Meet your chief of staff, Charlie Chat | AI help that truly cares about your business

Meet your chief of staff, Charlie Chat

AI that saves you money and gives you back your time.
💬 Drafts in your voice✋ Nothing sends without you🔓 No long-term contract
Charlie Chat avatarCharlie Chat with his tablet
Charlie Chat

Systemize your business to get back your time.

Charlie Chat is the system. He helps you build it, then helps you run it.

  • Strategize with Charlie Chat to build standard office procedures for your company (SOP)
  • Build systems and processes you can use in ChatGPT and your other tools
  • Create email campaigns
  • Draft contracts for your review
  • Project planning

Nothing goes out without your approval.

We know how full your plate is.

Late night emails, a quote you meant to follow up on, a call you couldn't take because you were on with a customer. That isn't a work harder problem. That just needs a system that has your back. That's what we build together.

Let Charlie Chat free up your time.

Why we do this: to be of service

Jackie Connolly
Jackie Connolly, founder
Jackie shaking hands with a happy small-business owner

We truly care

We listen first, learn how your business really runs, and only recommend what will help.

Jackie working with a client at a laptop
🤝

We do it with you

Live setup, real training, and plain answers. You are never left to figure it out alone.

Jackie Connolly with Charlie Chat
📈

Your business, better

Fewer missed leads, calmer days, happier customers. That's how we measure success.

Charlie Chat in a blue suit holding a tablet

What Charlie Chat does for you every day

🌅

Morning brief

What's on, who's waiting, and what needs you first.

🌙

End-of-day wrap-up

What's done, what's left, and what's first tomorrow.

📬

Email flagging

New leads, payments due, and cancellations rise to the top.

✍️

Drafts in your voice

Replies, estimates, and review responses, ready for your OK.

⭐

The Golden Rule: Charlie Chat drafts, you approve.

Nothing is ever sent, posted, or scheduled without your OK. You stay the boss. You simply gain the staff.

Three clear ways to start. No surprises.

Each step includes everything in the one before it. Start where you are and grow when you're ready.

Charlie Chat beside a laptop, ready to work on it with you

Charlie Chat Setup

Tier one runs in ChatGPT, Chief of Staff, Charlie Chat, $399.

$399 one time · no monthly fee
  • Your own Charlie Chat, set up live inside ChatGPT
  • Morning brief
  • End-of-day wrap-up
  • Email flagging
  • Three business projects
  • Crew training on the call
  • One week of support
  • No CRM, phone system, or automation
➕ In-person setup: add $199

Lead Catcher

Tier two, high level starter build, Lead Catcher, $2,500, $149 a month.

$2,500 + $149/mo
  • Your phone gets answered
  • AI receptionist / missed-call attendant
  • Business phone number
  • Missed-call text-back
  • New-lead and quote follow-ups
  • Google review requests
  • One lead capture page
  • A2P texting registration
  • One 60-minute training
  • 30 days of launch support
  • Not included: custom knowledge base, Facebook/Google integrations, no-show or past-customer campaigns, reporting
⏱ Live in 7–10 days · Pay in full or $1,250 + $1,250

AI Front Office

Tier three, most complete, AI Front Office, $5,000 plus $149 monthly fee.

$5,000 + $149/mo
  • Everything in Lead Catcher, plus:
  • Your phone gets answered
  • Your inbox gets cleared
  • Your calendar gets filled
  • AI chat agent
  • Custom knowledge base
  • Full funnel
  • Full integration with most of your current tools: Facebook, Instagram, Google Business, your website chat, email (Gmail or Outlook), and calendar (Google or Outlook), all in one inbox. Plus lead sources for your industry, like Zillow, Realtor.com, Angi, or Thumbtack, and Stripe payments.
  • Four follow-up sequences: new lead, quote, no-show, past customer (text + email)
  • Reporting
  • Recorded training videos
  • 30 days of launch support
⏱ Live in 7–14 days · $2,500 to start, $2,500 at launch

Good to know

  • Charlie Chat ($399) is ChatGPT-based. The full HighLevel builds include the CRM, automations, and phone and text follow-up.
  • Your $399 counts. It credits toward Lead Catcher or AI Front Office if you upgrade within 30 days.
  • Grow anytime. Moving from Lead Catcher to AI Front Office is just the $2,500 difference.
  • Not sure which fits? The free Business Diagnostic will tell you, honestly.

What happens after you sign

For Lead Catcher and AI Front Office builds, about 14 workdays from start to fully tuned.

Day 1

Welcome

Your welcome email and onboarding form arrive. We collect logins, logo, services, prices, FAQs, and hours.
Days 2–3

Kickoff call

30 to 45 minutes together to learn your tone, your customers, and what matters most.
Days 4–6

We build

Your account is built from a proven template and A2P texting registration is submitted.
Days 7–8

Quality check

We test every form, text, and follow-up before you ever see it.
Days 9–10

Launch and training

We go live together and train you and your crew.
Days 11–14

Tune and support

We watch, adjust, and answer questions so everything runs smoothly.

** Texting can depend on carrier A2P approval, which is outside of our control. We'll keep you posted every step.

Our platform charges about $0.0075 per text (per 160-character segment, plus the recipient's carrier fee of about half a cent) and about $0.0007 per email sent. These per-text and per-email fees are charged by our platform and passed through; they are not our fee.

Why live, hands-on setup works

🖥️
Charlie Chat

Done together

We share screens and set it up with you, step by step. No 14-hour video course.

📍

Made for your business

Tuned to your town, your real pricing, and your true voice.

A small-business team working together
📱

Your crew included

Your team joins and learns on their own phones.

🔓

You own everything

All accounts, domain rights, and data are yours. No long-term contract.

Questions? Clear answers.

Jackie Connolly and Charlie Chat mapping a business system together
What's the difference between the three options?

Charlie Chat Setup ($399) is a ChatGPT-based assistant for you: briefs, email flagging, and drafts, with no CRM or automation. Lead Catcher ($2,500 + $149/mo) is a HighLevel CRM/system build with an AI receptionist / missed-call attendant that catches and follows up on leads by phone and text. AI Front Office ($5,000 + $149/mo) adds an AI chat agent, a custom knowledge base, full integration with most of your current tools (Facebook, Instagram, Google Business, website chat, email, and calendar), all four follow-up sequences, and reporting. The four are new lead, quote, no-show, and past customer, sent by text and email, and they stop when the contact replies or books.

What's included in the $399 setup?

On a live video call, I set up your own Charlie Chat inside ChatGPT, trained on your services, pricing, and voice. You get the morning brief, end-of-day wrap-up, email flagging, three business projects, and training for you and your crew. One-time fee, no monthly charge, with one week of support.

Does my $399 count if I upgrade?

Yes. It credits toward Lead Catcher or AI Front Office if you upgrade within 30 days.

Are there monthly fees?

Not for the $399 setup. It's one-time, with one week of support. Lead Catcher and AI Front Office each add $149/month for ongoing nurturing and automation management.

How do payments work?

Lead Catcher is paid in full or as $1,250 to start and $1,250 at launch. AI Front Office is $2,500 to start and $2,500 at launch. Moving from Lead Catcher to AI Front Office is the $2,500 difference.

Can you set it up in person instead of online?

Yes. For an extra $199, we come to your office in the South Coast and Dartmouth, MA area, do the setup in person, and train your crew on their own phones.

How quickly can we be up and running?

Charlie Chat is working by the end of our call. Lead Catcher goes live in 7 to 10 days and AI Front Office in 7 to 14 days. Texting depends on carrier A2P approval, which can sometimes take longer.

What if I'm not technical at all?

That's exactly who this is for. We handle the setup while you watch, and you use Charlie Chat with plain commands like "Morning brief."

Could the AI send a customer the wrong price?

Charlie Chat only drafts. Nothing is sent, posted, or scheduled until you review and approve it.

Who owns my accounts and data?

You do. All accounts, domain rights, and data are yours, with no long-term contract.

What is the free Business Diagnostic?

You fill out a short intake form about your business. We review it with care and send back a written report with your bottlenecks, suggested fixes, cost, timeline, and which option fits best, or whether you need none at all.

What happens if something stops working?

Call +1 (508) 258-4953 and we'll help you sort it out. Charlie Chat Setup includes one week of support, and Lead Catcher and AI Front Office include 30 days of launch support, and the $149/month plan on Lead Catcher and AI Front Office covers ongoing nurturing and automation management.

What should I prepare?

A computer with good internet, your email and ChatGPT logins, a list of your services and pricing, your most common customer questions, and your phone. Bring your crew if they'll use Charlie Chat too. Also gather your logo and any photos of yourself you'd like to use in your business.

Is there a training portal?

Yes. Every package, from the $399 Charlie Chat to the $2,500 Lead Catcher and the $5,000 AI Front Office, comes with our open, self-serve training portal. It starts with a suggested video on getting into Settings in ChatGPT and answers the questions clients ask most often, so you can handle the basics anytime before reaching out to support. It's separate from your 60-minute live training (recorded for you) and your short how-to videos, one per system, that you keep.

Let's make your business more automated and productive to save you time and money.

The sooner you automate, the sooner you get your time back.

Start small with Charlie Chat, or let us take a caring, honest look at your business first. Either way, you'll know exactly what you're getting.

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Real people, real AI, working side by side. Get your free business diagnostic.

Have a question? Text or call +1 (508) 258-4953

Your information is kept confidential and used only to help your business.