Something broke. What now?
A consistent severity, a blameless postmortem, and a readiness check so the next one hurts less.
What are you trying to decide?
72 tools for the questions a CTO actually gets asked. Each gives you a result in minutes, and most hand that result to the next one.
No account needed for most of them. See the free list.
Start with the question, not the tool
Each journey is a sequence where one tool's result carries into the next. Pick up where you left off, or start at step one.
How big should the team be, and how should it be shaped?
A headcount plan, a role breakdown, an org structure, and a ladder to hire against.
Are we ready for the audit?
Know what data you hold, assess its impact, then answer each framework once and reuse it.
Which vendor, and how trapped will we be?
A scored shortlist, a risk assessment, an exit plan, and a defensible build-or-buy call.
Which technical debt should we pay down first?
A health baseline, a ranked list, a paydown simulation, and the rewrite-or-refactor answer.
Is our technology stack a risk?
A recommended stack, a risk score per technology, a radar to track it, and a diligence verdict.
Every tool
Compliance & Risk
Comprehensive compliance assessments for GDPR, SOC 2, HIPAA, ISO 27001, and more.
What data do we actually hold, and how sensitive is it?
A classified inventory of your data assets by sensitivity and applicable regulation, exportable to Excel.
Data Classification · 20 min · Generator · Pro
Does this processing need a DPIA, and what are the risks?
A complete privacy impact assessment with risks, mitigations and sign-off, as Markdown or PDF.
PIA/DPIA Generator · 30 min · Generator · Pro
Are we GDPR compliant?New
A readiness score across nine GDPR areas, the gaps, and the actions that close them.
GDPR Compliance · 15 min · Assessment
Are we ready for a SOC 2 audit?New
A score against 51 of the 61 Trust Services Criteria, the gaps by control, and what to fix first.
SOC 2 Readiness · 20 min · Assessment
Do our safeguards meet HIPAA?New
Administrative, physical and technical safeguard scores with the gaps and the penalty context.
HIPAA Compliance · 15 min · Assessment
How far are we from ISO 27001?New
A gap analysis across the Annex A controls with a certification path.
ISO 27001 Gap Analysis · 20 min · Assessment
Where do we sit on the NIST Cybersecurity Framework?New
A tier across the core functions and the categories holding it down.
NIST CSF Assessment · 15 min · Assessment
Can we pass PCI DSS?New
A score across seven domains covering all twelve requirements, plus the validation route for your merchant level.
PCI DSS Checker · 15 min · Assessment
How ready are we for DORA?New
A readiness score across seven ICT resilience domains, with the gaps mapped to DORA articles.
DORA Compliance · 15 min · Assessment
How resilient are our critical services, really?New
A resilience score across Services, Tolerances, Architecture, Monitoring and Proof, aligned to FCA and DORA.
STAMP Operational Resilience · 20 min · Assessment
Is security slowing us down, or not slowing us down enough?New
Your risk tier, a balance verdict, and the decisions that rebalance it.
Security vs Velocity Tradeoff · 10 min · Assessment
How trapped are we by our vendors?New
A lock-in score per vendor, exit triggers, and a migration plan.
Vendor Lock-in Exit Strategy · 15 min · Planner
Is this vendor safe to rely on?
A risk score across security, continuity and stability, weighted by how critical the vendor is.
Vendor Risk Assessment · 15 min · Assessment
Where are our security gaps?
A posture score across every domain with a prioritised checklist.
Security Assessment Checklist · 20 min · Assessment
Is our AI system fair, transparent and accountable?
An ethics maturity score with the gaps in bias, transparency and oversight.
AI Ethics Assessment · 15 min · Assessment
Are we in scope for NIS2, and are we ready?New
Entity classification, a readiness score, and the measures still missing.
NIS2 Readiness · 15 min · Assessment
Do we meet CCPA and CPRA?New
Applicability from your revenue and data volume, a score across consumer rights, and the gaps.
CCPA/CPRA Compliance · 15 min · Assessment
What does the EU AI Act require of our system?
Your system's risk tier and the compliance checklist that follows from it.
EU AI Act Compliance · 15 min · Assessment
Is our product accessible to WCAG 2.2?New
Conformance at your target level with the failing criteria listed.
WCAG 2.2 Compliance · 20 min · Assessment
Can we ship with these open-source licences?
GPL conflicts, commercial compatibility, and the licences to swap.
License Compliance Checker · 10 min · Calculator
Which of our technologies is a risk?
A risk score per technology across eight factors, ready for your tech radar.
Tech Stack Risk Radar · 15 min · Assessment
Architecture & Design
Tools for system architecture, design decisions, and technical planning.
What does our enterprise architecture actually look like?
ArchiMate models across business, application and technology layers, with AI-seeded capabilities.
ArchiMate Modeler · Canvas
Are we building a product, or accidentally a platform?New
A verdict on platform investment with the signals behind it.
Product vs Platform Strategy · 10 min · Assessment
Should we rewrite this system, or is that a trap?New
Rewrite, strangler fig, refactor or leave alone, with a risk-modelled roadmap.
Rewrite vs Refactor · 10 min · Assessment
Should we build this or buy it?
A weighted recommendation with the cost curve and an ADR to file.
Build vs Buy Matrix · 15 min · Calculator
How mature are our architecture practices?
A maturity level per practice area and what the next level takes.
Architecture Maturity Assessment · 15 min · Assessment
Which architecture option should we choose?
Options scored against weighted criteria, ranked with the margin that decides it.
Architecture Decision Matrix · 10 min · Calculator
What breaks if this service goes down?
A ranked blast-radius table with circular dependencies and single points of failure.
Microservices Dependency Mapper · 20 min · Canvas
How risky is this database migration?
A risk score, mitigations, and downtime and rollback estimates for the strategy you pick.
Database Migration Risk Assessor · 15 min · Calculator
How healthy is our codebase?
A health grade across eight areas and where to invest first.
Codebase Health Analyzer · 10 min · Assessment
Which technical debt do we pay down first?
A ranked list by impact, effort and risk, ready to simulate.
Tech Debt Prioritizer · 15 min · Planner
What should this API look like before we build it?
A visual contract, an OpenAPI spec, and a breaking-change report against an earlier contract.
API Contract Designer · 30 min · Canvas · Pro
What does our system actually look like?
An architecture diagram with connections, cost estimates and PNG or SVG export.
System Design Canvas · 30 min · Canvas · Pro
Cloud & Infrastructure
Tools for cloud cost optimization, infrastructure planning, and DevOps.
What will this infrastructure cost on AWS, Azure or GCP?
A monthly estimate per provider with a growth projection.
Cloud Cost Estimator · 10 min · Calculator
Where is our Kubernetes spend being wasted?
Bin-packing waste, per-pod right-sizing moves and spot savings for a single node pool.
Kubernetes Cost Optimizer · 15 min · Calculator
How good is our delivery pipeline?
A CI/CD maturity grade with the capabilities to add next.
CI/CD Maturity Grader · 10 min · Assessment
Would we survive a serious outage?
A continuity maturity score across governance, recovery and drills.
Business Continuity Planner · 15 min · Assessment
Is it the network?
Latency, packet loss and bandwidth measured from the browser, with history.
Connectivity Tester · 5 min · Calculator
What rate limits should this API have?
A token-bucket refill rate and burst capacity sized from your traffic, plus per-tier quotas and burst ceilings.
API Rate Limit Planner · 10 min · Calculator
Team & Organization
Tools for team scaling, organizational design, and people management.
Is my CEO relationship working, or just functioning?New
An alignment score across four dimensions with red flags and a cadence plan.
CTO-CEO Alignment Framework · 10 min · Assessment
Are we slow because of decisions, not technology?New
Decision friction diagnosed, decisions classified, and a delegation model.
Decision Velocity Framework · 15 min · Planner
Is our engineering and product tension productive or destructive?New
A health score, the power balance, and a collaboration model to fix it.
Engineering vs Product Tension · 10 min · Assessment
How should the engineering org be structured?
Team count, spans of control, an org chart and a Conway check.
Engineering Org Designer · 10 min · Planner
How big should the engineering team be?
A recommended size, the role breakdown, and a hiring plan with budget.
Team Scaling Calculator · 10 min · Calculator
How many engineers will we need next year?
A month-by-month headcount forecast with attrition and ramp-up built in.
Headcount Forecasting · 10 min · Calculator
What should we pay for this role?
Compensation bands by role, level and location, exportable to Excel.
Salary Band Calculator · 5 min · Calculator
What should a CTO earn at our stage?New
Base, bonus and equity benchmarks by stage, size and geography.
CTO Compensation Benchmark · 5 min · Calculator
What should we ask in this interview?
Curated questions by role, level and focus, exportable.
Interview Question Bank · 5 min · Generator
Is our on-call rotation fair and sustainable?
A rotation schedule that balances load and protects rest.
On-Call Rotation Optimizer · 10 min · Planner
What does progression look like for our engineers?
A career framework with IC and management tracks and competency matrices.
Engineering Ladder Builder · 30 min · Generator · Pro
How should our teams interact?
A Team Topologies diagram with interaction modes and a Conway check.
Team Topology Designer · 30 min · Canvas · Pro
How do I run 1:1s that actually help?
Structured 1:1s with template talking points, notes and action items that carry over.
1:1 Meeting Assistant · Planner · Pro
Operations & SRE
Tools for incident management, SRE practices, and operational excellence.
What did we learn from this incident?
A blameless postmortem with timeline, five whys and action items.
Incident Postmortem · 20 min · Generator
Are we ready to respond when it breaks?
A response maturity score across preparation, playbooks and post-incident review.
Incident Response Planner · 15 min · Assessment
How severe is this incident?
A consistent SEV level with the reasoning, ready for the postmortem.
Incident Severity Classifier · 3 min · Calculator
What SLA should we commit to?
Tiered targets, penalties and terms as a document you can send.
SLA Generator · 10 min · Generator
Are we shipping features, or shipping learnings?New
An experimentation maturity score and experiments designed with statistical rigour.
Experimentation Framework · 15 min · Calculator
How is the engineering team performing?
DORA metrics and team performance in one dashboard, exportable.
Engineering Metrics Dashboard · 10 min · Planner
Planning & Finance
Tools for budgeting, ROI calculations, and strategic planning.
Is this business idea worth pursuing?New
From idea to lean canvas to a full plan, generated with AI.
Foundry · Generator
Where should we invest, and where should we buy commodity?
A Wardley map of your value chain and how it is evolving.
Wardley Map Builder · 30 min · Canvas
What do I show the board?
An executive deck with KPIs, risks, investments and roadmap, as PowerPoint.
Board Presentation Generator · 30 min · Generator · Pro
Where does AI actually belong in our stack?New
AI maturity, use-case scores, a cost model and governance in one strategy.
AI Adoption Strategy · 20 min · Assessment
How do we plan technology when the business future is unclear?New
Wait, act, hedge or avoid, decision by decision, with optionality built in.
Technical Strategy Under Uncertainty · 15 min · Planner
Is this engineering investment worth it?
NPV, payback and probability-weighted return for an initiative.
Engineering ROI Calculator · 10 min · Calculator
What do we need to ask vendors?
A complete RFP from a 138-question bank with a vendor scorecard.
RFP Generator · 20 min · Generator
What happens if we change the architecture?
Scenarios modelled side by side with the trade-offs quantified.
Architecture Scenario Planner · 30 min · Canvas
How good a CTO am I, honestly?
A self-assessment across the skills that matter, with development areas.
CTO Rating Framework · 15 min · Assessment
How much can the team commit to this sprint?
Available hours against planned points, with meetings and support accounted for.
Sprint Capacity Planner · 5 min · Calculator
Tech Stack & Code Quality
Make informed technology decisions and manage technical debt.
What is hiding in this technology stack?
A proceed-or-not verdict built from five assessments.
Technology Due Diligence · 60 min · Assessment · Pro
What are we adopting, trialling and holding?
A living tech radar with Adopt, Trial, Assess and Hold rings.
Tech Radar Builder · 15 min · Canvas · Pro
Which technologies should we build on?
Scored recommendations from 200+ technologies with an ADR to file.
Tech Stack Decision · 10 min · Generator
What happens if we pay down debt at this rate?
A month-by-month projection of debt, velocity and break-even at your chosen paydown allocation.
Tech Debt Paydown Simulator · 10 min · Calculator