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.

Try Charlie freeSee what Charlie can do ↓
Charlie
Online · 24/7
LIVE
How much did I make last month?
$11,840 in March — up 18% from February. You sent 19 invoices, all paid, average 3.2 days to pay.
Top customer: Meadowbrook HOA ($2,450). Want the full breakdown?
Show breakdown
Compare to Q4
Text me a copy
Just now: Sent gentle nudge to Henderson Co. — 4 days overdue. I'll check back Tuesday.
Ask Charlie anything…
24/7
Always working — never takes a day off
3×
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.

01
You work
Focus on your jobs. Send invoices when you’re done. Snap receipts when you buy materials.
02
Charlie handles the back office
Chases late payments, categorizes expenses, answers calls, and keeps your books organized.
03
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-up
Manual or basic reminders
Expense categorization
Not included
Voice receptionist
Separate vendor required
Tax prep
Not included
Weekly digest
Not available
AI cost $99+
vs
Maple Street
Charlie AI — included
AI cost
$0 — included free
Invoice follow-up
Auto-chase with escalation
Expense categorization
AI-powered from receipts
Voice receptionist
Built-in (Boss plan)
Tax prep
Schedule C + quarterly estimates
Weekly digest
Every Monday, automatically
AI cost $0
Questions

Common questions.

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.
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.
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.
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.
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 →