Proposal Automation: Two-Phase Implementation Plan

Overview

The current proposal workflow — Excel budget → Word document → PDF → email via Outlook — happens entirely outside Salesforce. This prevents any automated reporting on bid volume or dollar value, which leadership (Jim) has explicitly requested. A two-phase plan bridges the gap: Phase 1 delivers reporting capability immediately without disrupting existing habits; Phase 2 migrates the full workflow natively into Salesforce with AI-assisted document generation.

Related: ^[1] · ^[2] · ^[3]

Current State (Problem)

• Estimators receive drawings/takeoffs and develop budgets in Excel (multiple templates depending on project type: install, architectural, digital fabrication/fine art)
• Proposals are written in Word from a template stored in the server's prospect folder, then saved as PDF
• PDFs are sent via Outlook — not logged in Salesforce
• No consistent file naming convention; version control relies on date-stamped filenames (not always followed)
• Opportunity records in Salesforce are not reliably updated with proposal value or send date
• Result: generating a report of "monthly bids sent and total dollar value" requires a fully manual, analog process

Phase 1: Immediate Automation (Server-Side PDF Watcher)

Goal: Enable proposal reporting in Salesforce without changing how proposals are created.

How It Works

1. A "Sent" folder is created on the existing file server
2. When a proposal PDF is finalized and sent to the client, the sales rep drags it into the Sent folder (one additional step)
3. A server-side script monitors the Sent folder for new files
4. On detecting a new PDF, the script:
   - Parses the document to extract proposal value and relevant metadata
   - Automatically updates the corresponding Salesforce Opportunity record with the proposal amount and submission date
5. No manual Salesforce entry required from the rep

Why This Works Now

• Zero change to the proposal creation process
• Provides the data Jim needs (monthly bid count + dollar value) almost immediately
• The Sent folder also solves the version-control problem: whatever is in Sent is definitively what went to the client
• Adoption can be enforced operationally (e.g., commission tracking tied to Sent folder presence)

Prerequisites & Open Items

• [ ] Lincoln to send proposal templates and budget Excel templates to Mark and Karly
• [ ] Mark & Karly to build and demo the automation script
• [ ] Mark to coordinate with VEATH for server access and folder creation
• [ ] Mark & Karly to create a Partial Data Sandbox for development and testing before production deployment
• [ ] Lincoln to audit and enforce file naming conventions (no SOP currently exists)

Phase 2: Native Salesforce Solution

Goal: Move proposal creation fully into Salesforce, eliminating the prospect folder as the source of truth.

Components

Custom Estimate Object

• Mirrors the existing Excel budget spreadsheet(s)
• Multiple layouts/record types to match the different budget templates (install, architectural, digital fabrication/fine art)
• User selects project type → relevant fields appear → object calculates totals
• Linked as a child record to the parent Opportunity

Custom Proposal Template Object

• Replaces Word templates stored on the server
• Templates defined per proposal type (one-pager, full contractual proposal, ROM/budgetary, etc.)
• Pulls structured data from the Estimate object

AI Generation Layer

• Salesforce's native document/template tooling produces poor-looking output — a known pain point with CPQ-style workflows
• Instead: pass the Estimate data + proposal rules to an AI layer to generate a polished, well-formatted proposal document
• Output looks hand-crafted, not template-generated; no awkward page breaks or boilerplate artifacts
• AI only references two inputs: the data (Estimate object) and the rules (proposal guidelines), so output is reliable and consistent

Outlook Integration

• Once a proposal is reviewed and approved inside Salesforce, it is sent directly via the integrated Outlook connection
• Send event is automatically logged on the Opportunity record

Prerequisite: Opportunity Stage Optimization

Before building Phase 2, Opportunity Stages must be audited and optimized. Stages drive forecasting, probability weighting, and reporting — they are difficult to restructure after the fact. Lincoln's executive coach's framing is useful here: stages should reflect the client's journey, not internal process steps. Internal operational milestones can exist in other objects (tasks, projects) without cluttering the sales pipeline view.

• [ ] Lincoln to audit current stages and propose an optimized set
• [ ] Review with Mark and Karly before any Phase 2 build begins

Phasing Rationale

Phase 1 is not the end state — it is a bridge that satisfies the immediate reporting requirement while Phase 2 is designed and built properly.

Action Items