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Hiring Bar & Loop Design

Act as a CTO. Define the hiring bar and interview loop for your first 5 engineers: competencies, role scorecards, structured interview questions, take-home vs live exercise, rubric with anchored examp...

Tags: hiring, CTO, process, onboarding, OKR

Author: tsubasa

Category: leadership | Model: gpt-4o

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Go/No-Go Launch Readiness

Act as a COO-minded CTO. Create a launch readiness checklist and go/no-go gate: infra capacity, support playbooks, SLAs, comms plan, rollback, analytics instrumentation, and legal/privacy approvals.

Tags: launch, readiness, operations, SLAs, analytics

Author: tsubasa

Category: leadership | Model: gpt-4o

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Investor Data Room Checklist

Act as a CTO/CEO preparing a seed round. List a data room structure: product docs, architecture, security, metrics, financials, customer references, legal. Include a 6-slide tech appendix and a KPI gl...

Tags: fundraising, investors, data room, KPIs, story

Author: tsubasa

Category: leadership | Model: gpt-4o

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Pricing & Packaging Matrix

Act as a GTM-savvy CTO. Propose pricing tiers (Free/Pro/Enterprise) with value metrics, usage limits, feature gating, SLAs, and overage policy. Include a migration plan and win-loss hypotheses to test...

Tags: pricing, packaging, GTM, SLAs, experiments

Author: tsubasa

Category: leadership | Model: gpt-4o

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Roadmap Now/Next/Later with Bets

Act as a CTO. Build a roadmap with 3 big bets per horizon (now/next/later), expected impact vs effort, key risks, and kill-criteria. Include a one-slide view for the board and a team backlog mapping.

Tags: roadmap, product, portfolio, risk, board

Author: tsubasa

Category: leadership | Model: gpt-4o

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Security Threat Model (STRIDE)

Threat-model feature <feature> using STRIDE. Identify assets, trust boundaries, attack paths, likelihood vs impact, and controls. Map mitigations to standards (ISO/IEC 27001, SOC 2). Output a table of...

Tags: "CTO;security;STRIDE;risk;controls"

Author: ChatGPT

Category: CTO | Model: GPT-5 Thinking

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Roadmap Prioritization via RICE

Prioritize <backlog> using RICE scoring. Show score breakdown, dependencies, risk heat, and hiring needs. Produce a quarter-by-quarter roadmap, capacity assumptions, and a cutline. Include a one-pager...

Tags: "CTO;roadmap;RICE;planning;capacity"

Author: ChatGPT

Category: CTO | Model: GPT-5 Thinking

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Incident Postmortem Generator

Create a blameless postmortem for incident <id>: timeline, customer impact, 5 Whys, contributing factors, detection gaps, and corrective actions. Propose guardrails, SLO/SLA adjustments, runbooks, and...

Tags: "CTO;SRE;incident;postmortem;SLA"

Author: ChatGPT

Category: CTO | Model: GPT-5 Thinking

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Capacity and Cloud Cost Planner

For workload <service>, model 12-month capacity and cloud cost. Include CPU/GPU, storage, egress, and LLM inference. Compare reserved vs spot vs savings plans. Map to SLOs and traffic seasonality. Out...

Tags: "CTO;FinOps;capacity;SLO;cost"

Author: ChatGPT

Category: CTO | Model: GPT-5 Thinking

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