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: Ice Age Trail: Bald Bluff Overlook & Stone Elephant (Single-Day Fall Outing) (Oct 18 - 18, 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 True Cost Calculator

Compare buying versus leasing with present-value math, opportunity cost, and actuarial depreciation across 140 vehicles to find your true crossover point.

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Linchpin Cost Calculator

Estimate what it costs to keep a linchpin in place, and what it costs when they leave and pull teammates with them, using your own salary, ramp-up, and turnover assumptions.

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Meeting Cost Calculator

Empirically evaluate any meeting invite: test duration vs deliverables, check mode-to-objective alignment, quantify salary burn, and determine whether to accept, clarify, or decline.

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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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Strategy ToolkitDraft

Build a strategy from vision down to indicator, then check any rung in depth.

4 tools
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Calendar Architecture & Focus Block OptimizerDraft

Map your team's meetings onto a 15-block week, see how many focus blocks they break, and walk through pruning, clustering, and timeboxing to win them back.

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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.