PRINCIPAL ENTERPRISE ARCHITECT & SYSTEMS STRATEGIST

Ross Rondeau

For 20+ years, I've helped organizations bridge the gap between "it works" and "it scales," leading technology teams through the operational challenges of rapid growth. I build systems that perform under pressure, meet audit and compliance requirements, and allow engineers to focus on innovation instead of firefighting. My work spans cloud, AI, and FinOps strategy at enterprise scale, as a software delivery manager and director.

Everything below is the working catalog: the newsletter essays, the projects and calculators they came out of, and the trip plans built on the same systems thinking. Filter it by series, search it, or subscribe to any slice of it by RSS.

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The Cost of Not Looking Newsletter

Executive essays on the invisible liabilities, hidden costs, and operational blind spots in enterprise technology. Each piece takes one failure that organizations pay for quietly, cloud spend nobody owns, delivery processes that scale badly, decisions deferred until they become expensive, and works through what it actually costs and what to do about it. Written for the people who have to fund and defend those decisions. Articles are grouped into series below, and each series has its own feed.

Tech Series

Leadership Series

Time Optimization Series

Career Development Series

Strategic Perspectives

Projects

Active projects, frameworks, and platforms.

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Trip Planner Content Hub

Multi-horizon vacation blueprints, curated travel writeups, and logistics itineraries with automated route validation, dog-friendly filters, and offline-first static web distribution.

7-Day 7-Week 7-Month
📍 Next Horizon: Door County Autumn Harvest & Wine Trail Weekend (Sep 18 - 20, 2026)
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AI Build vs Buy Break-Even Calculator

Calculate the exact financial break-even point where in-house AI engineering beats commercial LLM API SaaS subscription costs over multi-year horizons.

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Car Buy vs Lease Planner

Compare paying cash, financing, and leasing across the hold length you actually intend, in present value terms, net of what the car is worth when you are done with it.

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Retirement Coast & Milestone Calculator

Calculate your Coast FIRE milestone where compound investment growth fully funds your target retirement portfolio without requiring additional annual savings.

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Wasted Time & Inefficiency Cost Calculator

Quantify the true annual financial cost of recurring workplace interruptions, unproductive meetings, and long commutes based on your loaded hourly compensation.