Estimate & Proposal Automation

Close Faster. Write Less.

Writing proposals takes hours you don't have. I build systems that generate polished, branded proposals in minutes -- and follow up automatically when they go unread.

Book a Free Strategy Session

Or email chuck@startuptosold.com

2hrs

Average time spent writing a proposal manually -- I get it to minutes

60%

Of proposals are never followed up on after the first send

Proposals a month is all it takes for this to pay for itself

How It Works

Three phases. Faster closes, less writing.

I audit your proposal process, build the automation to fit your tools and tone, and keep it tuned as your services and pricing evolve.

Phase 01

Assessment & Build

I review your current proposal process, intake flow, and past proposals to understand your tone and format. Then I build the automation around your existing tools.

Phase 02

Hand-off

I train you on how to trigger the proposal writer, review the draft, and send. You stay in control -- the AI handles the heavy lifting.

Phase 03

Maintenance

Monthly check-ins to update prompts as your services change, review close rates, and refine follow-up timing based on what's working.

What I Build

Every automation in this category.

These are the specific proposal automations I build. The AI proposal writer is the flagship -- but the tracking and follow-up pieces are what actually close the deal.

AI Proposal Writer

Short intake conversation or form → AI pulls from your past proposals and matches your tone and format → polished branded proposal in minutes, delivered as a Google Doc or PandaDoc for your review. You edit, approve, and send. No more starting from scratch.

Auto-Generate Draft Estimates from Intake Data

When a prospect fills out your intake form, their data flows directly into a pre-structured estimate template. You get a draft to review in seconds instead of building it from scratch.

Proposal Tracking & Automated Follow-Up

Know when a proposal is opened, how many times, and by whom. Automated follow-up goes out when a proposal sits unread for 48 hours. No more wondering whether they got it.

Viewed-but-Not-Signed Alert

When a prospect opens a proposal but doesn't sign within a set window, your team gets notified. The right moment to follow up -- when they're clearly thinking about it.

Who It's For

Right for your business if...

Contractors, consultants, agencies, and professional services firms that send proposals regularly. If you write more than five proposals a month, this pays for itself -- and if your close rate is lower than you'd like, automated follow-up alone is often the fix.

You send five or more proposals per month

Writing proposals takes more than an hour of your time each

You've lost deals simply because you didn't follow up fast enough

Questions

What to know before we talk.

Yes -- the AI is trained on your past proposals and calibrated to your tone. The output won't be identical to something you'd write, but it'll be close enough that a quick edit is all you need. Quality improves as the system sees more of your proposals.

Always. This is human-in-the-loop by design. You review, edit if needed, and approve before anything is sent to a client. The AI drafts; you decide.

Proposal view tracking requires a tool like PandaDoc or HubSpot. For the AI writer, I work with whatever you use for intake -- a form, your CRM, or a simple conversation. I'll map this out during the assessment.

Every engagement starts with an Assessment. Proposal automation is medium complexity -- the AI writer requires prompt tuning per client, which is why the assessment matters before I quote a build.

Free Tool

Not sure if your task is automatable?

Describe one repetitive task and get an instant verdict: automatable or not, how it would work, and how many hours you'd save per year. No email required.

Try the Analyzer → Takes 30 seconds

Get Started

Ready to close faster and write less?

Book a free strategy session. I'll look at your current proposal process and tell you exactly what it would take to automate it.

Book a Free Strategy Session

Or email chuck@startuptosold.com