| Tool | Plan | Monthly Cost | Notes |
|---|---|---|---|
| Dropbox | Professional (3 TB) | $20 | Billed annually. Handles RAW + edited file volume for 32+ jobs/mo comfortably. |
| Google Workspace | Business Starter (you have this) | $7 | Already paying — keep for Sheets job log and Gmail. |
| Claude Pro | Pro | $20 | Required for Cowork. Nightly unbilled job sweep, weekly revenue summary. |
| Calendly | Standard (optional) | $12 | Only needed if HoneyBook scheduler doesn't fit your flow. Try built-in first. |
| Pic-Time or Shootproof | Entry tier (optional) | ~$15–25 | Branded gallery delivery. Nice-to-have, not essential if Dropbox links work. |
| Found.com | Banking only | $0 | Free business banking. Invoicing moves to CRM — Found stays for the bank account. |
Jobber Core is cheaper on paper, but it's built for trades and field service — landscapers, cleaners, plumbers. It lacks native contract/e-signature tools and requires a $119/mo upgrade to get automations. At your volume, automations aren't optional.
HoneyBook Essentials was designed for exactly your type of business — photographers, videographers, creative service providers. Automations, a branded client scheduler, contracts, and invoicing are all included at $49/mo (annual).
If you want Jobber with automations, you'd be paying $119/mo for the Connect plan — making HoneyBook $70/month cheaper for equivalent functionality.
Recommendation: HoneyBook Essentials, billed annually