AI Accounts Receivable Software for Small Businesses
PaymentPilot is the AI Collections Command Center. Turn unpaid invoices into more predictable cash flow. See what needs attention, understand what should happen next, and manage customer follow-up without losing control of the relationship.
Invoice #1048 is past due and has not received a recent follow-up. PaymentPilot has prepared the next recommended action for review.
Centralize invoice activity, customer communications, promises to pay, disputes and collection tasks in one place.
Your receivables should tell you what needs attention.
PaymentPilot turns scattered invoices, follow-ups and customer activity into a prioritized collections workflow.
Priority Accounts
Quickly identify customers and invoices that deserve attention instead of working through an endless spreadsheet.
AI Recommendations
Get suggested next actions and follow-up guidance based on the account’s current collection situation.
Email Follow-Up
Connect Gmail or Outlook and manage collection communication from the same system where you manage receivables.
Human Approval
AI can assist with the work, but you remain in control of customer communications and collection decisions.
Invoice Management
Organize invoices, balances, aging information and customer details without jumping between disconnected systems.
Collection Timeline
Maintain visibility into communications, tasks, promises to pay, disputes and previous collection activity.
From overdue invoice to clear next action.
PaymentPilot helps your team focus on the accounts most likely to require attention while keeping you in control.
Bring in your invoices
Centralize customer and accounts receivable information inside PaymentPilot.
See priorities
Identify aging balances, priority customers and accounts that need follow-up.
Review recommendations
Use AI-assisted recommendations to determine the most appropriate next collection action.
Take action
Review, approve and execute customer follow-up while maintaining a documented account history.
Automation shouldn’t mean surrendering control.
Collections affect your customer relationships. That’s why PaymentPilot is designed around AI assistance rather than uncontrolled autonomous communication.
The system can help identify risk, prioritize accounts and recommend actions—but important communications remain visible to you.
Start Free — No Credit Card Required →You stay in the driver’s seat.
If unpaid invoices hurt your cash flow, PaymentPilot was built for you.
Move beyond spreadsheets and disconnected inboxes.
Spreadsheets can store balances, but they do not tell your team what deserves attention or preserve the complete collection story.
| Capability | Spreadsheet Workflow | PaymentPilot |
|---|---|---|
| Invoice organization | Manual rows and updates | Centralized customer and invoice records |
| Account prioritization | Manually sort aging data | AI-assisted priority recommendations |
| Follow-up preparation | Write every message manually | Suggested next collection actions |
| Communication history | Scattered across inboxes and notes | Organized collection timeline |
| Customer oversight | Fully manual process | AI assistance with human review |
| Email workflow | Separate from receivable records | Gmail and Outlook integration |
Measure the receivables problems affecting your cash flow.
Evaluate collection speed, identify aging balances and estimate the financial impact of late customer payments. No account is required.
Free DSO Calculator
Calculate Days Sales Outstanding and estimate how long it takes your business to convert credit sales into cash.
Calculate Your DSO →Accounts Receivable Aging Calculator
Break receivables into current, 1–30, 31–60, 61–90 and 90-plus-day buckets to see where collection risk is building.
Analyze Your Receivables →Late Payment Cost Calculator
Estimate how much overdue payments may cost through financing, administrative collection work and tied-up working capital.
Calculate Late-Payment Costs →Your calculations identify the problem. PaymentPilot helps you organize the follow-up.
Start Your 14-Day Free Trial →Start improving your receivables without a major software commitment.
Use PaymentPilot free for 14 days with no credit card required. Continue after your trial for $99 per month.
- 14-day free trial with no credit card required
- Accounts receivable command center
- AI-assisted collection prioritization
- Recommended next actions
- Customer and invoice management
- Gmail or Outlook integration
- Human approval and oversight
Start Free — No Credit Card Required →
Explore our business resources and tools
Visit the Island Insurance Group Resources Center for business risk guidance, insurance tools, educational content and additional resources designed to help business owners make more informed decisions.
Questions about accounts receivable software and PaymentPilot
Understand where PaymentPilot fits in your collection workflow before starting your free trial.
What is accounts receivable collections software?
Accounts receivable collections software helps businesses organize open invoices, identify overdue balances, document follow-up activity and manage the work involved in collecting customer payments.
Is PaymentPilot designed for small businesses?
Yes. PaymentPilot is built for small businesses and service teams that need a clearer, more consistent way to manage outstanding invoices without implementing a large enterprise collections platform.
Does PaymentPilot replace accounting software?
PaymentPilot is designed to support the accounts receivable collection workflow. It does not replace the bookkeeping, financial reporting or tax functions of your accounting system.
How does PaymentPilot use AI?
PaymentPilot uses AI assistance to help analyze receivable activity, identify priorities and recommend possible next actions. Users should review recommendations before acting on them.
Does PaymentPilot send collection messages without approval?
PaymentPilot is designed around human oversight. Important customer-facing communication remains visible for review so the user retains control of collection decisions and customer relationships.
Can PaymentPilot connect to Gmail or Outlook?
PaymentPilot supports Gmail and Outlook integration so collection communication can be managed alongside customer and invoice activity.
What can I measure with the free calculators?
You can calculate Days Sales Outstanding, analyze receivable balances by aging bucket and estimate the potential financing and administrative cost of late customer payments.
How much does PaymentPilot cost?
PaymentPilot includes a 14-day free trial with no credit card required. Continued access after the trial is $99 per month, based on the pricing displayed on this page.
Stop wondering which invoice you should chase next.
See what needs attention. Know what happens next. Stay in control with PaymentPilot.
No credit card required to start your 14-day trial.
Samuel Bennett, Licensed Insurance Agent
sam@islandinsurancegroup.com | 954-804-8144
PaymentPilot is a business software platform designed to assist with accounts receivable management and collection workflows. AI-generated recommendations should be reviewed by the user before action is taken.