/cross-functional
Posts touching cross functional.
15 posts
- 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
- 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
- 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
- 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
- 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
- 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 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 28, 2025 5 min
The compliance audit that exposed every shortcut we took in our first year
Our first formal compliance audit surfaced 23 findings. Hardcoded keys, PII in logs, missing audit trails. None malicious, all "we will fix that later." The remediation sprint that followed.
- /fintech
- /security
- /cross-functional
- /architecture
- /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
- February 24, 2025 5 min
When the sales team demos a feature that does not exist yet and engineering finds out from a prospect
A prospect called asking for help configuring a feature our sales deck showed but engineering had never built. The fallout was not the scramble but the trust erosion between teams.
- /cross-functional
- /startup-life
- /financeops
- /decision-making
- /experience
- 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
- December 16, 2024 5 min
The meeting where product, sales, and engineering all had different definitions of "real-time"
Product wanted sub-second dashboard updates. Sales had promised "real-time" reconciliation. Engineering was thinking about eventual consistency with 30-second polling. One word nearly derailed a quarter of work.
- /cross-functional
- /architecture
- /financeops
- /decision-making
- /experience
- November 25, 2024 4 min
Why our compliance team rewrites my API specs and I have learned to be grateful
In fintech, your API surface is a regulatory document. Our compliance officer started redlining my OpenAPI specs and improved our API design more than any tech review.
- /api-design
- /fintech
- /cross-functional
- /security
- /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