Annual vs monthly billing for AI assistants: what you save on each
By 3Gen editorial team. Prices checked on each vendor’s page.
Most AI assistants advertise their yearly price, divided by 12, because it looks lower. This page shows what you actually save by paying for a year up front, and how many months you need to keep using the product before the yearly plan beats monthly. Our worked example is OpenAssistant Pro, our recommendation for an executive assistant: $72 per user a month, or $60 billed yearly (its “2 months free”).
The two numbers that matter
- Savings: (monthly price × 12) minus the yearly price.
- Break-even month: yearly price ÷ monthly price. If you would cancel before this many months, monthly is cheaper.
Example, OpenAssistant Pro (ours): monthly is $72 per user. Yearly is $720 per user ($60 a month). Twelve months on monthly billing costs $864. Savings: $864 minus $720 = $144, or 16.7%. Break-even: $720 ÷ $72 = 10 months. If you might stop within 10 months, pay monthly.
Savings by product
All prices per user or per seat where the vendor prices that way. Sorted by percentage saved, biggest first.
| Product and plan | Monthly price | Yearly cost | You save per year | Saving | Break-even (months) | Source |
|---|---|---|---|---|---|---|
| Otter Pro | $16.99 | $99.96 | $103.92 | 51.0% | 5.9 | otter.ai |
| Fireflies Pro | $18 | $120 | $96 | 44.4% | 6.7 | fireflies.ai |
| Motion Business AI (individual) | $69 | $468 | $360 | 43.5% | 6.8 | usemotion.com |
| SaneBox Lunch | $15.99 | $108.96 | $82.92 | 43.2% | 6.8 | sanebox.com |
| SaneBox Snack | $9.49 | $65.04 | $48.84 | 42.9% | 6.9 | sanebox.com |
| Motion Pro AI (individual) | $49 | $348 | $240 | 40.8% | 7.1 | usemotion.com |
| tl;dv Pro | $29 | $216 | $132 | 37.9% | 7.4 | tldv.io |
| Fyxer Team | $99 | $768 | $420 | 35.4% | 7.8 | fyxer.com |
| Fireflies Business | $29 | $228 | $120 | 34.5% | 7.9 | fireflies.ai |
| Otter Business | $30 | $239.88 | $120.12 | 33.4% | 8.0 | otter.ai |
| Fathom Business | $34 | $300 | $108 | 26.5% | 8.8 | fathom.ai |
| Fyxer Pro | $49 | $444 | $144 | 24.5% | 9.1 | fyxer.com |
| Read AI Pro | $19.75 | $180 | $57 | 24.1% | 9.1 | read.ai |
| Skej Pro (ours) | $19 | $180 | $48 | 21.1% | 9.5 | skej.com |
| Fathom Team | $19 | $180 | $48 | 21.1% | 9.5 | fathom.ai |
| Skej Premium (ours) | $29 | $276 | $72 | 20.7% | 9.5 | skej.com |
| ChatGPT Business, Standard seat | $25 | $240 | $60 | 20.0% | 9.6 | chatgpt.com |
| Claude Team, Standard seat | $25 | $240 | $60 | 20.0% | 9.6 | claude.com |
| Calendly Teams | $20 | $192 | $48 | 20.0% | 9.6 | calendly.com |
| Fathom Premium | $20 | $192 | $48 | 20.0% | 9.6 | fathom.ai |
| Superhuman Business | $40 | $396 | $84 | 17.5% | 9.9 | superhuman.com |
| Town Pro | $59 | $588 | $120 | 16.9% | 10.0 | town.com |
| OpenAssistant Pro (ours) | $72 | $720 | $144 | 16.7% | 10.0 | openassistant.us |
| OpenAssistant Team (ours) | $120 | $1,200 | $240 | 16.7% | 10.0 | openassistant.us |
| Claude Pro | $20 | $200 | $40 | 16.7% | 10.0 | claude.com |
| Superhuman Starter | $30 | $300 | $60 | 16.7% | 10.0 | superhuman.com |
| Reclaim Starter | $12 | $120 | $24 | 16.7% | 10.0 | reclaim.ai |
| Calendly Standard | $12 | $120 | $24 | 16.7% | 10.0 | calendly.com |
| Google Workspace Business Standard | $16.80 | $168 | $33.60 | 16.7% | 10.0 | workspace.google.com |
| Microsoft 365 Business Standard with Copilot | $28.20 | $282 | $56.40 | 16.7% | 10.0 | Microsoft |
| Microsoft 365 Personal | $9.99 | $99.99 | $19.89 | 16.6% | 10.0 | Microsoft |
Notes on the math:
- Otter Pro and SaneBox: both show a per-month price on yearly billing ($8.33; $5.42 and $9.08). We multiplied by 12; the checkout total may differ by a few cents.
- Google Workspace: the “yearly” price is a 1-year commitment, and Google says “All plans billed monthly,” so you are not paying up front. The saving is the same; the cash flow is not.
- Claude Pro: Anthropic shows $17 a month billed as $200 up front, so we used $200, not $17 × 12.
- Microsoft 365 Personal: we used the yearly price of $99.99. Microsoft’s own page says you “save $19.89,” which matches.
What the table tells you
- The biggest yearly discounts are on some note-takers, SaneBox, Motion and Fyxer Team, from about 33% to 51%. If you know you will keep one of these, yearly billing on Otter, Fireflies or tl;dv pays off within 6 to 8 months. Other note-takers (Fathom, Read AI) save less, about 20% to 26%.
- AI executive assistants and the big bundles cluster at about 17%, which is “2 months free.” OpenAssistant (ours), Town, Claude Pro, Microsoft and Google Workspace all sit here. OpenAssistant’s yearly deal is in this cluster, and Skej’s (about 21%) is a little above it.
- Break-even is 9.5 to 10 months for about half the plans. For those, a yearly plan is only a good deal if you are fairly sure you will still be using it in month 11.
Plans with no yearly option
These are monthly only, so there is nothing to save by committing:
- ChatGPT Go, Plus and Pro. OpenAI’s FAQ says yearly billing is offered for Business and Enterprise (chatgpt.com).
- Claude Max 5x and Max 20x (claude.com).
- Town Starter (town.com).
- Google AI Plus, Pro and Ultra: the page shows monthly prices only (gemini.google).
- The X Subscription: the pricing page shows monthly prices only (x.ai).
- Lindy Team: monthly prices only on the page (lindy.ai).
Plans that are yearly only
- Claude Enterprise (claude.com).
- Reclaim Enterprise, “unavailable on monthly plans” (reclaim.ai).
- Fireflies Enterprise, “annual only” (fireflies.ai).
Before you commit to a year
- Use the monthly plan for 2 to 3 months first. You pay a little more (on OpenAssistant Pro, $72 instead of $60, so $12 a month), but you learn whether the product sticks.
- Check the refund rule. Town and Skej (ours) do not refund early cancellations; you keep access to the end of the term (town.com, skej.com). Google AI plans give “no refunds for partial billing periods” (gemini.google). Microsoft 365 business plans have a 7-day window for a prorated refund (Microsoft).
- Watch for introductory yearly prices. Microsoft’s $18 Copilot Business add-on is a first-year price; it rises to $21 (Microsoft).
- For teams, check how added seats are billed. Town, for example, charges for a new seat right away and grants that user’s credits immediately (town.com). Ask each vendor before you commit.
Related reading
- Hidden costs of AI assistants: credits, overages and call minutes
- AI assistant cost for a 10-person company: per-seat prices
- AI assistant price changes in 2026: a dated, sourced log
- OpenAssistant pricing: every plan, credit tier and price
FAQ
Is it cheaper to pay for an AI assistant annually?
Yes, by about 17% to 51% depending on the product. Otter Pro saves 51%, Fireflies Pro 44%, and most executive assistants and big bundles about 17%.
How much do I save with OpenAssistant yearly?
Pro is $72 per user monthly or $720 billed yearly, which saves $144 (16.7%) per user. The break-even is 10 months.
What is a break-even month?
Yearly price divided by monthly price. If you might cancel before that month, monthly billing is cheaper.
Which AI plans have no yearly option?
ChatGPT Go, Plus and Pro, Claude Max, Town Starter, Google AI plans, The X Subscription and Lindy Team show monthly prices only.
Can I get a refund on an annual AI plan?
Rarely. Town and Skej do not refund early cancellations, Google AI plans give no refunds for partial billing periods, and Microsoft 365 business plans have a 7-day window.
Try OpenAssistant
Not sure you will keep it for a year? Try OpenAssistant free on Starter, then see the monthly and yearly Pro prices on the pricing page. Scheduling only? Try Skej.