Cash clarity beats fancy dashboards. This guide shows how to automate receipts, invoicing, reconciliation, and monthly packs—so you know where money goes and close on time.
Table of Contents
- Who This Guide Is For
- Principles (Accurate, Boring, On Time)
- Receipt Capture: Snap, Parse, Attach
- Invoicing: From Signature to Cash
- Reconciliation: Match and Move On
- Vendor Bills & Subscriptions: Control Outflow
- One-Click Monthly Pack (Management Reporting)
- Comparison Table: Manual vs Autopilot Books
- Starter Stacks (Copy & Adapt)
- Implementation Checklist
- 30-Day Plan
- Security & Privacy (Plain English)
- Templates You Can Copy
- FAQs
- Internal Links (add them at the end)
Who This Guide Is For
Entrepreneurs and small teams without a finance department. You’ll set up receipt capture, vendor rules, invoice workflows, payment reminders, reconciliation, and a one-click monthly report. If you also run client onboarding, connect this with Client Onboarding on Autopilot → /automate-client-onboarding.
Principles (Accurate, Boring, On Time)
- Automate the repeatable. Category suggestions, reminders, and exports.
- Lock templates. Invoices and narratives should look the same every month.
- Evidence by default. Receipts + audit trails attached to transactions.
- Separation of duties. Even solo founders can require approval for risky actions.
- Privacy matters. Redact PII; store only what you must.
Receipt Capture: Snap, Parse, Attach
Goal: Every expense has a receipt and category within 48 hours.
Setup
- Mobile app scans → OCR vendor, date, amount, tax.
- Rules: map common merchants to categories/tax codes.
- Owner: you or a VA reviews exceptions weekly.
Quality bar
- ≥95% of expenses with receipt attached.
- <5% category corrections after month 2.
Tips
- Keep one card per business; avoid mixing personal.
- For subscriptions, store the contract/terms in a folder linked from the vendor record.
Invoicing: From Signature to Cash
Goal: Invoice on signature, get paid on time, and keep DSO low.
Workflow
- Client signs → auto-create invoice (amount, due, link).
- Send invoice immediately; attach SOW/PO if required.
- Reminders: 3 days before due, due day, +7 days.
- On payment → post receipt; thank-you note + next milestone.
Best practices
- Offer 2 methods (card + bank transfer).
- Use invoice numbering with date/customer prefix.
- Add late-fee and early-pay policy (clear, consistent).
Metrics
- DSO, % paid on time, collection time by client.
Internal handoff: connect this to your onboarding flow so contracts trigger invoices automatically → /automate-client-onboarding
Reconciliation: Match and Move On
Goal: Bank/GL reconciliation without manual pain.
Quick start
- Connect bank feeds; import last 90 days.
- Use matching rules (amount ± tolerance, memo patterns, vendor name).
- Post only after human approve when confidence < threshold.
Exception handling
- Duplicate alert → check invoice numbers and dates.
- Partial payment → mark as partially paid; schedule balance reminder.
- Unknown vendor → create rule or escalate to owner.
Audit readiness
- Keep reason codes (why matched).
- Export a reconciliation report monthly.
Vendor Bills & Subscriptions: Control Outflow
Goal: Pay on time, catch duplicates, and avoid creep.
Steps
- Centralize bills to one inbox (e.g., bills@yourdomain).
- Detect duplicate invoices (same PO/invoice/amount).
- Tag vendor risk (delivery, quality, exposure).
- Schedule payment runs weekly; use approval for > X €.
Savings
- Negotiate annual billing for discounts.
- Track seat counts; remove unused licenses.
One-Click Monthly Pack (Management Reporting)
Goal: Generate a consistent pack: P&L, cash, AR aging, variance notes.
Template
- Summary: revenue, margin, cash runway, top drivers (4 bullets).
- P&L variance: month vs prior; include brief narratives.
- Cash: inflows/outflows; forecast next 8 weeks.
- AR aging: current, 30/60/90+; actions per account.
Distribution
- Export PDF + a 1-page narrative to stakeholders.
- Store in a folder with month-year naming.
Reference
- For plain-English cash-flow basics, this small-business overview is useful: https://www.sba.gov/article/2020/mar/02/small-business-cash-flow-basics
Comparison Table: Manual vs Autopilot Books
| Area | Manual Pain | Autopilot Fix | KPI |
|---|---|---|---|
| Receipts | Missing proof | OCR + rules + weekly review | % with receipt |
| Invoices | Late sends | Invoice on signature + reminders | DSO |
| Reconciling | Line-by-line | Match rules + reason codes | Hours to close |
| Vendor bills | Duplicates/late fees | Duplicate checks + run calendar | Late fees |
| Reporting | New format each time | Fixed template + narrative | Hours/report |
| Audit | Scramble for docs | Attach receipts + logs | Findings |
Starter Stacks (Copy & Adapt)
“Never Miss a Receipt”
- Mobile OCR app + vendor rules
- Weekly exception review
- KPI: ≥95% receipts attached
“Cash In on Time”
- Contract → invoice automation
- Payment links + 3 reminders
- KPI: DSO down 20–30%
“Close in a Day”
- Bank feed + match rules
- Reco report + reason codes
- KPI: hours to close < 8
“Lean Reporting”
- One-click P&L/cash pack
- 1-page narrative template
- KPI: pack < 60 minutes
Implementation Checklist
- Turn on bank feeds and vendor mapping.
- Lock invoice template (logo, fields, terms).
- Create reminder cadence and test payment links.
- Define matching rules; set approval thresholds.
- Build monthly pack template and schedule the export.
- Back up data; test export (CSV/PDF) quarterly.
30-Day Plan
Week 1: Connect feeds; set up OCR + rules; lock invoice template; baseline DSO & close time.
Week 2: Go live with invoice-on-signature; enable reminders; start vendor inbox.
Week 3: Tune matching rules; attach missing receipts; draft the monthly pack.
Week 4: Publish before/after metrics; formalize approvals; plan quarter-end checklist.
Security & Privacy (Plain English)
- MFA on banking and accounting apps; no shared passwords.
- Roles: separate who creates bills from who approves payments.
- PII redaction: receipts may contain personal info—mask or avoid storing.
- Retention: define how long you keep invoices/receipts; follow local law.
- Export plan: know how to leave your provider with all your data.
Templates You Can Copy
Invoice Reminder (polite)
Subject: Friendly reminder – Invoice [#]
Body: “Hi [Name], invoice [#] for [project] is due on [date]. You can pay securely here: [link]. If already paid, thanks—no action needed.”
Month-End Narrative (1 page)
- Highlights (4 bullets): revenue/margin/cash drivers.
- Variances (3): what changed and why.
- Risks (2): expected impact + mitigation.
- Next steps (2): actions before next pack.
Reconciliation Notes
- “Matched by vendor + memo pattern; tolerance ±€1.00; receipt attached.”
FAQs
Cash or accrual?
Pick one and stay consistent. If you invoice work delivered over time, accrual usually tells a truer story.
What if a client won’t pay on time?
Shorten payment terms, require deposits, and pause new work until caught up.
Do I still need an accountant?
Yes—for taxes and oversight. Automation reduces grunt work; a pro guards your compliance.
How often should I review vendors?
Quarterly. Cancel unused seats; renegotiate annual rates.
Internal Links (add them at the end)
- /entrepreneurs-automation-stack
- /automate-client-onboarding
- /inbox-calendar-automation-founders
- /automate-reporting-dashboards
- /legal-security-automation-small-biz