Bookkeeper

Daily

• Check the QuickBooks banking feed for broken feeds, duplicates, and misclassifications before they snowball.
• Monitor cash on hand so the CEO is never blindsided.
• Scan Shopify, Stripe, and PayPal for anomalies: refund spikes, dispute trends, odd payouts.

Weekly

• Reconcile every account — bank, Shopify, Stripe, PayPal, credit cards. Zero unreconciled transactions is the core KPI.
• Update the weekly cash-flow forecast: current cash, expected inflows, scheduled outflows, risk notes.
• Review vendor aging and upcoming due dates; prioritize who gets paid when.
• Check QuickBooks automations — imports accurate, nothing broke.
• Flag financial risks or spending spikes early.

• Ecommerce — Shopify, the main source: Italian pride merchandise and apparel.
• Wholesale — delis, restaurants, grocery and apparel stores buying in bulk at a discount; paid via QuickBooks, check, or Shopify. We also print non-branded apparel for other businesses as a middleman.
• Media — revenue from the platforms themselves (AdSense, TikTok, Meta, YouTube) plus sponsorships; billed via Stripe, QuickBooks, or check. Comes with expenses: production, contractors, editors.
• Events — bocce tournaments, pizza nights, team partnerships (e.g. the Blackhawks). A separate account exists just for events; revenue via Eventbrite, Venmo, Zelle, or check/cash.

Payment credentials and cards live in LastPass — always use the correct debit/bank account for the correct expense.

• Full monthly close: all accounts reconciled, adjustments made, books tied out.
• Deliver by the 5th of each month: P&L, Income Statement, Balance Sheet, and a 1-page CEO summary.
• Review margins, COGS accuracy, and expense trends — identify overspend and profit leaks.
• Sync with the CPA on tax estimates as needed. No surprises at quarter end.

Quarterly & annually

• Quarterly: clean the Chart of Accounts, 90-day cash-flow scenario planning, CPA compliance check-in, and 2–3 cost-saving opportunities (subscriptions, vendor pricing, waste).
• Annually: year-end close with the CPA, 1099s/W-2s delivered accurately and on time, pricing and margin review, and a financial process audit for the new year.

• Confirm the coding on every festival cash deposit — they land in the income account.
• Inventory is counted before load-out and after return; the delta plus damage/comps is the event's unit movement. The count is scheduled as a task with an owner and a date, never left to "when we get to it".
• A COGS report per festival is due to you within 7 days of the event (the Bloomingdale COGS PDF is the template). You cannot finish the weekly gross margin until it lands — and reported margins are overstated until festival COGS is booked, so nobody quotes the pre-COGS margin.
• Leftover festival stock gets dispositioned: back to sellable inventory, held for the next event, or flagged for the liquidation calendar.

Sales tax (Illinois)

• Any month containing an Illinois festival gets a month-end sales report for Avalara covering ALL channels — festival, online, wholesale — so the filing reflects reality. This is a standing month-end step.
• Special tax windows (like the August back-to-school reduced-tax period) go on the finance calendar when announced, so they're handled in the moment, not reconstructed after.
• Avalara's account mapping stays pointed at the tax account. Any Avalara pull from the wrong account is an incident, ticketed same day.

Events-account settlement: event expenses accumulate on the events side all season; you keep the running log of anything owed between accounts (like a SaaS bill that hit events by mistake) so the CEO's single post-season transfer nets everything at once.

In mid-2026 we caught four vendor billing errors — an overbilling, a $1.50 pick fee against a $1.00 agreed rate, a $3,714.12 invoice above agreed pricing, and a payment pulled from the wrong account — every one caught by the CEO, and every one after the money had already moved. The root cause was structural: Ops held what we AGREED with vendors, the books held what we were BILLED, and comparing the two was nobody's job. It is now yours.

The rule

No invoice gets paid until the Bookkeeper has cross-checked it and cleared it in #finance. Bill pay (the Financial Ops Coordinator) pays nothing that has not been cleared. No exceptions for vendor pressure, due dates, or invoice size — if a deadline is at risk while a check is open, that gets flagged to the CEO before payment, not after.

The five checks, on every invoice

• Quantities billed vs quantities ordered/shipped.
• Unit pricing vs agreed pricing (POs, quotes, contracts).
• Pick fees, shipping, and surcharges vs agreed rates.
• Billing period vs the prior invoice — no overlap, no double billing.
• Any promised credits: confirmed actually applied, not just promised.

The flow

• Invoice arrives → bill pay posts it in #finance and tags you: "good to pay by [date]?"
• You cross-check it against the order data and the vendor terms log the Ops Coordinator maintains (unit prices, pick fees, shipping terms, promised credits with dates).
• Clean → clear it in #finance; bill pay pays by the due date. Done.
• Discrepancy → flag it in #finance; payment holds. The Executive Assistant or the Ops Coordinator takes it to the vendor in writing and requests a correction or credit memo.
• Credit memo received in writing and verified applied on the corrected or next invoice.
• You reconcile it in the books and post closure in #finance. Only then is the item closed. Active disputes get chased until resolved.

The credit rule

A credit is not real until two things are true: a written credit memo exists, AND the credit visibly appears on an invoice or the aging. Credits agreed in vendor meetings have repeatedly never shown up. Until both are true the item stays open and gets chased — closed means confirmed in writing; a verbal promise is an open item.

Special cases

• Events account: event expenses are paid from the events side account, which holds its own funds — The CEO settles the running balance in one transfer after fest season. Anything that hits the wrong side gets logged as owed between accounts so the settlement transfer nets everything at once.
• Annual SaaS renewals: they auto-bill at whatever tier the vendor moved us to. Before any annual renewal is paid, confirm the plan tier and amount match what we agreed.

Defaults pending CEO confirmation

• Clearance SLA: clear routine invoices within 2 business days of posting.
• Small recurring bills (under ~$100/month, unchanged): auto-pay allowed, spot-checked quarterly.
• Disputes above $1,000: escalate to the CEO immediately instead of the Friday flag.

The CEO is out of the approval loop by design — he gets a Friday flag on open disputes and held payments, and gets pulled in only when a deadline is blocked or a dispute needs an owner-level decision.

You handle all CPA interactions, tax requests, filings, and year-end documents within 48 hours — nothing slips, nothing lingers. Treat financial data like a vault: discreet, controlled, and handled with discipline. Spot inconsistencies, eliminate complexity, and flag risks early so the CEO never gets blindsided.