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Small Business Compliance Calendar

Every filing, renewal and licence with the working days of preparation it needs and the one input that has to exist first.

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What you get

Pack of 7 files: 3 documents, 4 spreadsheets

Small Business Compliance Calendar
  • How Lead Time Is SetDocument
  • Obligation NotesDocument
  • Owner AssignmentDocument
  • Obligation RegisterSpreadsheet
  • Deadline CalendarSpreadsheet
  • Renewal TrackerSpreadsheet
  • Penalty ExposureSpreadsheet
RiverSmall Business Compliance Calendar

Obligation Register

[Business] — compliance year [20__]

Lead Time and Blocking Input are required fields. A row without them is a date, and everybody already has the dates.

IDObligationAuthorityApplies becauseDueLead time, working daysBlocking inputInput readyDays availableShortOwner
OB-01——————————
OB-02——————————
OB-03——————————
OB-04——————————

The three fields, and why the third one is the point

Due dateWhat the authority sets, with the weekend rule it actually applies
Lead timeWorking days of preparation, including the part that is chasing other people
Blocking inputThe one thing that must be finished before preparation can start, and the date it is really ready

Due date minus lead time is a start date. Working days between the input and the deadline, minus the lead time, is the shortfall. Everything else in the pack is those two subtractions.

Nobody misses a filing because they did not know the date. They miss it because on the date everybody knew about, the thing the filing is made out of did not exist yet. So this pack gives every obligation two fields a deadline list does not carry: how many working days of preparation it needs, and the one input that has to be finished before that preparation can start.

Halden Mechanical is an invented HVAC company: incorporated in Delaware, three Texas locations, 34 employees, 61 subcontractors. Six of its obligations fell on three dates inside a thirteen-day window, which reads as one busy fortnight. Backed off by their own lead times the same six had to begin across four separate weeks, the earliest on 17 December, in a year the calendar did not cover. A due-date list structurally cannot show that. Five waited on one input, the payroll year closing, which happened on the twelfth working day of January.

Four of the fifteen could not fit their lead time between the input arriving and the deadline, fifty-two working days short between them. The worst needed thirty days and had six, waiting on a signed form back from all 61 subcontractors. That penalty is charged per return and again per payee statement, so 61 people is 122 chargeable failures and $7,320 on the first day of lateness. A notice from the state, an insurance renewal, or a customer's data request landing mid-season is separate work again, tracked in the data privacy and customer data pack.

Every sheet in the pack, filled in for one season

The register with its shortfalls, the same rows in start-date order, the exposure priced on each authority's own basis, and the renewals.

Small Business Compliance Calendar
RiverObligation Register

Obligation Register

Halden Mechanical, 2026 season. Fifteen obligations, eight authorities. Days available counts working days between the blocking input arriving and the deadline.

IDObligationDueLeadBlocking inputReadyAvailableShort
OB-01Form 1099-NEC to 61 subcontractors02 Feb30Signed form with a matching number, all 6123 Jan624
OB-08Workers compensation payroll audit20 Feb25Insurance certificate from all 6106 Feb916
OB-10Contractor licence renewal28 Feb20Continuing education, both licence holders10 Feb128
OB-05Form 300A posted at three establishments01 Feb12Payroll year closed20 Jan84
OB-02Form W-2 to 34 employees02 Feb8Payroll year closed20 Jan90
OB-04Form 940, federal unemployment02 Feb4Payroll year closed20 Jan90
OB-09General liability and auto renewal01 Apr45Payroll year closed20 Jan500
OB-07Delaware annual report and franchise tax01 Mar5Prior year books closed02 Feb180
OB-11Form 1120 or extension15 Apr25Prior year books closed02 Feb510
15 ROWS8 authorities, 6 distinct blocking inputs 197   52

Five obligations wait on the payroll year closing and four on the books closing. Neither group is visible in a due-date list, because every obligation in each group has a different deadline and they are never listed next to each other. Closing payroll on the fifth working day of January rather than the twelfth gives OB-05 fifteen days against a lead time of twelve, and that shortfall disappears without anybody working faster.

RiverDeadline Calendar

Deadline Calendar

The same rows in start-date order, grouped by week. The last column is what this week is for.

WeekStartIDObligationDueShortWhat this week is for
15 Dec17 DecOB-01Form 1099-NEC, 61 subcontractors02 Feb24Start the chase. The only start date in the previous calendar year
12 Jan14 JanOB-05Form 300A, three establishments01 Feb4Review the three logs now, so only the totals wait on payroll
12 Jan14 JanOB-08Workers compensation audit20 Feb16Second chase against the same 61 people, different document
12 Jan15 JanOB-15Sales and use tax, December20 Jan0Routine
19 Jan21 JanOB-02Form W-2, 34 employees02 Feb0Payroll closed yesterday. One day of slack against the start date
26 Jan27 JanOB-04Form 94002 Feb0Routine once payroll is closed
26 Jan27 JanOB-09General liability and auto renewal01 Apr0Ten weeks out, which is what 45 working days means
26 Jan28 JanOB-03Form 941, fourth quarter02 Feb0Routine once payroll is closed
26 Jan30 JanOB-10Contractor licence renewal28 Feb8Cannot start. The class with seats does not run until 10 February
23 Feb23 FebOB-07Delaware annual report01 Mar0Run both calculation methods before filing
23 Feb26 FebOB-06Form 300A electronic submission02 Mar0Austin only. The other two post but do not submit

Due-date view: six obligations on three dates inside thirteen days. One busy fortnight.
Start-date view: the same six begin across four weeks, from 17 December, forty-seven days before the last of those deadlines.

Fifteen obligations, 197 working days of preparation, inside a season containing 94 working days. They have to overlap. The register is what says which ones safely can, and the week of 26 January is where four of them start at once.

RiverPenalty Exposure

Penalty Exposure

Priced on each authority's own basis, because the bases are not comparable and averaging them hides the expensive ones.

IDBasisUnits1 day late31 daysAfter 1 AugWorst case
OB-01Per return, and again per payee statement122$7,320$15,860$41,480$82,960
OB-02Per return, and again per payee statement68$4,080$8,840$23,120$46,240
OB-115% of the tax due per month or part month$47,300$2,365$4,730$11,825Capped at 25%
OB-07Fixed penalty plus 1.5% a month on both$8,400 tax$8,600$8,729$8,987Loss of good standing
OB-05Citation per establishment not posted3Not a figure the business can compute in advanceThree citations
OB-09No penalty. A lapse is an uninsured week1 policy—Breach of every contract requiring cover
OB-10Revenue under contracts requiring the licence2 agreementsNot priced in money by the authority at all$412,000
OB-01 + OB-02Both payroll information return sets190$11,400$24,700$64,600$129,200

The step from day thirty to day thirty-one costs $13,300 and nothing about the work changes on that day. Sorted by money the order is OB-01, OB-02, OB-11, OB-07. Sorted by what would actually damage the business it is OB-10, OB-09, OB-07, OB-01. Neither of those is the due-date order, which is the only order most compliance calendars offer.

RiverRenewal Tracker

Renewal Tracker

Separate from the register on purpose. A filing has a fixed date every year. A renewal runs from an anniversary, so it moves, and the condition attached to it takes longer than the renewal does.

RenewalRuns fromExpiryCondition attachedCondition leadStatus
Contractor licenceLicence anniversary28 FebContinuing education, both named holders20Completed 10 Feb, twelve working days out
General liability and autoPolicy inception01 AprPayroll and revenue estimates45Provided 27 Jan, bound 27 Mar
Workers compensationPolicy inception01 JulPrior year audit closed, needing 61 certificates25Audit held with seven certificates outstanding
Registered agentAppointment anniversary30 JunNone2Not started
Fire and life safety inspectionLast inspection date14 SepRemediation of the prior findings15Two findings open since last year
Vehicle registrationsAnniversary per vehicleRollingCurrent inspection per vehicle3Nine of eleven current

The licence renewal is a form and a fee. The class both holders had to sit is the obligation, the December booking was cancelled, and the next one with seats ran on 10 February. An uninsured subcontractor gets charged to the workers compensation policy as if they were payroll, so seven missing certificates is an adjustment invoice rather than a compliance failure, and it lands as cash in the following month.

Edit with AI

What's in the pack

01

Obligation Register

One row per obligation, grouped by authority, each citing the registration, licence, location or headcount that switched it on for you rather than in general. Whether a jurisdiction belongs on this register at all is a separate question, answered first by entity and foreign-qualification tracking.

02

Deadline Calendar

The same rows in start-date order, grouped by week, with the collisions called out and one sentence per row on what that week is actually for.

03

Renewal Tracker

Renewals run from anniversaries rather than fixed dates, and each carries the condition attached to it, which is the part that takes the time.

04

Penalty Exposure

Every obligation priced on its own authority's basis: per return, percentage of the liability, fixed penalty plus interest, or revenue at risk.

05

How Lead Time Is Set

The four-minute method behind the rest of the pack, including the three-part estimate and the three honest answers to a shortfall.

06

Obligation Notes

Why each obligation applies, what the preparation really consists of, the trap in it, and what changed since last year.

07

Owner Assignment

A name against every row, with the preparer, the chaser and the signer separated, because some signatures cannot be delegated.

08

Lead Time Sweep

A weekly agent that runs against start dates rather than due dates, so the reminder arrives while there is still time to prepare.

How to use it

  1. 1

    Open in River, or download it

    Take the blank Word and CSV files away with no account, or install the pack in River and let the agent build the register from your own paperwork.

  2. 2

    Send what you are registered for

    Formation documents, state registrations, licences, insurance declarations and last year's filings. Your locations and headcounts are enough to begin.

  3. 3

    Put a lead time and a blocking input on every row

    The lead time is estimated in three parts, and the chase part, which is the one nobody counts, is usually the largest of them.

  4. 4

    Read the shortfalls, then move an input

    Where an obligation cannot fit its lead time, the cheapest fix is almost always an input arriving earlier rather than anybody working faster.

Frequently asked questions

Is this template free?

Yes. The four sheets and three documents download as Word and CSV files with no signup and no credit card. "Edit with AI" is the optional path where the agent reads your own registrations and filings and builds the register from them. The other packs sit in the template library.

What format are the downloaded files?

Word documents (.docx) for the three method and notes documents, and CSV (.csv) for the Obligation Register, Deadline Calendar, Renewal Tracker and Penalty Exposure, zipped together. They open natively in Word, Pages, Google Docs, Excel, Numbers and Sheets.

How is this different from a compliance calendar checklist?

Those are lists of dates for businesses in general, and the dates were never the hard part. This one is built from what you are actually registered for, and every row carries the preparation time and the one input that has to exist first, so it sorts on start dates.

Why does location matter so much?

Scope is where generic lists are most wrong. The OSHA annual summary posts at every establishment that owes one, and deciding which ones do runs its own separate size and industry tests, worked through in the workplace safety and posting pack. A company of 34 across three sites can have one establishment in scope for it and two out.

Does it tell me what my deadlines are?

It records what your own filings, notices and licences say, and asks you to confirm anything it cannot source. It is not legal or tax advice. Where something has already lapsed it says so and prices it, which is the point at which a professional is worth paying.

Which penalties does it price?

Whatever the authority publishes. Information returns run per return and are charged twice. Delaware adds a fixed penalty plus 1.5% a month on tax and penalty together. A lapsed licence has no dollar figure at all and is usually the largest exposure you have.

Who is this template for?

Owners with more than one location, more than one authority, or contractors on the payroll file, where nobody's whole job is compliance. It suits a small business workspace. Accounting firms tracking client filings want the client filing calendar instead. A location applying for a licence it does not have yet needs the licence and permit application pack first, not this one.

Sources

  1. IRSInformation return penalties (opens in a new tab)
  2. Occupational Safety and Health Administration1904.32 — Annual summary (opens in a new tab)
  3. Division of Corporations - State of DelawareAnnual Report and Tax Instructions (opens in a new tab)

Written by

Chandler Supple

Co-founder & CEO, River

Chandler has spent the last six years working in AI, building tools for millions of users and Fortune 100 companies. In 2025, he co-founded River to build a new kind of operating system for AI agents.

LinkedInGitHubX

Reviewed by

Brian Joseff, Co-founder, River

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Find out which deadline you have already missed the start of

Download the blank pack as Word and CSV files, or open it in River and have your own registrations, licences and filings read and backed off the due dates first.

Edit with AI