The Founder's Monthly Legal Compliance Calendar

This guide is a practical, jurisdiction-agnostic checklist founders can run every month to stay legally tidy. Use it to set up recurring tasks in your favorite project management tool (like Notion, Asana, or Jira) and attach evidence as you go. It’s not a substitute for legal advice; always confirm specifics with your counsel and local regulators.

This simple rhythm can save you from future headaches, keep your company attractive for investment, and make due diligence a breeze.

Who Should Use This Guide?​

This monthly checklist is designed for organizations that are growing but might not have a dedicated in-house legal department yet. It's particularly useful for:

• Early-stage startups navigating the complexities of governance, employment, and tax without a full-time legal team.
• VC-backed companies that want to maintain clean, organized diligence folders to be ready for the next funding round or acquisition.
• Small and medium-sized businesses (SMBs) that sell products or services across different states or countries and need to manage multi-jurisdictional compliance.

At-a-Glance Monthly Checklist ✅​

Copy these items into your task management tool and set them to recur monthly.

Corporate & Governance​

• Review any changes to the capitalization table; update the option ledger and queue any necessary board consents.
• Sweep the inboxes for your registered agent and your general legal email (e.g., "legal@yourcompany.com"); triage any notices or service of process documents immediately.
• Maintain a running register of resolutions and actions to prepare for the next board meeting.

Tax & Payroll​

• Run payroll on schedule; remit all employee withholdings and employer taxes according to your assigned deposit schedule.
• Reconcile invoices for employee benefits; remit payments for health, life, disability, commuter benefits, etc.
• File sales, VAT, or GST returns and remit collected taxes if you are on a monthly filing schedule.
• Review your physical or economic nexus exposure by tracking headcount, contractor locations, revenue sources, and inventory placement.
• Tag any costs eligible for R&D tax credits and maintain the necessary workpapers to support them.

Employment & Benefits​

• Reconcile your headcount roster against your HRIS (Human Resource Information System); confirm that all new-hire and termination paperwork is complete.
• Deposit employee retirement plan contributions (e.g., 401(k)) and any loan repayments in a timely manner.
• Reconcile paid time off (PTO) balances and ensure overtime compliance for all non-exempt employees.
• Track compliance training completion rates (e.g., harassment, security) and schedule make-up sessions for those who are behind.
• Check that all equity grant paperwork is fully executed and chase any outstanding signatures.

Privacy, Security & Data​

• Perform access reviews for critical systems, including finance software, production environments, source code repositories, customer data stores, and HRIS.
• Update Data Protection Impact Assessment (DPIA) or Records of Processing Activities (ROPA) registers if the product or data flows have changed.
• Log and close out any security or privacy incidents; review the status of Data Subject Requests (DSRs) or other consumer-rights requests.
• Confirm Data Processing Agreements (DPAs) are in place and sub-processor lists are updated for any new vendors.
• Snapshot evidence that backups are succeeding and that restore tests have been performed; summarize the patch status of critical systems.

Finance Controls (Audit-Friendly Close)​

• Reconcile all bank and credit card accounts; formally lock the prior month's books.
• Age your accounts receivable (AR) and accounts payable (AP), actively chase collections, and review top vendor relationships and any unusual spending.
• Apply your revenue recognition policy; tie your monthly recurring revenue (MRR) or annual recurring revenue (ARR) back to customer contracts.
• Document any related-party transactions and ensure they have the proper approvals.
• Refresh your 6–12 month financial runway forecast and check any debt covenants you may have.

Product, Marketing & Website​

• Review recent marketing claims to ensure they are properly substantiated and include any required disclosures.
• Check that your Terms of Service, Privacy Policy, cookie banner, and consent logs are up-to-date after any website or product changes.
• Run open-source license scans on your codebase and update any third-party notices as needed.
• Perform accessibility spot checks on recent product releases to ensure compliance with standards like WCAG.

Licenses, Permits & Industry Rules​

• Verify that all business licenses are current and make note of any pending renewal deadlines.
• Check for any tasks related to sector-specific requirements (e.g., PCI for payments, HIPAA for health data, COPPA for children's privacy, MiCA for crypto-assets, or SOC attestations for enterprise customers).
• Confirm that any changes to money movement or marketplace payment flows do not trigger new licensing requirements.

IP & Brand​

• Monitor trademark watch notices and capture any potential conflicts or infringement issues.
• Confirm that all new employees and contractors have signed invention assignment agreements.
• Review domain name auto-renewal settings and check your DNS security posture.

Insurance & Risk​

• Reconcile the certificates of insurance (COIs) you have issued to customers or partners.
• Review your internal claims and incident log; notify your insurance carriers if required by your policies.
• Adjust your insurance coverage as needed to account for changes in headcount, revenue, or new contractual minimums.

Investor & Board​

• Send your monthly update to investors, including KPIs, cash position, highlights, risks, hiring progress, and any specific asks.
• Maintain the board data room with the latest metrics pack, key new contracts, and compliance documentation.

Records & Retention​

• File all signed contracts, approvals, logs, and other compliance evidence into the correct, organized folders.
• Apply your document retention schedule; properly place or clear any legal holds on documents.

A Simple Monthly Cadence That Works 🗓️​

Spreading the work across the month prevents a last-minute scramble.

• Week 1 – Close & Cash: Focus on closing the prior month's books, reconciling all accounts, and refreshing your runway analysis. This is also the time to run payroll, handle benefits remittances, and deposit retirement contributions.
• Week 2 – Filings & Payments: Submit any monthly sales/VAT/GST returns. Send employer tax deposits according to your schedule. Run your AR collections process and review major vendor payments.
• Week 3 – Controls & Security: This week is for internal checks. Conduct your access reviews, vet new vendors, update DPA lists, review incident logs, and confirm your backup and restore tests were successful.
• Week 4 – Governance & Comms: Compile the board packet and draft your monthly investor update. Sweep legal inboxes for any new items, queue up consents and resolutions for approval, and review your license calendar to prepare for the upcoming month.

Role-Based Ownership (RACI Hint)​

Clear ownership is key. Here’s a typical breakdown:

• CEO/Founder: Responsible for the investor update, board preparation, signing major contracts, and handling policy exceptions.
• Finance/Controller: Owns the financial close, taxes, regulatory filings, AP/AR management, runway forecasting, and archiving financial evidence.
• People Ops: Manages payroll, benefits administration, compliance training, headcount reconciliation, and routing equity paperwork.
• Legal/Outside Counsel: Handles corporate governance, contract review, IP management, licensing, and any active disputes.
• Security/Eng: Conducts technical access reviews, leads incident response, performs vendor security assessments, and runs open-source software scans.
• Ops/IT: Manages device inventory, oversees data backups, and maintains standard operating procedures (SOPs).

Evidence to Capture Each Month (What Auditors and Acquirers Ask For) 📂​

Your future self will thank you for keeping these records tidy:

• Bank reconciliations, trial balance, and the month-end close checklist.
• The payroll register and confirmations of tax and benefit remittances.
• Copies of filed sales/VAT returns and their payment receipts.
• Screenshots or exports from access reviews and notes on any remediation actions taken.
• Logs for DSRs and security incidents, with evidence of their closure.
• Fully executed contracts, board consents, and updated option ledgers.
• Training completion reports and signed employee policy acknowledgements.
• Copies of issued COIs, any claim notices, and communications with insurance brokers.

Jurisdiction Notes (Pattern, Not Advice)​

Compliance details vary by location, but some patterns are common:

• Payroll Taxes: Your deposit schedule (e.g., monthly or semi-weekly in the U.S.) typically depends on your historical tax liability. Your payroll provider will inform you of the required frequency, but you should still confirm the deposits each month.
• Sales/VAT/GST: Filing frequency is often based on sales volume. New sellers might start with monthly filings and can later shift to quarterly or annual as their business changes. Keep a simple register of each jurisdiction’s portal, tax ID, filing frequency, and due dates.
• Retirement Plans: Employee contributions must be deposited as soon as administratively feasible after the payroll date. Do not hold onto these funds.
• Data & Privacy: If you release new product features that change how you collect or process personal data, you must update your records of processing (ROPA) and public disclosures (like your Privacy Policy) in the same month.
• Equity: Employees who make special tax elections (like an 83(b) election in the U.S.) often have very strict deadlines (e.g., 30 days from the grant date). Run a monthly sweep to ensure all recent grantees have been reminded of these deadlines.

Common Pitfalls (and Quick Fixes) ⚠️​

• Auto-Renew Traps: Forgetting to cancel a major contract in time.
  • Fix: Track renewal and termination notice windows for all key vendors. Set calendar reminders 45–60 days before the notice deadline.
• Unowned Portals: The only person with the login to a government tax portal leaves the company.
  • Fix: Centralize all regulator portal logins and multi-factor authentication (MFA) devices/apps in a secure, shared system (like a business password manager). Avoid single-person dependencies.
• Shadow Tools: A team starts using a new SaaS tool without security or legal review.
  • Fix: Implement a simple vendor intake process that requires a review for any new tool that will touch customer or employee data.
• Loose Evidence: Saving compliance proof in random folders or personal drives.
  • Fix: Store evidence (PDFs, screenshots, exports) directly in the associated task in your project management tool and in a clearly named, dated folder structure (e.g., Compliance/2025/2025-08/).
• Access Creep: Former employees or contractors still having access to systems.
  • Fix: Enforce the principle of least privilege. As part of your monthly access review, make it a habit to deprovision all dormant accounts immediately.

Template: Monthly Compliance Checklist (CSV)​

Copy the text below into a text file, save it as compliance.csv, and import it into your favorite spreadsheet or project management tool to get started.

Code snippet

Area,Task,Trigger,Relative Due,Owner,Evidence,Notes
Corporate,Review cap table & option ledger,Month start,Business Day 3,Legal/Finance,Updated ledger export,"Queue any consents"
Corporate,Sweep legal@ and registered agent mail,Month start,Business Day 2,Legal,PDF scans of notices,"Triage/assign"
Tax & Payroll,Run payroll & remit withholdings,Each payroll,Within 2 business days,People Ops/Finance,Payroll register & remittance receipts,"Match pay period"
Tax & Payroll,Deposit employer payroll taxes,Assigned cadence,Per assigned due date,Finance,Deposit confirmations,"Provider portal export"
Tax & Payroll,Sales/VAT/GST return & payment,Monthly filer,Per jurisdiction,Finance,Filed return & payment receipt,"Maintain jurisdiction register"
Tax & Payroll,Review nexus/PE exposure,Month end,Business Day 5,Finance/Legal,Updated nexus matrix,"Headcount/contractor map"
Tax & Payroll,Tag R&D-eligible costs,Month end,Business Day 5,Finance,Workpaper snapshot,"Cost classification notes"
Employment,Reconcile headcount vs HRIS,Month start,Business Day 3,People Ops,Headcount report,"New hire/term packets complete"
Employment,Deposit retirement plan contributions,Each payroll,Within plan timeframe,People Ops/Finance,Deposit confirmations,"Avoid late deposits"
Employment,Reconcile benefits invoices,Monthly invoice,Business Day 7,People Ops/Finance,Invoice & payment,"Credits/refunds tracked"
Employment,Training completion sweep,Month end,Business Day 7,People Ops,Training report,"Schedule make-ups"
Equity,Collect executed grant paperwork,When grants issued,Within 30 days,People Ops/Legal,Executed docs,"Track any tax elections"
Security,Access reviews (prod/code/data/finance),Month start,Business Day 10,Security/Eng,Access exports & remediation log,"Deprovision dormant"
Security,Vendor/DPA review for new tools,New vendors,Within 10 days,Legal/Security,DPA & risk notes,"Sub-processor list updated"
Privacy,DSR/consumer requests log review,Ongoing,Monthly summary,Legal/Privacy,DSR log,"SLA compliance"
Privacy,Update ROPA/DPIA if changed,When features change,Month end,Privacy/Product,Updated registers,"Link to PRDs"
IT/Backups,Backup & restore test snapshot,Monthly,Business Day 10,IT,Test report,"Include RTO/RPO notes"
Finance,Close books & reconcile accounts,Prior month,Business Day 5,Finance,Close checklist & TB,"Lock period"
Finance,AR collections run,Month start,Business Day 7,Finance,Collections notes,"Top delinquent list"
Finance,AP/vendor review & approvals,Week 2,Weekly cadence,Finance,AP aging & approvals,"Spot unusual vendors"
Finance,Revenue recognition & MRR/ARR tie,Month end,Business Day 6,Finance,Rev rec memo & ties,"Contract list"
Licenses,License/permit calendar sweep,Month start,Business Day 5,Legal/Ops,Calendar export,"Upcoming renewals"
IP,Trademark watch & domain review,Month end,Business Day 7,Legal/IT,Watch notices & DNS snapshot,"Auto-renew check"
Insurance,COI issuance & claims log,Month end,Business Day 7,Ops/Finance,COIs & claims notes,"Notify carriers if needed"
Board/Investors,Monthly update to investors,Month end,Business Day 5,CEO/Founder,Update email/PDF,"KPIs, cash, hiring, asks"
Records,Archive evidence to data room,As tasks close,Same day,All owners,Dated PDFs/exports,"Use YYYY-MM folders"

How to Implement in 30 Minutes 🚀​

1. Create a "Monthly Compliance" project in your task manager using the sections above.
2. Add recurring tasks with clear owners and relative due dates (e.g., "3rd business day of the month").
3. As you complete tasks, attach the evidence directly and also save it to a dated cloud storage folder.
4. Create a simple "Jurisdiction Register" spreadsheet listing each state/country where you operate, along with account IDs, portal links, filing frequencies, and due dates.
5. Schedule a one-time meeting with your accountant and legal counsel to review the calendar and adjust any frequencies based on your specific situation.

When Your Company Changes, Update the Calendar​

A compliance calendar is a living document. Revisit and update it when your business hits key milestones:

• Growth: Launching new product lines, expanding to new geographies, or changing how you handle money flows.
• People: Significant headcount growth, hiring contractors in new regions, or shifting your employment model.
• Finance & Ops: Taking on debt with covenants, undergoing SOC or ISO attestations, or signing large enterprise customers with specific compliance requirements.
• Corporate: Making changes to your equity plan, conducting a secondary transaction, or refreshing your option pool.

Bottom line: A steady monthly rhythm transforms compliance from a chaotic fire drill into a predictable, manageable process. This discipline preserves your company's optionality for future fundraising and M&A, and it makes year-end audits and reporting painless. Keep the list short, the evidence tidy, and the owners clear.