AI-Powered

Meet Charlie — your AI
business assistant.

A bookkeeper, collections agent, and business advisor that works 24/7 — included free with every Maple Street plan. No extra cost. No extra apps.

24/7
Always working Never takes a day off
3x
Faster invoice collection with auto-chase
$0
Extra cost Included free on all plans
AI capabilities

Everything Charlie can do for you

Six powerful features working behind the scenes while you focus on your trade.

🤖

Auto-chase overdue invoices

Charlie sends payment reminders on your schedule. Starts polite, escalates the tone over time. You set the rules — Charlie follows through so you don’t have to chase anyone.

📊

Expense categorization

Snap a photo of any receipt. Charlie reads the vendor, amount, and date, then auto-categorizes it — materials, tools, fuel, subcontractors — ready for tax time.

📧

Weekly business digest

Every Monday morning, Charlie sends you a summary: total revenue, outstanding invoices, overdue amounts, and upcoming payments. Know your numbers without opening the app.

💬

Natural language commands

Just tell Charlie what you need. “Send invoice to John for $500” or “How much did I make last month?” Charlie understands plain English and gets it done.

📞

Voice receptionist

Charlie answers your phone 24/7, books jobs, takes messages, and captures lead info. Powered by Retell AI. Never miss a call — even at 2am or when you’re on a ladder.

📋

Tax prep assistant

Charlie tracks every deduction throughout the year, estimates your quarterly taxes, and prepares your Schedule C data. No more scrambling at tax time.

How it works

You work. Charlie handles the rest.

Three steps to a fully automated back office.

1

You work

Focus on your jobs. Send invoices when you’re done. Snap receipts when you buy materials.

2

Charlie handles the back office

Chases late payments, categorizes expenses, answers calls, and keeps your books organized.

3

You get paid faster

Money comes in sooner. Books are always up to date. Tax time is painless.

Comparison

AI that's actually included

Other platforms charge extra for limited AI. Charlie is included on every plan.

Others
AI Add-on
AI cost$49–$99/mo extra
Invoice follow-upManual or basic reminders
Expense categorizationNot included
Voice receptionistSeparate vendor required
Tax prepNot included
Weekly digestNot available
AI cost$99+
VS
Maple Street
Charlie AI — Included
AI cost$0 — included free
Invoice follow-upAuto-chase with escalation
Expense categorizationAI-powered from receipts
Voice receptionistBuilt-in (Boss plan)
Tax prepSchedule C + quarterly estimates
Weekly digestEvery Monday, automatically
AI cost$0
Questions

Common questions

What exactly can Charlie do?
Charlie auto-chases overdue invoices, categorizes expenses from receipt photos, sends weekly business digests, responds to natural language commands (like “send invoice to John for $500”), answers your phone 24/7 as a voice receptionist, and helps with tax prep including quarterly estimates and Schedule C.
Is Charlie included in my plan?
Yes. Charlie’s core features — auto-chase, expense categorization, weekly digest, and natural language commands — are included on all plans, even the free tier. Voice receptionist and advanced automations are available on Business and Boss plans.
Is my business data safe with Charlie?
Absolutely. Charlie runs on Anthropic’s Claude API with enterprise-grade security. Your data is encrypted in transit and at rest, never used to train AI models, and never shared with third parties. Charlie only accesses data within your Maple Street account.
How does the voice receptionist work?
Charlie Voice Agent uses Retell AI to answer incoming calls. It greets callers professionally, captures their name and job details, books appointments based on your availability, and sends you a summary via text. Available on Boss plan.
Can Charlie really replace a bookkeeper?
For most solo contractors and small teams, yes. Charlie auto-records every invoice and payment, categorizes expenses, generates profit and loss statements, and prepares Schedule C data. If you need a CPA for complex tax situations, Charlie’s organized records make their job faster and cheaper.

Let Charlie handle
the busywork.

Stop chasing invoices. Stop sorting receipts. Stop doing your own books.
Charlie does it all — included free.

Get started free →