chief-os

Generate a shareable, generic SaaS KPI dashboard as a brand-new standalone Google Sheet, filled with FICTIONAL sample data (no real company or customer data, no external links). Produces a fully-formed B2B SaaS operating workbook — MRR/ARR, MAU usage, retention (NRR), cash collection, autopay, A/R aging, and per-customer detail across a 42-month history — safe to publish publicly (e.g. on LinkedIn or in a portfolio). Use when someone says "make a generic KPI dashboard", "create a shareable SaaS KPI dashboard", "generate a sample/demo dashboard with fake data", "regenerate the generic dashboard", or "refresh the LinkedIn dashboard".

Get a comprehensive view of how the company is performing across all teams — product, engineering, revenue, customers, and ops. Use when you want to understand what's happening company-wide this week or quarter, where we stand on goals, key wins, and areas to watch. Searches Slack, Notion, and the strategy document. Good for staying informed without being in every meeting.

Assemble board meeting materials, board memos, and board updates. Use this skill when the user mentions board meeting, board deck, board memo, board update, board materials, or is preparing for a board meeting. Also use when compiling cross-functional status updates that span metrics, engineering, sales, support, and hiring. This skill pulls live data from HubSpot (pipeline), GitHub/Jira (engineering), Pylon (support), Notion (initiatives), and Google Calendar (timeline) to build comprehensive board-ready documents.

Plan and manage company events, conferences, and user group meetings. Use this skill when the user mentions event planning, conference, user group, offsite, launch event, hackathon, build day, or asks for a creative brief, agenda, budget, logistics plan, speaker coordination, or post-event content plan. Triggers on "plan an event", "creative brief", "agenda for", "event budget", or when coordinating any company-sponsored gathering.

Prep for a 1-1 meeting. Looks up the other person in the company org roster and checks your calendar to determine if this is a meeting with your manager (→ PPP format: Priorities, Problems, Plans against your goals) or a direct report (→ impact review, talking points, blockers, open items). Pass the person's name or meeting time.

Prep for a 1-1 with a direct report. Pulls the employee's role, goals, and function from the org roster, then searches their function-relevant MCPs (Grain, Slack, Notion, HubSpot for Revenue, Pylon for Support) for the past 5 business days. Returns a prioritized 1-1 agenda with impact highlights, blockers, recognition opportunities, and open items. Use when asked "prep my 1-1 with [name]", "1-1 prep [name]", "what should I discuss with [name]", or "my 1-1 with [name]".

Monitor and maintain competitive intelligence. Use this skill when the user asks about competitors, competitive positioning, battle cards, win/loss analysis, market moves, or how to position against a specific competitor. Triggers on "competitive update", "battle card", "win/loss", "[competitor name] news", "how do we compare to [competitor]", or when preparing sales materials, investor briefs, or strategic memos that require competitive context.

View and update the company context that all Chief of Staff skills depend on. Use this skill when the user says "update context", "update company info", "update metrics", "update org chart", "update voice guide", or any variation of updating the foundational company data. Also use when any other chief-* skill needs to read company context — this is the canonical source.

Analyze deals, term sheets, contracts, and proposals. Use this skill when the user shares a term sheet, contract, proposal, LOI, NDA, MSA, reseller agreement, consulting agreement, venture debt proposal, or any commercial document and wants analysis, comparison, negotiation strategy, or risk assessment. Triggers on "analyze this term sheet", "compare these proposals", "what do you think of this deal", "negotiation strategy", "redline this", or when the user uploads a contract or deal document.

Produce a daily executive digest of external customer and prospect meetings. Use this skill when the user asks for a meeting digest, daily meeting summary, customer meeting recap, prospect meeting notes, or says "what happened in meetings today". Pulls meeting transcripts from Notion (sourced from Fathom or another meeting recorder), synthesizes cross-conversation patterns, and posts the digest to a dedicated Slack channel. Triggers on "meeting digest", "daily digest", "customer meetings today", "what did we learn from calls", or when another chief-* skill needs a summary of recent external meetings.

Synthesize customer escalation data from support tools into actionable intelligence. Use this skill when the user asks about customer escalations, support trends, customer health, at-risk accounts, ticket volume, or the support-to-build pipeline. Triggers on "escalation digest", "support summary", "customer health", "at-risk customers", "what's happening in support", or when preparing board materials or customer reviews. Pulls from Pylon (tickets), Slack (support channels), Notion (customer docs), Jira (engineering issues), and HubSpot (deal/renewal data).

Manage the full fundraising process as a coordinated campaign. Use this skill when the user is actively fundraising or preparing to fundraise. Triggers on "fundraise status", "investor pipeline", "fundraise update", "where are we on the raise", "meeting prep for [investor]", "follow-up for [investor]", "diligence tracker", or when coordinating across multiple investor conversations simultaneously. This skill composes chief-investor, chief-deal, and chief-memo to manage the end-to-end process.

Build the business case and pro forma financial model for a new line of business or strategic initiative. Use this skill when the user wants to evaluate a new LOB, write an initiative proposal, or build a financial model for a new business. Produces a structured memo covering thesis, strategic rationale, operating model, pro forma, legal structure, and risk analysis.

Generate comprehensive investor meeting briefs. Use this skill when the user mentions an investor meeting, says "prep me for [firm name]", "investor brief", "meeting brief", or names a VC/PE firm they're meeting with. Also use when preparing for any fundraising-related meeting, conference, or LP conversation. This skill searches HubSpot for deal history, enriches contacts via Clay, pulls calendar details, and produces a structured brief with firm analysis, attendee profiles, rapport flags (especially shared sports/athletics backgrounds), and pitch customization.

Draft LinkedIn posts and long-form articles in the CEO's voice. Use this skill when the user wants to write a LinkedIn post, draft social content, publish thought leadership, or asks for help with a post. Triggers on "LinkedIn post", "draft a post", "write a post about", "social content", "thought leadership", or when the user shares a Slack thread, internal win, news article, or raw idea and wants it turned into external content. Applies a codified editorial style guide with specific voice rules, formatting conventions, and content patterns.

Write internal memos in the CEO's voice and preferred format. Use this skill when the user asks for a memo, strategy doc, decision doc, process doc, analysis, or any internal written deliverable. Triggers on "write a memo", "draft a memo", "strategy memo", "decision memo", "process memo", "analysis memo", or when another chief-* skill needs to produce a written memo output. Always delivers as markdown (.md) files without horizontal rules between sections.

Org intelligence — parse org charts and headcount rosters into structured context on people, roles, reporting lines, departments, and tenure. Tracks extended teams (contractors, agencies) separately from headcount. Proposes Notion sync after updates. Use this skill when the user asks "who owns X", "who reports to Y", "show me the org", "how big is the engineering team", "who started recently", or provides an org chart image or headcount spreadsheet to ingest. Also use when any chief-* skill needs people context.

Analyze team performance and tool adoption data. Use this skill when the user provides usage data (CSV, XLSX, or pasted data), asks about team productivity, tool adoption rates, engineering velocity, or wants a performance analysis memo. Triggers on "analyze this data", "team performance", "adoption analysis", "Claude Code usage", "engineering velocity", or when the user uploads a spreadsheet with usage/performance data. Produces tiered analysis with per-person breakdowns, trend identification, and specific coaching recommendations.

CEO-level pipeline briefing focused on active open deals — stage distribution, deal health, forecast close dates, and weighted pipeline. Use when the user asks about pipeline, forecast, deal status, revenue outlook, quota attainment, deal velocity, "pipeline update", "forecast update", "where are we on revenue", "how's the pipeline", "deal update", or "what's closing this quarter". Scope is deals only — for lead flow, qualification rates, and top-of-funnel analysis use /funnel instead.

Engineering roadmap progress tracker. Maps JIRA throughput to company objectives and key projects. Summarizes by project and by engineer. Quarterly and monthly scope framing, with emphasis on last 1–2 weeks of progress. Use when asked "where are we on the roadmap?", "what shipped this sprint?", "show me eng progress", "what are engineers working on?", "roadmap update", or "engineering throughput". Requires Notion (for roadmap docs + Jira connected source) and Slack MCPs.

Your AI Chief of Staff. Routes requests to specialized skills for investor prep, board materials, memos, deal analysis, LinkedIn content, team performance, competitive intel, fundraising, customer escalations, event planning, brand style guide, and company context management. Use this skill for ANY request that involves CEO-level operations, strategic work, cross-functional coordination, or brand-consistent visual output. If in doubt about which chief-* skill to use, start here.

Brand style guide and design system reference for your company. Provides the color palette, design tokens, typography, component patterns, CSS custom properties, and Tailwind mappings for building any branded UI. Use this skill whenever creating any UI, frontend, website, landing page, dashboard, presentation, document, slide deck, marketing material, or visual asset that should match your brand. Also trigger when the user mentions "brand colors", "style guide", "design tokens", "design system", or asks to build anything that should look on-brand. Integrates with the Figma MCP to pull the latest design tokens from a source file (configured in `chief-context/company.yaml` under `style.figma_file_key`), with a static fallback embedded below. When another chief-* skill or the frontend-design skill produces visual output, this skill is the canonical source for brand consistency.

Pull the latest Claude Usage report from Slack, add it as a new tab to the usage spreadsheet, and run the weekly insights analysis. Use when asked "claude usage", "usage report", "add usage tab", "usage analysis", or "how is the team using claude". Reads the automated weekly canvas from your engineering leadership Slack channel, writes to a Google Sheet, and produces a tiered performance memo.

Build a comprehensive 360-degree view of a customer by searching all connected services — CRM (HubSpot), Slack conversations, Jira tickets, Notion docs, support data (Pylon), error tracking (Sentry), email (Gmail), calendar meetings, and the web. Use this skill whenever the user wants to understand the full picture of a customer relationship, investigate what led to an escalation, prep for an executive call, review account health, or asks things like "what's going on with [customer]?", "pull everything on [customer]", "customer deep dive", "customer 360", "interaction history", or "what do we know about [customer]?". This is the go-to skill for any request that involves looking across multiple sources to understand a customer's situation holistically.

Lead funnel analysis — lead volume by source, lead-to-qualified conversion, and qualified-to-deal conversion. Use when the user asks about lead flow, lead conversion, funnel velocity, top-of-funnel health, lead quality, lead sources, qualification rate, or wants to compare funnel performance across time periods.

Create professional diagrams in FigJam using Mermaid.js. Applies brand colors from your style guide automatically. Use when the user asks to diagram, visualize, map, or draw — processes, workflows, architectures, user flows, state machines, timelines, decision trees, or any system or concept that benefits from a visual. Triggers on "draw", "diagram", "whiteboard", "visualize", "flowchart", "map out", "sequence diagram", "show me how X works", or "create a diagram".