CIOPages
For CIOs, CTOs and enterprise architects

The six jobs that decide your enterprise’s technology future, and how to get each one done.

For each job: the decisions to make, what practitioners learned, and the guides, blueprints and apps to finish the work.

The six jobs

Pick the job in front of you.

Each job page sets out the decisions, what practitioners learned doing the job, and the guides, blueprints and apps that get it done.

Job 01

Decide where AI goes in the business

The board wants an AI plan, and every function wants to go first.

You leave with
  • A ranked list of the work AI should take on first
  • For each use, how much the AI does alone and where a person signs off
  • The platforms and vendors worth a shortlist
Open the job →
Job 02

Govern the AI already in use

Staff already use AI tools nobody approved, and most SaaS products now ship AI features by default.

You leave with
  • An inventory of the AI already running
  • An acceptable use policy and risk tiers
  • A review that new AI passes before it goes live
Open the job →
Job 03

Choose and buy technology

Every vendor now sells AI features, and each contract runs for years.

You leave with
  • A shortlist built from vendors compared side by side
  • The questions to ask before you sign
  • Each vendor's own answer on who it is not right for
Open the job →
Job 04

Control technology spend

AI is billed per use, so its cost grows with adoption while the rest of the budget is under review.

You leave with
  • Cost models that compare options over several years
  • The steps others took to cut cloud and SaaS spend
  • Market figures that put your budget in context
Open the job →
Job 05

Modernize the estate

AI agents need clean data and systems they can call, and old systems block both.

You leave with
  • A map of the business to plan changes against
  • The steps and pitfalls of each migration or exit
  • Which systems to retire, replace or keep
Open the job →
Job 06

Secure and comply

AI agents act on systems with their own identities, and auditors and boards ask about them.

You leave with
  • The work plan for SOC 2, CMMC, ISO 27001 or NIS2
  • A board report on cyber risk
  • The security products worth a shortlist
Open the job →
Decision apps

Have the analysis done before the meeting.

Enter your situation and each app returns a working document: an AI readiness score, the net return on AI tools after review and rework, a multi-year cost comparison with break-even, a drafted security questionnaire.

See all the apps →No charge. Sign in with your work email.
TCO / ROI BuilderExample result
A custom data platform for 250 users. Build: 4 engineers for 6 months. Buy: $600 per user a year, plus $55k to implement. 5 years, 10% discount rate.
Build total cost
$774k
Buy total cost
$925k
Savings by building (NPV)
$86k
Breakeven
Month 37
Run it with your own figures →
AI Capability Gap AnalyzerAssess your organization's AI readiness across data, talent, governance, and infrastructure.AI ROI Reality CheckCut through tokenmaxxing — translate AI-tool spend and claimed productivity into net realized value after review, rework, and the maintenance tax on generated code.Vendor Security Questionnaire Auto-FillerDraft answers to vendor security questionnaires from your security profile, with placeholders for details to fill in.Technology Landscape AdvisorVendor-neutral analysis of any technology challenge, calibrated to your industry and stack.Shadow AI Exposure RegisterInventory the AI-built apps and automations sprawling across your org, score each on data, blast radius, and ownership, and assign a disposition before they become incidents.Cloud Commitments OptimizerCompare staying, switching or renegotiating a cloud commitment, from your own contract terms.
Inside CIOPages
Buyer Guides
174
vendor comparisons
180
AI transformation blueprints
19
free calculators and tools
73
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1,700+
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