Automate with confidence. This checklist translates legal and security basics into founder-friendly actions: policies, access, data handling, DLP, logs, and vendor checks—so audits don’t derail growth.
Table of Contents
- Who This Guide Is For
- Principles (Secure by Design, Evidence by Default)
- Policies You Actually Need (Short & Useful)
- Access & Identity (Who Can Do What)
- Data Handling & Retention (Keep It Lean)
- DLP & Content Controls (Prevent Oops Moments)
- Logging & Observability (Prove It)
- Vendor Due Diligence (Trust but Verify)
- Comparison Table: Minimum Viable Controls
- Starter Stacks (Copy & Adapt)
- Implementation Checklist
- 30-Day Plan
- Legal & Privacy (Plain English)
- Templates You Can Copy
- FAQs
- Internal Links (add them at the end)
Who This Guide Is For
Entrepreneurs and small teams wiring automation across CRM, billing, docs, and support. You’ll get plain-English policies, controls, evidence to keep, and a 30-day plan to bake safety into day one.
Pair with Bookkeeping on Autopilot for audit-ready receipts/invoices → /automate-bookkeeping-entrepreneurs and Customer Support with AI for permission-aware knowledge → /ai-customer-support-rag.
Principles (Secure by Design, Evidence by Default)
- Identity first: SSO/MFA; no shared passwords; revoke access fast.
- Least privilege: assistants/tools only see what they need.
- Data minimization: store less; mask PII; set retention windows.
- DLP boundaries: block uploads of sensitive data where it doesn’t belong.
- If it’s not logged, it didn’t happen: prompts, outputs, access changes.
Policies You Actually Need (Short & Useful)
- Acceptable Use: what can/can’t be uploaded or pasted into tools (no PII, no financial secrets).
- Privacy Notice: what you collect, why, how long, with whom (and user rights).
- Data Retention: how long you keep invoices, emails, logs; deletion schedule.
- Incident Response (1 page): who to notify, within how long, steps to contain and report.
- Third-Party/Vendor: how you pick tools, list of sub-processors, exit plan.
Where to keep them
- A “Policies” folder; link from your site footer (Privacy/Cookies as required).
- Internal page with last-review dates and owners.
Access & Identity (Who Can Do What)
- Set up MFA everywhere (email, accounting, CRM).
- Use role-based access: viewer vs editor vs admin; avoid “everyone is admin.”
- Contractor access: time-boxed; least privilege; NDA signed; revoke on contract end.
- Quarterly access review: export users/roles; close or downgrade dormant accounts.
Evidence to keep
- User/role inventory, last login, admin actions, access changes log.
Data Handling & Retention (Keep It Lean)
- Map data flows: forms → CRM → email → billing → storage.
- PII minimization: don’t store sensitive IDs in notes; use secure fields or vault.
- Retention windows: e.g., receipts/invoices 5–7 years (local law), marketing leads 12–24 months of inactivity.
- Right to delete/export: know how to honor requests quickly.
Evidence to keep
- Data map, retention policy, proof of deletion/export on request.
DLP & Content Controls (Prevent Oops Moments)
- DLP rules: block uploads of card numbers, IDs, health data in general tools.
- Allow-lists: only approved drives/folders; deny-lists for risky domains.
- Redaction: mask PII in logs, screenshots, and training sets.
- Outbound checks: warn before sending messages externally with sensitive terms.
Evidence to keep
- DLP rules list, blocked-event log, exception approvals.
Logging & Observability (Prove It)
- Prompt/output logging for AI tools with user ID and timestamp.
- Change logs for templates, rules, and automations (who changed what).
- Export to archive monthly (CSV/JSON/PDF) and store in your “Audit” folder.
- Alerting: notify on admin changes, unusual volumes, or failed automations.
Evidence to keep
- Monthly log exports; anomaly summaries; remediation notes.
Vendor Due Diligence (Trust but Verify)
- Security posture: SOC 2/ISO 27001 (if available), data residency/options, encryption.
- Data use: opt-out of training on your data by default.
- Sub-processors: documented and updated; change notifications.
- SLA & support: response times, export/exit path if vendor fails.
- Pricing & lock-in: can you export all data and recreate flows elsewhere?
Evidence to keep
- DPA/SLA copies, sub-processor list, security FAQ, pen-test or audit summaries (if shared).
Comparison Table: Minimum Viable Controls
| Area | Must-Have Today | Nice-to-Have Soon | Owner |
|---|---|---|---|
| Identity | MFA + role-based access | SSO, just-in-time roles | Founder/IT |
| Data | Map + retention | Field-level encryption | Founder |
| DLP | Block PII upload | Contextual DLP by role | Founder/Legal |
| Logging | Prompt/output logs | SIEM or central archive | Ops |
| Vendors | DPA/SLA + export path | Independent pen-tests | Founder/Procurement |
| Policy | AUP + Privacy + Incident | Quarterly tabletop test | Founder/Ops |
Starter Stacks (Copy & Adapt)
“Pilot-Ready Controls”
- MFA everywhere; least-privilege roles
- Training opt-out; 90-day log retention
- DLP rules (block PII uploads)
- Weekly error/alert digest
“RAG with Proof”
- Permission-aware indexing
- Citations on by default
- Confidence threshold → human review
- Re-index schedule + QA sample
“Change & Evidence”
- Runbook for exceptions
- Monthly access review
- Log export + backup
- Golden prompts regression test
Implementation Checklist
- Create Policies folder; draft AUP, Privacy, Retention, Incident, Vendor SOP.
- Turn on MFA and downgrade extra admins.
- Write DLP rules + allow-list folders; redact PII in logs.
- Enable prompt/output logging; schedule monthly export.
- Collect DPA/SLA from key vendors; document data residency and export path.
- Add footer links (Privacy/Cookies) and consent text in forms.
30-Day Plan
Week 1 — Baseline & Gaps: export user/roles; list vendors; map data; note missing policies.
Week 2 — Turn On Controls: MFA, role reviews, DLP basics, logging, consent text.
Week 3 — Prove & Train: run an incident tabletop (30 min); test a data deletion/export; record steps.
Week 4 — Evidence & Review: compile an “Audit Pack” (policies, logs, access review); fix gaps; schedule quarterly checks.
Legal & Privacy (Plain English)
- Consent: clear opt-in for marketing; easy opt-out; store timestamps.
- Cookies: banner where required; link to policy; honor preferences.
- Contracts: e-sign with audit trail; store signed copies centrally.
- Data requests: be able to find, export, or delete a contact in days, not weeks.
- Jurisdictions: if you sell in the EU/UK, pay attention to data transfers and processors; pick vendors with EU data options.
Templates You Can Copy
Acceptable Use (excerpt)
“Do not upload or paste payment card data, national IDs, health data, or client secrets into general tools. Use approved storage only. AI outputs must be reviewed before external sharing.”
Incident Message (internal)
“We detected [issue] at [time]. Impact so far: [systems/data]. Actions taken: [containment]. Next update: [hh:mm]. Owner: [Name].”
Vendor Checklist (short)
- Residency options?
- Data used for training by default?
- Sub-processor list & change notice?
- Export all data? Format?
- SLA for incidents and support?
FAQs
Do I need a lawyer?
For specific jurisdictions and contracts, yes. This checklist keeps you safe day-to-day, but a short legal review pays off.
Is MFA really necessary?
Yes—most breaches start with stolen credentials. MFA blocks the easy path.
How long should I keep logs?
90 days minimum for troubleshooting; 12 months if you can (storage is cheap; privacy rules still apply).
What if a vendor won’t sign a DPA?
Pick another. If you handle customer data, a DPA is non-negotiable.
Internal Links (add them at the end)
- /automate-bookkeeping-entrepreneurs
- /ai-customer-support-rag
- /entrepreneurs-automation-stack
- /automate-lead-capture-nurture
- /inbox-calendar-automation-founders
- /automate-reporting-dashboards