Proposal Automator

Generate professional 7-section client proposals with three pricing packages, CRM personalization, and a SOW-ready brief file -- from a conversation or an existing brief.

Overview

The Proposal Automator produces complete client proposals in Markdown format with a proven 7-section structure: Cover Letter, Executive Summary, Understanding & Approach, Scope of Work, Timeline & Milestones, Pricing (three packages), and Terms & Conditions. Every proposal also generates a companion SOW-compatible brief file, ready for handoff to the SOW Generator.

Two commands serve different starting points. Use create when you are starting from scratch -- it walks you through an interactive brief collection or accepts a brief file. Use from-brief when you already have a brief document (local file or Notion page) and want to generate the proposal directly from it.

When your Notion CRM is connected, the system enriches proposals with client context: past project history, relationship details, industry information, and known preferences. This context shapes the Cover Letter, informs the Understanding & Approach section, and helps calibrate pricing to what the client has invested before. Completed proposals are tracked in the Founder OS HQ - Deliverables database with Type = "Proposal", and Company/Deal relations are set automatically when a CRM match exists.

Required Tools

Tool	Required	Purpose
Filesystem	Yes	Write proposal and brief files to the output directory
Notion CLI	No	CRM context enrichment and proposal tracking in HQ Deliverables

Commands

`/founder-os:proposal:create`

What it does -- Generates a complete professional proposal through an interactive workflow. Resolves client context from your CRM, collects the project brief (interactively or from a file), generates all seven sections with three pricing packages, saves the proposal and a SOW-compatible brief file, and records the result in Notion.

Usage:

/founder-os:proposal:create [client] [--output=PATH] [--brief=FILE]

Example scenario:

A prospect asks for a proposal for a new customer portal. Run /founder-os:proposal:create "Acme Corp" and you are walked through five questions: project description, key deliverables, target timeline, budget range, and special requirements. The system pulls Acme's history from your CRM, generates a personalized cover letter referencing your past work together, scopes three packages (Foundation at $18K, Growth at $30K, Transformation at $45K), and saves both the proposal and a brief file. The whole process takes about two minutes.

What you get back:

Two Markdown files saved to your output directory: the complete 7-section proposal (proposal-acme-corp-2026-03-19.md) and a SOW-compatible brief (brief-acme-corp-2026-03-19.md). The output summary shows the client name, file paths, Notion status, and a package comparison table with scope, timeline, and pricing for all three tiers. The recommended package is highlighted.

Flags:

--output=PATH -- Output directory (default: ./proposals/)
--brief=FILE -- Use an existing brief file instead of interactive collection

`/founder-os:proposal:from-brief`

What it does -- Generates a complete proposal from an existing brief document. Accepts a local Markdown or text file, or a Notion page URL. Extracts the client name, project description, deliverables, constraints, and special requirements from the brief, then generates the full 7-section proposal with three pricing packages. Gaps in the brief are marked for review rather than blocking generation.

Usage:

/founder-os:proposal:from-brief [file-or-url] [--client=NAME] [--output=PATH]

Example scenario:

After a discovery call, you typed up meeting notes in a Markdown file with the client's requirements. Run /founder-os:proposal:from-brief meeting-notes.md --client="TechStart" and the system extracts the project details from your notes, resolves TechStart's CRM context, and generates a polished proposal. Any information that could not be extracted from the notes is flagged with review comments so you know exactly what to fill in.

What you get back:

The same two-file output as create: a complete proposal and a SOW-compatible brief. If the brief was missing key information (no budget range, unclear deliverables), those sections include  markers and the output summary notes what was missing.

Flags:

--client=NAME -- Override the client name extracted from the brief
--output=PATH -- Output directory (default: ./proposals/)

The 7-Section Proposal Structure

Section	Purpose	Key Rules
Cover Letter	Establish rapport with a personalized introduction	References the client's specific situation. Never opens with "Dear Sir/Madam."
Executive Summary	Problem-solution-value at a glance	Under 300 words. A decision-maker should understand the full engagement from this section alone.
Understanding & Approach	Demonstrate comprehension of the client's challenges	Identifies 2-3 underlying problems the client may not have articulated.
Scope of Work	Define deliverables with acceptance criteria	Includes explicit Exclusions and Assumptions subsections.
Timeline & Milestones	Phase breakdown with week numbers	Every deliverable maps to a phase. Client-side dependencies noted explicitly.
Pricing	Three packages with comparison table	Leads with scope, not price. Recommended package is marked.
Terms & Conditions	Payment, IP, change control, confidentiality	Milestone-based payment tied to deliverable acceptance, not dates.

Three-Tier Pricing

Every proposal includes exactly three packages following the good-better-best framework:

Tier	Role	Typical Scope
Starter	Entry point -- solves the core problem	Core deliverables only, shortest timeline, 1 revision round
Professional (Recommended)	Best value-to-scope ratio	Core + key enhancements, standard timeline, 2 revision rounds, 2-week hypercare
Enterprise	Full vision for clients with flexible budgets	Everything + stretch deliverables, extended timeline, unlimited revisions, 4-week hypercare

Packages are named to signal value and fit (e.g., Foundation / Growth / Transformation), not size or price. The comparison table always leads with scope, with investment as the last row.

What Sections Does a Generated Proposal Include?

Every proposal follows a 7-section structure: Cover Letter, Executive Summary, Understanding & Approach, Scope of Work, Timeline & Milestones, Pricing (three packages), and Terms & Conditions. Each section follows specific rules -- the Executive Summary stays under 300 words, the Scope includes Exclusions and Assumptions subsections, and the Pricing section leads with scope rather than price. A companion SOW-compatible brief file is also generated.

Tips & Patterns

Start with create for new prospects where you need to gather requirements interactively. Use from-brief when you already have notes or a scope document.
Set up business context files (_infrastructure/context/active/business-info.md) to automatically include your company name, service descriptions, and standard terms in every proposal.
The SOW brief file is a direct input to /founder-os:sow:from-brief. After the client selects a package, generate the SOW in one command.
CRM context makes a visible difference in proposal quality. When your Notion CRM has the client's industry, past projects, and relationship history, the Cover Letter and Understanding & Approach sections reference real details instead of generic language.
Proposals are tracked in Notion with status "Draft" and the selected package defaults to "None". Update the record when the client makes a decision.

Contract -- After a proposal is accepted and a contract is signed, use Contract Analyzer to review the final agreement against your proposed terms.
Invoice -- The pricing and payment terms in your proposal define what invoices should look like. Process invoices against the same client in the Finance database to maintain end-to-end visibility.
Health -- Active proposals contribute to the relationship context that health scoring uses. A client with a pending proposal is a client worth monitoring.