Timely has four plans. The free trial gives you Pro for 7 days; after that you stay on whatever you've configured (or downgrade to free-tier read-only access).
The tiers
| Starter | Pro | Business | Enterprise | |
|---|---|---|---|---|
| Price (monthly) | $29/mo | $79/mo | $149/mo | Custom |
| Price (annual, per month) | $24/mo | $66/mo | $124/mo | Custom |
| Locations | 1 | 5 | 20 | Unlimited |
| Employees per location | 25 | 75 | 200 | Unlimited |
| Schedule grid | ✓ | ✓ | ✓ | ✓ |
| SMS shift alerts | ✓ | ✓ | ✓ | ✓ |
| Email + PDF publish | ✓ | ✓ | ✓ | ✓ |
| CSV import / export | ✓ | ✓ | ✓ | ✓ |
| Calendar feed (ICS) | ✓ | ✓ | ✓ | ✓ |
| Schedule rules | — | ✓ | ✓ | ✓ |
| Smart Copy | — | ✓ | ✓ | ✓ |
| Conflict detection | — | ✓ | ✓ | ✓ |
| AI Scheduler | — | 4 / month | Unlimited | Unlimited |
| Schedule analytics | — | — | ✓ | ✓ |
| Labor cost dashboard | — | — | ✓ | ✓ |
| Square / Gusto / QBO sync | — | ✓ | ✓ | ✓ |
| SSO / audit logs / API | — | — | — | ✓ |
Annual billing saves ~17%. Switching between monthly and annual is a one-click change in Settings → Billing.
How the trial works
Every new signup gets a 7-day free trial of Pro. You enter a payment method during signup (so we know the trial is from a real customer), but we don't charge anything for 7 days. Three days before the trial ends we send a reminder email.
When the trial ends:
- If your card is good — Stripe charges the Pro monthly rate and you continue on Pro seamlessly.
- If your card declines — the subscription enters
past_due. You see a banner in-app prompting you to fix it. After Stripe's retry window (~7 days), the subscription cancels and the org reverts to free-tier capabilities. - If you cancelled during the trial — at trial end, no charge happens, and you drop to free-tier. Your data is intact and you can re-subscribe any time.
Cancel anytime from Settings → Billing → Manage subscription. We won't ask why, but if you'd tell us at support@trytimely.com we'd appreciate the feedback.
What happens when I downgrade?
Downgrading is non-destructive — your data persists across plan changes:
- Schedule rules that you'd built on Pro still exist after a downgrade to Starter, but they don't fire (the rules engine is gated). Re-upgrade to Pro and they reactivate exactly as you left them.
- Analytics history stays in the database. Downgrade from Business to Pro and the dashboard pages disappear from the nav, but the underlying data is preserved.
- Locations exceeding the new limit — e.g., downgrading from Business (20 locations) to Pro (5) when you have 7 locations — disable but stay listed. Schedules at those locations are read-only until you upgrade or remove some locations.
You can re-upgrade at any time, no data loss.
Free tier (post-trial)
If your trial ends without conversion, you don't lose access entirely — you drop to a free read-only tier:
- Past schedules remain viewable
- Employee + location data is intact
- You can no longer build new schedules, send SMS/email, or use any paid features
- An upgrade banner persists across pages
This is intentional. If you come back six months later, your data is exactly where you left it.
Enterprise
Enterprise is custom — multi-org accounts, dedicated SSO, audit logs, REST API, custom SLAs, volume pricing. Reach out at trytimely.com/contact to start a conversation.