billing-automation

Billing Automation

Master automated billing systems including recurring billing, invoice generation, dunning management, proration, and tax calculation.

When to Use This Skill

• Implementing SaaS subscription billing
• Automating invoice generation and delivery
• Managing failed payment recovery (dunning)
• Calculating prorated charges for plan changes
• Handling sales tax, VAT, and GST
• Processing usage-based billing
• Managing billing cycles and renewals

Core Concepts

1. Billing Cycles

Common Intervals:

• Monthly (most common for SaaS)
• Annual (discounted long-term)
• Quarterly
• Weekly
• Custom (usage-based, per-seat)

2. Subscription States

trial → active → past_due → canceled
              → paused → resumed

3. Dunning Management

Automated process to recover failed payments through:

• Retry schedules
• Customer notifications
• Grace periods
• Account restrictions

4. Proration

Adjusting charges when:

• Upgrading/downgrading mid-cycle
• Adding/removing seats
• Changing billing frequency

Quick Start

from billing import BillingEngine, Subscription

# Initialize billing engine
billing = BillingEngine()

# Create subscription
subscription = billing.create_subscription(
    customer_id="cus_123",
    plan_id="plan_pro_monthly",
    billing_cycle_anchor=datetime.now(),
    trial_days=14
)

# Process billing cycle
billing.process_billing_cycle(subscription.id)

Subscription Lifecycle Management

from datetime import datetime, timedelta
from enum import Enum

class SubscriptionStatus(Enum):
    TRIAL = "trial"
    ACTIVE = "active"
    PAST_DUE = "past_due"
    CANCELED = "canceled"
    PAUSED = "paused"

class Subscription:
    def __init__(self, customer_id, plan, billing_cycle_day=None):
        self.id = generate_id()
        self.customer_id = customer_id
        self.plan = plan
        self.status = SubscriptionStatus.TRIAL
        self.current_period_start = datetime.now()
        self.current_period_end = self.current_period_start + timedelta(days=plan.trial_days or 30)
        self.billing_cycle_day = billing_cycle_day or self.current_period_start.day
        self.trial_end = datetime.now() + timedelta(days=plan.trial_days) if plan.trial_days else None

    def start_trial(self, trial_days):
        """Start trial period."""
        self.status = SubscriptionStatus.TRIAL
        self.trial_end = datetime.now() + timedelta(days=trial_days)
        self.current_period_end = self.trial_end

    def activate(self):
        """Activate subscription after trial or immediately."""
        self.status = SubscriptionStatus.ACTIVE
        self.current_period_start = datetime.now()
        self.current_period_end = self.calculate_next_billing_date()

    def mark_past_due(self):
        """Mark subscription as past due after failed payment."""
        self.status = SubscriptionStatus.PAST_DUE
        # Trigger dunning workflow

    def cancel(self, at_period_end=True):
        """Cancel subscription."""
        if at_period_end:
            self.cancel_at_period_end = True
            # Will cancel when current period ends
        else:
            self.status = SubscriptionStatus.CANCELED
            self.canceled_at = datetime.now()

    def calculate_next_billing_date(self):
        """Calculate next billing date based on interval."""
        if self.plan.interval == 'month':
            return self.current_period_start + timedelta(days=30)
        elif self.plan.interval == 'year':
            return self.current_period_start + timedelta(days=365)
        elif self.plan.interval == 'week':
            return self.current_period_start + timedelta(days=7)

Billing Cycle Processing

class BillingEngine:
    def process_billing_cycle(self, subscription_id):
        """Process billing for a subscription."""
        subscription = self.get_subscription(subscription_id)

        # Check if billing is due
        if datetime.now() < subscription.current_period_end:
            return

        # Generate invoice
        invoice = self.generate_invoice(subscription)

        # Attempt payment
        payment_result = self.charge_customer(
            subscription.customer_id,
            invoice.total
        )

        if payment_result.success:
            # Payment successful
            invoice.mark_paid()
            subscription.advance_billing_period()
            self.send_invoice(invoice)
        else:
            # Payment failed
            subscription.mark_past_due()
            self.start_dunning_process(subscription, invoice)

    def generate_invoice(self, subscription):
        """Generate invoice for billing period."""
        invoice = Invoice(
            customer_id=subscription.customer_id,
            subscription_id=subscription.id,
            period_start=subscription.current_period_start,
            period_end=subscription.current_period_end
        )

        # Add subscription line item
        invoice.add_line_item(
            description=subscription.plan.name,
            amount=subscription.plan.amount,
            quantity=subscription.quantity or 1
        )

        # Add usage-based charges if applicable
        if subscription.has_usage_billing:
            usage_charges = self.calculate_usage_charges(subscription)
            invoice.add_line_item(
                description="Usage charges",
                amount=usage_charges
            )

        # Calculate tax
        tax = self.calculate_tax(invoice.subtotal, subscription.customer)
        invoice.tax = tax

        invoice.finalize()
        return invoice

    def charge_customer(self, customer_id, amount):
        """Charge customer using saved payment method."""
        customer = self.get_customer(customer_id)

        try:
            # Charge using payment processor
            charge = stripe.Charge.create(
                customer=customer.stripe_id,
                amount=int(amount * 100),  # Convert to cents
                currency='usd'
            )

            return PaymentResult(success=True, transaction_id=charge.id)
        except stripe.error.CardError as e:
            return PaymentResult(success=False, error=str(e))

Dunning Management

class DunningManager:
    """Manage failed payment recovery."""

    def __init__(self):
        self.retry_schedule = [
            {'days': 3, 'email_template': 'payment_failed_first'},
            {'days': 7, 'email_template': 'payment_failed_reminder'},
            {'days': 14, 'email_template': 'payment_failed_final'}
        ]

    def start_dunning_process(self, subscription, invoice):
        """Start dunning process for failed payment."""
        dunning_attempt = DunningAttempt(
            subscription_id=subscription.id,
            invoice_id=invoice.id,
            attempt_number=1,
            next_retry=datetime.now() + timedelta(days=3)
        )

        # Send initial failure notification
        self.send_dunning_email(subscription, 'payment_failed_first')

        # Schedule retries
        self.schedule_retries(dunning_attempt)

    def retry_payment(self, dunning_attempt):
        """Retry failed payment."""
        subscription = self.get_subscription(dunning_attempt.subscription_id)
        invoice = self.get_invoice(dunning_attempt.invoice_id)

        # Attempt payment again
        result = self.charge_customer(subscription.customer_id, invoice.total)

        if result.success:
            # Payment succeeded
            invoice.mark_paid()
            subscription.status = SubscriptionStatus.ACTIVE
            self.send_dunning_email(subscription, 'payment_recovered')
            dunning_attempt.mark_resolved()
        else:
            # Still failing
            dunning_attempt.attempt_number += 1

            if dunning_attempt.attempt_number < len(self.retry_schedule):
                # Schedule next retry
                next_retry_config = self.retry_schedule[dunning_attempt.attempt_number]
                dunning_attempt.next_retry = datetime.now() + timedelta(days=next_retry_config['days'])
                self.send_dunning_email(subscription, next_retry_config['email_template'])
            else:
                # Exhausted retries, cancel subscription
                subscription.cancel(at_period_end=False)
                self.send_dunning_email(subscription, 'subscription_canceled')

    def send_dunning_email(self, subscription, template):
        """Send dunning notification to customer."""
        customer = self.get_customer(subscription.customer_id)

        email_content = self.render_template(template, {
            'customer_name': customer.name,
            'amount_due': subscription.plan.amount,
            'update_payment_url': f"https://app.example.com/billing"
        })

        send_email(
            to=customer.email,
            subject=email_content['subject'],
            body=email_content['body']
        )

Proration

class ProrationCalculator:
    """Calculate prorated charges for plan changes."""

    @staticmethod
    def calculate_proration(old_plan, new_plan, period_start, period_end, change_date):
        """Calculate proration for plan change."""
        # Days in current period
        total_days = (period_end - period_start).days

        # Days used on old plan
        days_used = (change_date - period_start).days

        # Days remaining on new plan
        days_remaining = (period_end - change_date).days

        # Calculate prorated amounts
        unused_amount = (old_plan.amount / total_days) * days_remaining
        new_plan_amount = (new_plan.amount / total_days) * days_remaining

        # Net charge/credit
        proration = new_plan_amount - unused_amount

        return {
            'old_plan_credit': -unused_amount,
            'new_plan_charge': new_plan_amount,
            'net_proration': proration,
            'days_used': days_used,
            'da

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