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.
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.
A consistent severity, a blameless postmortem, and a readiness check so the next one hurts less.
A headcount plan, a role breakdown, an org structure, and a ladder to hire against.
Know what data you hold, assess its impact, then answer each framework once and reuse it.
A scored shortlist, a risk assessment, an exit plan, and a defensible build-or-buy call.
A health baseline, a ranked list, a paydown simulation, and the rewrite-or-refactor answer.
A recommended stack, a risk score per technology, a radar to track it, and a diligence verdict.
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
A per-level screening score, the criteria you fail, and the ones it never asked.
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
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
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
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
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
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
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