Client document chasing for bookkeepers

The idea

Every month-end, the bookkeeper’s real job stops while they beg clients for bank statements and receipts. The chasing is manual, repetitive, and awkward: the same email to the same restaurant owner about the same missing Amex statement, three times, every month. Books close late, which cascades into late VAT or sales-tax filings and annoyed clients who caused the delay themselves.

Keeper and Content Snare prove the pain is real and monetisable, but both price and design for multi-seat firms. The wedge is the 1 to 3 person shop: recurring monthly request lists, a portal so simple that a 60-year-old builder can use it from his phone with no password, and reminders that escalate on their own until every item is ticked. The bookkeeper’s leverage is that the software is willing to nag when they are not.

Who pays

The bookkeeper pays 39 USD/month. A solo practitioner billing 500 to 2,000 USD per client per month across 10 to 30 clients loses billable hours to chasing every single cycle; 39 USD buys those hours back and makes them look organised to clients. Distribution: bookkeeping is intensely community-driven, so target the Bookkeeping Side Hustle and QB ProAdvisor Facebook groups, r/Bookkeeping, and bookkeeper podcasts, where tool recommendations spread fast.

MVP scope

• Recurring monthly request templates auto-instantiated per client
• No-login signed-URL upload portal, mobile-first
• Escalating Postmark reminder ladder that stops on completion
• Accept/reject review flow with rejection reasons re-opening items
• Dashboard ranking clients by oldest missing item
• Skip for v1: QuickBooks/Xero integration, e-signatures, client questionnaires, team seats, white-labelling

Build ChaseList, a web app for solo bookkeepers who need client documents every month. Stack: Next.js (App Router), Supabase (Postgres, Auth, Storage, RLS), Postmark for transactional email. Magic-link auth for bookkeepers.

Data model: Clients have RequestTemplates (recurring monthly item lists, e.g. "Chase business statement, Amex statement, payroll summary, receipts over 500"). On the 1st of each month a cron route instantiates each template into a RequestList with per-item status: pending, uploaded, accepted, rejected (with reason).

Client portal, the key design constraint: no login. Each RequestList gets a signed, unguessable URL emailed to the client. The portal shows their outstanding items as a checklist; they drag files onto an item (stored in Supabase Storage) or mark it not applicable with a note. Mobile-friendly, since clients photograph receipts.

Escalating reminders via Postmark: day 3 gentle nudge, day 7 firmer, day 12 firm with the bookkeeper CC'd, then every 5 days. Reminders list only the still-missing items and stop automatically the moment the list completes. Bookkeeper can pause or manually fire a reminder.

Bookkeeper pages: dashboard (clients ranked by oldest missing item), client detail with template editor, document review with accept/reject, settings/billing.

Pricing: 39 USD/month for up to 30 clients via Stripe; 14-day trial.