
How to Categorize Calendly in QuickBooks (and Xero)
Calendly posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Per-seat billing prorates mid-cycle. Annual prepays deduct in full under the 12-month rule.
SDO CPA LLC
18 years of experience
Bobby Huang is a partner at SDO CPA. 18 years of hands-on bookkeeping. He still reconciles real client books and built Growthy from the same review-and-approve work bookkeepers do each week.

Calendly posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Per-seat billing prorates mid-cycle. Annual prepays deduct in full under the 12-month rule.

Figma posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Per-editor billing means a free viewer who edits can jump your bill mid-cycle. Annual prepays deduct under the 12-month rule.

Zoom posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Zoom Phone is telecom, not software; Zoom Rooms hardware capitalizes separately. Annual prepays deduct under the 12-month rule.

Slack posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Fair Billing credits are a contra-expense, not income. Annual prepays deduct in full under the 12-month rule.

Salesforce posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Annual prepay is usually deductible in full under the 12-month rule, not auto-capitalized. Multi-cloud bundles split by product.

Notion posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Per-seat billing charges only paid members; Notion AI stays an add-on. Annual prepays deduct under the 12-month rule.

Mailchimp sits in Software/Dues & Subscriptions or Advertising, Schedule C Line 27a or Line 8. No 1099 (Intuit is a corporate payee). Pick a bucket and keep it consistent.

HubSpot posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. The real call is Software vs. Advertising for Marketing Hub. Annual prepays deduct in full under the 12-month rule.

GitHub posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Copilot rides the base line; metered Actions/Codespaces can shift to Cloud Services. Annual prepays deduct under the 12-month rule.

Dropbox posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Dropbox Sign bills separately but stays Software. Annual prepays deduct in full under the 12-month rule.

Docusign posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099. Envelope overages are still Software, just variable. Annual prepays deduct under the 12-month rule.

Canva's subscription posts to Software or Dues & Subscriptions, Schedule C Line 27a. No 1099 (foreign payee, W-8BEN-E). Canva Print is a tangible good, split separately. Annual prepays deduct under the 12-month rule.
See Growthy on a sample book. Read-only bank access.
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