Lendware

Billing Operations Map

Team: 1 Controller, 1 Rep

Tech: Stripe, QuickBooks, HubSpot

What Could Go Wrong

Failure scenarios, mitigations, and preventions

Search Failure Scenarios
Find scenarios by stage, description, or mitigation strategy
13 of 13 scenarios

High Impact

8

Medium Impact

5

Low Impact

0

Signup
2 failure scenarios

Customer pays but account is not provisioned

HIGH
Mitigation:

Krystal monitors payment confirmations in Stripe/QuickBooks daily. If payment received but no account created, manually provision within 1 hour and send apology email with expedited onboarding.

Prevention:

Implement webhook monitoring to alert Slack channel when payment succeeds but no account creation event follows within 5 minutes.

Payment link sent to wrong email address

MEDIUM
Mitigation:

Rep verifies Billing Admin email in HubSpot before sending payment link. If wrong email used, void original link, generate new link, and send to correct address within 2 hours.

Prevention:

Add email confirmation step in HubSpot workflow before payment link generation. Require Rep to confirm Billing Admin email matches deal contact.

Onboarding
1 failure scenarios

Customer does not log in within 7 days (activation gate not met)

MEDIUM
Mitigation:

Rep sends follow-up email on day 7 offering assistance. If no response by day 14, Rep calls customer to troubleshoot login issues or reschedule onboarding.

Prevention:

Implementation team sends reminder email on day 3 with login instructions and troubleshooting guide. Krystal monitors PostHog activation events daily.

Expansion
2 failure scenarios

Customer adds users without notifying Lendware (unreported seat additions)

HIGH
Mitigation:

Tim monitors 'upgrade' Slack channel daily and tags account manager or Krystal when new user detected. Rep contacts customer within 24 hours to confirm seat addition and send prorated invoice.

Prevention:

Update contract language to state that adding a seat constitutes an annual commitment. Krystal conducts weekly seat count verification in PostHog vs. billing system. Implement in-app notification when customer adds user.

Proration calculated incorrectly (double billing or undercharging)

HIGH
Mitigation:

Krystal reviews all prorated invoices before sending to customer. If error detected, void incorrect invoice, generate corrected invoice, and send explanation email to customer.

Prevention:

Implement automated proration calculator with manual review step. Document proration formula in billing system notes. Require Krystal approval for all mid-cycle charges over $500.

Contraction
1 failure scenarios

Seat reduction applied mid-cycle instead of at renewal (refund liability)

HIGH
Mitigation:

If reduction applied incorrectly, do NOT issue refund. Explain to customer that reduction takes effect at renewal per contract terms. Document error in HubSpot ticket and add reminder for renewal date.

Prevention:

Add 'scheduled reduction' field in billing system that only applies changes on renewal date. Rep must document scheduled reductions in both billing system and HubSpot with renewal date noted.

Renewal
2 failure scenarios

60-day renewal reminder not sent (legal liability and refund risk)

HIGH
Mitigation:

If reminder missed, send immediately with apology. If customer disputes renewal, Lendware may be liable for refund due to failure to meet contractual obligation. Document proof of sending for all future renewals.

Prevention:

Implement automated renewal reminder workflow in HubSpot that triggers 60 days before renewal. Rep must log proof of sending (email sent timestamp) in HubSpot ticket. Krystal reviews reminder log weekly.

Annually-paid customer invoice not sent 30 days before renewal

MEDIUM
Mitigation:

If invoice missed, send immediately. If customer cannot pay within remaining time, offer payment plan or extend grace period. Document agreement in HubSpot ticket.

Prevention:

Krystal sets calendar reminder 35 days before renewal for all annually-paid customers. Implement automated invoice generation workflow in QuickBooks/Stripe.

Churn
1 failure scenarios

Support team cancels subscription directly without using churn channel

HIGH
Mitigation:

Support team has no access to Stripe/QuickBooks, so this scenario is prevented by access control. If access granted in future, implement mandatory churn channel workflow.

Prevention:

Maintain current access control policy. Support team must use churn Slack channel for all cancellation requests. Claudio/Krystal are only users with billing system cancellation permissions.

Collections
2 failure scenarios

Payment fails but dunning emails not sent (customer unaware of issue)

MEDIUM
Mitigation:

If dunning emails missed, Rep sends personalized email immediately explaining payment failure and retry schedule. Offer to update payment method or switch to ACH.

Prevention:

Verify dunning email templates are active in Stripe/QuickBooks. Rep monitors failed payment dashboard daily and sends manual follow-up if automated email not sent within 24 hours.

Account suspended but customer not notified (surprise access loss)

HIGH
Mitigation:

If suspension occurs without notification, Rep calls customer immediately to explain situation and offer payment options. Restore access temporarily (24-48 hours) while payment is processed.

Prevention:

Support team must send suspension notice email before revoking access via Auth0. Implement 24-hour grace period between suspension notice and access revocation.

Disputes
1 failure scenarios

Chargeback received but no response submitted (automatic loss)

HIGH
Mitigation:

Krystal monitors dispute resolution center in Stripe (legacy) and QuickBooks (new) daily. If dispute received, gather evidence (contract, renewal reminder proof, usage logs) and respond within 7 days.

Prevention:

Set up email alerts for new disputes. Krystal checks dispute dashboard every Monday and Thursday. Maintain organized records of all customer communications (renewal reminders, invoices, confirmations) for dispute evidence.

Exceptions
1 failure scenarios

Special pricing or one-off invoice created without documentation

MEDIUM
Mitigation:

If exception created without documentation, Rep must retroactively document in HubSpot ticket with reason, approval timestamp, and Krystal confirmation. Send confirmation email to customer.

Prevention:

Require HubSpot ticket for all exceptions. Rep must document reason, get Krystal approval via ticket comment, and attach approval screenshot before executing change in billing system.

General Best Practices

Proactive Monitoring

  • • Krystal checks Stripe/QuickBooks payment dashboard daily
  • • Tim monitors "upgrade" Slack channel for unreported user additions
  • • Krystal monitors dispute resolution center Monday and Thursday
  • • Rep reviews failed payment dashboard daily for dunning follow-ups
  • • Krystal conducts weekly seat count verification (PostHog vs. billing system)

Documentation Requirements

  • • All billing changes must have HubSpot ticket with timestamp and actor
  • • Renewal reminders must be logged with proof of sending
  • • Exceptions require Krystal approval documented in ticket comment
  • • Scheduled reductions must be noted in both billing system and HubSpot
  • • Maintain organized records for dispute evidence (contracts, emails, usage logs)