Guides
CTO Guides
Long-form guides for people running engineering organisations. Each one answers a decision rather than a topic, and each is written to be argued with.
AI Conferences 2027: The Verified Calendar
Microsoft Ignite, AWS re:Invent, NVIDIA GTC, Google Cloud Next, HumanX, Ai4, Dreamforce and more, with checked dates, venues and which ones change an enterprise AI roadmap.
Read the guide →Build vs Buy When Building Just Got Cheap
AI collapsed the cost of producing a feature and left the cost of owning it untouched. Why vibe coding, AI slop and seat-price pressure push the same decision the wrong way.
Read the guide →AWS re:Invent 2026 for CTOs
Keynote schedule with times, how to watch, the agent-heavy themes in the 2026 session catalog, and what a CTO should bring back.
Read the guide →Buying AI: A Procurement Guide for Technology Leaders
Whether to buy at all, what is genuinely different about AI contracts, usage pricing under uncertain load, model-change clauses, and how you leave. With an RFP question set and a due-diligence procedure.
Read the guide →CTO & Engineering Leadership Conferences 2027
Verified dates, cities and prices for the CTO and engineering leadership conferences from November 2026 through 2027, and how to pick the one worth your budget.
Read the guide →CTO Interview Guide: Questions & Prep
Complete CTO interview guide: common questions with sample answers, board presentation prep, salary negotiation, and red flags to watch for. 4-6 round process.
Read the guide →CTO vs VP Engineering: Role, Scope & Career Differences
CTO vs VP Engineering comparison: responsibilities, compensation ($450K-$650K vs $375K-$550K), career paths, org chart placement, and when to hire each.
Read the guide →Engineering OKRs That Work: Examples & Pitfalls
Real engineering OKR examples with measurable key results, plus the anti-patterns that make most engineering OKRs useless. From deployment frequency to developer experience.
Read the guide →Engineering Roadmap Template: Why Roadmaps Fail
Five questions before you commit engineering capacity, outcome vs feature roadmaps, a Now/Next/Later template, and how to cut scope honestly.
Read the guide →Engineering Revenue Attribution: How CTOs Prove Tech Team ROI
How CTOs prove engineering ROI: revenue attribution models, measurement frameworks, and turning tech work into board-level financial impact.
Read the guide →How to Become a CTO: The Career Path
The complete career path from software developer to CTO: stages, timelines, skills at each level, and what the role actually involves in 2026. 12-18 year typical journey.
Read the guide →Beyond OKRs: Engineering Goal-Setting Frameworks
OKRs are over-applied. When they fail and what works better: North Star Metrics, Shape Up, continuous DORA improvement, and bet-based frameworks for engineering teams.
Read the guide →CIO Summits & Pay-to-Meet Programs: Who Pays Whom
How vendors buy time with enterprise tech buyers: Evanta, GDS Summits, Quartz Network, The Millennium Alliance, IQPC, DoGood, The Leadership Board and more, with published terms.
Read the guide →SOC 2 vs ISO 27001: Which One Do You Need?
SOC 2 vs ISO 27001 for CTOs: who asks for which, Type I vs Type II, cost and timeline, doing both, compliance automation tools, and where ISO 42001 fits.
Read the guide →From Cost Center to Profit Center: The CTO's Playbook
Reframe engineering from cost center to profit center: the three moves that change the board conversation, plus the measurement infrastructure.
Read the guide →Technical Debt in the AI Era: A CTO Strategy
AI coding tools create 30-40% more defects on average. How CTOs should manage technical debt from AI-generated code: measurement, prevention, and remediation strategies.
Read the guide →Technical Debt Prioritization: The Framework CTOs Actually Use
How CTOs prioritize technical debt paydown. The RICE-D framework, impact mapping, and practical strategies for balancing debt work against feature development.
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