AI-Powered Proposal Generator

Overview

An AI-powered tool to automate proposal generation for ^[1], eliminating the manual effort of populating a standard 5-page proposal template. The tool is designed to be conversational: Aaron answers a few targeted questions, the AI populates the template, and Aaron reviews and sends the result directly from HubSpot.

This project was scoped during the ^[2].

Problem

AviaryAI's proposals follow a standard 5-page template, but each one requires manual effort to populate. Aaron must fill in highlighted fields throughout the document, which is repetitive and time-consuming. The goal is to automate this process so Aaron can generate a polished, ready-to-send proposal in minutes rather than manually drafting each one.

Proposed Workflow

Aaron answers questions — The tool prompts Aaron for the key details needed to complete the proposal (client name, use case, pricing, etc.).
AI populates the template — The AI uses Aaron's answers to fill in all highlighted fields in the standard 5-page template.
Aaron reviews — Aaron reviews the generated proposal, requests adjustments if needed ("more of this, less of that").
Send from HubSpot — The final proposal is sent directly from HubSpot, keeping all activity logged in one place.

Requirements

Template source: Aaron will provide the annotated 5-page proposal template with comments on each highlighted field explaining what it means and what information is needed.
Question design: Mark will derive the intake questions from Aaron's annotated template — the questions should map directly to the fields that need to be filled.
HubSpot integration: The final output should be sendable from HubSpot to maintain Blessing's visibility into all outbound activity.
Iterative review: Aaron should be able to request revisions before sending (e.g., adjust tone, add/remove content in specific sections).

Key Decisions

Decision	Rationale
Use a conversational AI intake rather than a form	More natural for Aaron; allows for nuanced answers that map to complex template fields
Build around the existing 5-page template	Avoids redesigning the proposal process; standardizes output while reducing manual effort
Send from HubSpot	Keeps Blessing's visibility intact; all proposal activity stays in the CRM activity feed

Action Items

[ ] Aaron Grossman — Send the annotated proposal template to Mark with comments on each highlighted field explaining what information is needed (due EOD Feb 19, 2026)
[ ] Mark Hope — Review the annotated template, derive intake questions, and build the AI proposal tool

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