I invented to stay honest.
- /engineering-leadership
- /startup-life
- /decision-making
- /experience