All-in-one AI plugin for ctos
The all-in-one AI plugin for CTOs
One download gives your AI 17 skills, 209 prompts and 3 apps for strategy, vendors, security and roadmaps, so you walk into every meeting prepared.

- 17skills
- 209prompts
- 3apps
- 12Grok bots
What's inside
Your week is a stack of decisions: a cloud renewal, a security gap, a vendor shortlist, a roadmap the board wants in plain language. Each one needs research, numbers and a clear recommendation. Most of that work starts from a blank page, and the clock never stops.
Seventeen skills for your week
Strategy, investment evaluation, vendor selection, cybersecurity, roadmaps, projects and dashboards. Each one turns a messy question into a structured answer you can take to the board.
Two hundred nine ready prompts
Across ten topics, including technology roadmapping, cost benefit analysis, vendor evaluation, cybersecurity strategy, IT project management, talent, privacy, trends, disaster recovery and architecture.
Three apps you can build
An architecture decision retrieval map, an AI use governance console and a market strategy decision workspace. Each one keeps the reasoning and the evidence behind a choice.
Twelve Grok Bot agents
A team of agents that handle investment evaluation, trend analysis, vendor management, project navigation and executive dashboards, so work continues while you are in meetings.
Works in eight AIs
ChatGPT, Claude, Microsoft 365 Copilot, Gemini, Grok, Grok Bot, Cursor and Kimi. One download, the same skills in whichever tool your company already uses.
Daily news and new ideas
Members get a live feed of AI news for CTOs, one new idea every day with the prompt to run it, and automatic updates when skills change.
A day with your plugin
This plugin puts the whole toolkit inside the AI you already use. Ask a question and the right skill takes over. It structures the analysis, drafts the document and lays out the trade offs. You stay the decision maker, with the groundwork already done.
- Morning
You ask the vendor evaluation skill to compare two cloud proposals. It returns a side by side table with security, price and exit terms before your first call.
- Late morning
A board member asks how AI use is tracked. You open the AI use governance console app and get a source linked record of who approved what.
- Afternoon
Budget review. The investment evaluation skill tests three scenarios and a sensitivity range, then summarizes the numbers for your finance update.
- End of day
You ask the trend analysis skill for this week's shifts in cloud and security, and it drafts a short note for your leadership team.
Install it in your AI
Choose the AI you use. No technical knowledge needed: it's a few clicks and some copy and paste.
ChatGPT
Your own GPT on chatgpt.com, plus a plugin for Codex and ChatGPT workspaces. About 5 minutes.
- Download the ChatGPT version and unzip it (double-click the file).
- Go to chatgpt.com, click GPTs in the left menu, then Create, then the Configure tab.
- Name it CTO Assistant. Open
custom-gpt/instructions.txt, copy everything and paste it into Instructions. - Under Knowledge, upload all the files from the
custom-gpt/knowledgefolder. - Paste the lines from
conversation-starters.txtas conversation starters and click Create. - For the daily news, ideas and skill updates: in ChatGPT go to Settings → Apps & Connectors, add the Complete AI Training connector and sign in with your membership. The README shows each click.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Claude
A Claude plugin for claude.ai, the desktop app, Cowork and Claude Code. About 2 minutes.
- Download the Claude version. Keep it zipped.
- Open Claude (claude.ai or the desktop app), click your name at the bottom left, then Settings → Capabilities.
- Click Upload plugin and choose the zip file. Turn the plugin on.
- Start a new chat and type /start. Your cto assistant introduces itself.
- The first time it uses Complete AI Training, Claude asks you to connect: click Connect and sign in with your membership.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Microsoft 365 Copilot
A Copilot agent: set it up yourself in Agent Builder, or give IT the ready app package. About 5 minutes.
- Download the Microsoft 365 Copilot version and unzip it.
- Open Microsoft 365 Copilot (m365.cloud.microsoft/chat) and click Create agent, then the Configure tab.
- Name it CTO Assistant. Paste everything from
agent-builder/instructions.txtinto Instructions. - Under Knowledge, upload the files from
agent-builder/knowledge. Add the starter prompts and click Create. - Working in a company? The
appPackagefolder is a ready app for your IT team, with the Complete AI Training connection built in. The README has a message you can forward to them.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Gemini
Skills you upload to Gemini, a ready Gem, and a Gemini CLI extension. About 2 minutes.
- Download the Gemini version and unzip it.
- Go to gemini.google.com and open Settings → Skills → Upload.
- Upload the
SKILL.mdfiles from theskillsfolder, starting with the folder whose name ends in-assistant. Gemini now uses them by itself. - Prefer a Gem? Open Gems → New Gem, paste
gem/instructions.txtand upload the files ingem/knowledge. - Using Gemini CLI?
gemini extensions installon the folder also connects Complete AI Training for the daily news, ideas and skill updates.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Grok
A Grok Project with all the instructions and files. About 5 minutes.
- Download the Grok version and unzip it.
- Go to grok.com, open Projects in the left menu and click New project. Name it CTO Assistant.
- Paste everything from
grok-project/instructions.txtinto the project's instructions. - Upload the files from
grok-project/knowledgeto the project. - Start your work chats inside this project. Try one of the lines in
conversation-starters.txt.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Grok Bot
One message that sets up a whole team of Grok Bot agents for your job. About 5 minutes.
- Download the Grok Bot version and unzip it.
- Open Grok Bot and create a new bot. Name it CTO Team Lead.
- Open
SETUP-MESSAGE.md, copy everything and paste it as your first message. - The team lead sets up its own role and walks you through adding each specialist bot, one at a time.
- Add the Complete AI Training connector in Grok Bot so your team lead gets the daily news and ideas for ctos.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Cursor
A Cursor plugin with the skills, rules and connection, or project files. About 3 minutes.
- Download the Cursor version and unzip it.
- In Cursor, open Settings → Plugins and add the unzipped folder.
- No plugins in your Cursor? Copy
skillsto.cursor/skillsandrulesto.cursor/rulesin your project, andmcp.jsonto.cursor/mcp.json. - Open the Agent chat and ask what it can do for you as a cto.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Kimi
A Kimi Code plugin, and instructions with files for Kimi chat. About 3 minutes.
- Download the Kimi version and unzip it.
- Kimi chat (kimi.com or the app): start a new chat, paste
kimi-chat/instructions.txtand attach the files inkimi-chat/files. - Keep using that chat for your work: Kimi now acts as your cto assistant.
- Kimi Code: type
/plugins installwith the folder, then/reload. It connects Complete AI Training too.
Download for members
Members download the plugin for every job, with daily news, ideas and skill updates. Or buy this plugin alone for $49, once.
Everything in the plugin
Your AI picks the right part by itself. You can also ask for one by name.
Skills for ctos 17
- cto investment evaluatorScores a project's ROI, payback, and sensitivity, like comparing a data warehouse upgrade against managed cloud alternatives.
- it strategy development assistantBuilds the full IT strategy, from SWOT and KPIs to governance, like a three-year plan for a 500-person manufacturer.
- technology trend analystResearches AI, cloud, and security trends into a decision-ready report, such as whether to adopt private models now.
- cto it project navigatorPlans projects and tracks risk, budget, and stakeholder updates, like a weekly status pack for a delayed ERP rollout.
- cto tech trend roadmapperMaps vendors and emerging tech into forecasts and roadmaps, like scoring three SIEM vendors against your risk profile.
- technology roadmap strategistPrioritizes your roadmap against business goals, budget, and talent, like sequencing platform work before an AI pilot.
Show all 14 skills
- cybersecurity strategy developerCovers security risk, policy, incident response, and metrics, like building a response plan for a ransomware event.
- agency cto advisorGuides architecture, technical debt, and team scaling, like deciding whether to split a monolith this year.
- technology trends analystDelivers sourced trend and vendor comparisons for IT leadership, like assessing whether to leave a legacy provider.
- vendor evaluation assistantVets vendors end to end, from security and pricing to exit, like reviewing a contract's SLA penalties.
- vendor selection and management assistantRuns RFP drafting, comparison matrices, onboarding, and performance reviews, like scoring five CRM proposals.
- executive dashboard generatorTurns raw CSV or database data into a board-ready dashboard, like monthly cloud spend and uptime trends.
- vendor negotiation assistantPrepares negotiations and renewals with pricing and SLA levers, like pushing a discount at renewal time.
- cybersecurity assessment assistantScopes and interprets security assessments, like planning a penetration test and turning findings into fixes.
Plus a start-here assistant, the prompt library and the app builder, and for members the daily brief.
Ready-made prompts 209
- Technology Roadmapping22 prompts, like Align Technology Roadmap with Business Goals
- Cost-Benefit Analysis22 prompts, like Gather Cost-Benefit Data
- Vendor Evaluation23 prompts, like Industry Research and Analysis Report
- Cybersecurity Strategy Development13 prompts, like Cybersecurity Risk Assessment
- IT Project Management16 prompts, like Agile Methodology Coaching
- Talent Management15 prompts, like Source Qualified Candidates
- Data Privacy Compliance27 prompts, like Automate Data Retention Policy Enforcement
Show all 10 topics
- Technology Trend Analysis25 prompts
- Disaster Recovery Planning22 prompts
- Software Architecture Design24 prompts
Apps you can build with AI 3
- Architecture decision retrieval mapLets your architects look up why a design was chosen and when that reasoning changed, without digging through old tickets. Demo included.
- Source-linked AI use governance consoleKeeps a defensible record of everyday AI use, so reviews take less time and risk stays visible. Demo included.
- Assumption-driven market strategy decision workspaceLinks each strategy assumption to its evidence, so revisions are faster and debates are about facts. Demo included.
Your Grok Bot team 12
- CTO Investment EvaluatorGuides CTOs through cost-benefit analysis for technology decisions, from data gathering to final recommendations.
- IT Strategy Development AssistantDevelops and refines IT strategy from market analysis to implementation roadmaps.
- Technology Trend AnalystTracks tech trends and turns them into actionable IT strategy for global IT leaders.
- CTO IT Project NavigatorOversees IT projects from planning through evaluation, with AI support for every phase.
- CTO Tech Trend RoadmapperScans tech trends, assesses impact and risk, and builds roadmaps for CTOs.
- Technology Roadmap StrategistTurns your tech stack and goals into a prioritized, stakeholder-ready roadmap.
- Cybersecurity Strategy DeveloperDevelops and manages your organization's cybersecurity strategy from risk assessment to incident response.
- Cto AdvisorProvides technical leadership guidance for engineering teams, architecture decisions, and technology strategy.
- Technology Trends AnalystTracks and forecasts technology trends for an EVP of IT.
- Vendor Evaluation AssistantEvaluates vendors end-to-end for CTOs, from research to exit strategy.
- Vendor Selection and Management AssistantManages vendor selection, evaluation, and relationships for IT consultants.
- Executive Dashboard GeneratorTurns raw data into executive-ready reports with insights and recommendations.
Get the plugin
Two ways to get it. Most people choose the membership: it includes every plugin and keeps them up to date.
Recommended
Membership
$9 a month, billed yearly
- The plugin for ctos, and for 500 other jobs
- Daily AI news and a new idea every day, inside your AI
- Skills update by themselves
- 900+ video courses and certificates
- Download up to 2 plugins a day
This plugin only
Standalone plugin
$49 once
- The plugin for ctos, for all eight AIs
- All 17 skills, 209 prompts and 3 apps
- Yours to keep, no subscription
- No daily news, ideas or skill updates
Secure payment by Stripe. Bought it already? Use the link in your email.
Questions
What is a plugin, and how do I install it without technical knowledge?
A plugin is a set of instructions and files your AI reads. You download it once and add it to your AI account, usually by uploading a file or pasting a link. No coding, no servers, no IT ticket.
Which AI does it work with?
ChatGPT, Claude, Microsoft 365 Copilot, Gemini, Grok, Grok Bot, Cursor and Kimi. Use the AI your team already pays for. Your chats stay in that tool, so there is nothing new to learn.
What is the difference between the member download and the $49 standalone plugin?
Members get the full plugin plus daily AI news for your job, a new idea every day with the prompt to run it, and automatic skill updates. The $49 one-time standalone plugin has the skills, prompts and apps, but no daily news, ideas or updates.
Is my data safe?
The plugin is instructions and files, not a service that stores your data. Your conversations stay with your AI provider and follow that provider's privacy settings. Nothing is sent to us.
How many downloads do I get?
Members can download 2 plugins a day. That covers this CTO plugin plus one more for another part of your role, or one for a colleague on your team.
Learn to use AI as a cto
The plugin does the work; the learning path shows you how to get the most out of it, step by step.
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