Best AI scheduling assistants you cc on email, ranked

Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing.

Short answer: OpenAssistant is an assistant we recommend among assistants you cc. It lets you approve messages before they go out, takes plain-language rules and contact priorities, handles groups across time zones, works by email, text and Slack, and has Coordinator Mode for executive assistants. Blockit is the pick if you want a free plan with a flat meeting count, Howie if you want iMessage, and Clara if you need Exchange.

How these assistants work

You write the email as normal and add the assistant on cc: “Copying Lexy to find us a time.” The assistant then:

1. Reads the thread and your calendar.
2. Replies to the other person with a few times.
3. Handles the back-and-forth (“Tuesday doesn’t work, how about Thursday?”).
4. Follows up if they go quiet.
5. Sends the calendar invite.

The other person doesn’t install anything or click a link. That’s the main reason to use one.

Five questions to ask before you pick one

1. Whose address does it send from? A vendor address (like bot@blockit.com) or one at your own domain? Your own domain usually costs extra.
2. Does it act alone, or ask you first? Some send on their own. Others hold every message for approval.
3. Are you kept on the thread? CC (visible), BCC (hidden), or dropped after the first reply.
4. Can it handle groups? Some are one-on-one only.
5. What does it do with your email? Look for a clear no-training statement and whether humans can read your threads.

Quick picks

Our ranking

This order is an editorial judgment from what each vendor’s pages state about price, calendars, channels, group handling, controls and privacy, considered qualitatively for this use case. Each entry ends with a “pick it if” line, because the best choice depends on your calendar and budget. OpenAssistant ranks first because it pairs documented controls (autonomy per action, contact priorities, CC or BCC) with multiple documented channels and group handling. Blockit comes second for its free tier and similar controls.

1. OpenAssistant (our product)

• Address. The assistant has its own email address and phone number. Pro and up can send from your own domain (OpenAssistant scheduling, OpenAssistant pricing).
• Control.
  • Autonomy is set per action: Manual, Confirmation Window or Autonomous.
  • You choose whether you stay on threads, by CC or BCC (OpenAssistant autonomy help).
  • Blockit offers similar per-person and per-meeting-type autonomy.
• Groups. OpenAssistant says it handles group meetings across time zones (OpenAssistant scheduling). It also takes plain-language rules and contact priorities.
• Price. Pro is $60 per user per month on annual billing or $72 monthly, with credits (OpenAssistant pricing; per-user pricing confirmed by 3Gen).
• Privacy. SOC 2 Type II, and AI providers are contractually barred from training on your data (OpenAssistant trust).
• Where it works. Email, text, Slack or in the app (OpenAssistant pricing FAQ). Its homepage says it makes and receives phone calls (OpenAssistant).
• Coordinator Mode. An executive assistant or coordinator can schedule for a principal using the principal’s calendar and preferences (Coordinator Mode).
• Free credits. Starter is free with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month (OpenAssistant pricing).

Where others do better:

• Price for scheduling alone. Pro costs four times Skej Pro per user ($60 vs $15 on annual billing), and group coordination can use “hundreds” of credits per meeting.
• Free meeting count. Blockit’s free plan gives a flat 15 meetings a month, which is easier to plan around than a credit pool.

Why it’s still our recommendation: it is the only assistant here that documents approve-before-send control, contact priorities, group handling, text and Slack, and an executive-assistant mode together.

Pick it if: you want approve-before-send control, contact priorities and one assistant for scheduling plus inbox and research.

2. Blockit

• Address. It sends as “bot@blockit.com.” A custom domain is Enterprise only (Blockit, Blockit pricing).
• Control. You “Choose your autonomy level,” from reviewing everything to full autopilot, per person or meeting type.
• Groups. Yes. When other attendees also use Blockit, “the meeting autoblocks instantly.”
• Calendars and channels. Google or Outlook, and Slack.
• Price.
  • Free: 15 meetings a month.
  • Lite: 40 meetings, $83 a month on annual billing or $145 monthly.
  • Infinity: unlimited meetings, $395 or $495.
  • 30-day trial on every plan.
• Privacy.
  • SOC 2 Type II.
  • Third-party AI providers can’t train on your data, but Blockit’s privacy notice says it may use your scheduling messages to “improve, fine-tune” its own AI features. A written no-training guarantee is Enterprise only (Blockit privacy, Blockit pricing).
  • Its privacy notice allows human review “for quality assurance purposes if we are alerted of a system error.”

Pick it if: you want a free tier, or an approve-before-send mode.

3. Howie

• How it works. You loop Howie in by email, iMessage or SMS (Howie). It sends as a named assistant. An email at your own domain costs $20 a month extra.
• Groups. The homepage claims it “Finds times across messy group threads.” Howie’s how-it-works document, parts of which are clearly out of date, calls group scheduling “pretty limited” (Howie docs).
• Calendars. The only calendar logo on its homepage is Google’s, and its doc says “only works with Google Calendar.”
• Rules. You can update standing preferences by emailing or texting it, per its doc.
• Price. From $25 a month for 1,250 shared credits, with unlimited teammates (Howie pricing). The cost per meeting isn’t published.
• Privacy. SOC 2 Type II per its homepage and trust center (Howie Trust Center). Howie’s pages state no training policy.

Pick it if: you’re on Google and want to text or iMessage your assistant, or a team wants to share one credit pool.

4. Skej (our product)

• Address. The assistant sends from a skej.com address, such as lexy@skej.com. Premium adds a custom assistant at your own domain (Skej, Skej plans help).
• Control.
  • It acts on its own within your settings. If a contact starts the thread, it asks you first (Skej boundaries).
  • It CCs you on every message by default. Premium’s Unsupervised mode BCCs you on the first reply, then leaves you off (Skej unsupervised mode).
• Groups. Yes, and it books instantly among teammates who use Skej.
• Calendars and channels. Google and Outlook. On paid plans you can also text it or WhatsApp it to manage your own calendar.
• Price.
  • Pro: $15 per user per month on annual billing, $19 monthly.
  • Premium: $23 or $29.
  • The Free plan has no assistant (Skej pricing).
• Privacy. SOC 2 Type II, and “We never train on your data” (Skej trust). Its marketing says no employees read your email, but its AI policy allows “authorized personnel” access for support and troubleshooting (Skej AI and data policy).

Where others do better:

• No approval step. Blockit and OpenAssistant can hold messages for your OK before sending.
• No free assistant. Blockit’s free plan includes its email agent for 15 meetings a month; Skej’s Free plan has no assistant.
• Exchange isn’t listed. Clara lists Exchange.
• No rules by email. Unlike Howie, it won’t save standing rules from an email; you change them in settings.
• Time zones need a heads-up. Its own guide says to tell it when people are in other time zones (Skej quick start).
• No prioritizing. It doesn’t prioritize contacts or bump meetings (Skej boundaries).

Pick it if: you want a low per-user price, both Google and Outlook, and group threads.

5. Clara

• How it works. “Stop scheduling. Just CC Clara.” (Clara).
• Groups. Yes, including multi-time-zone calls.
• Calendars. Google Workspace, Microsoft Outlook and Exchange.
• Preferences. Scheduling windows, buffers, meeting types and priority contacts.
• Price. Standard is $80 a month for 30 meetings. A 14-day free trial covers 5 meetings (Clara pricing). A custom domain is Enterprise only.
• Privacy. Clara says “We never train our models on your data.” Its marketing says “No human at Clara ever reads your emails,” but its privacy policy says engineers “may review emails and other content shared with the Clara assistant for the purposes of debugging technical issues and quality assurance” (Clara privacy).

Pick it if: you’re on Exchange, or you want priority contacts.

6. Calendly Callie

• How it works. You add callie@calendly.com in To or CC. It “does not work in the BCC field,” and you must send from your Calendly login email (Callie how-to).
• Control. Within your rules it sends times and books on its own. It asks you before making an exception to your rules or changing a confirmed meeting (Calendly AI assistant). It tells invitees it’s an AI assistant.
• Groups. No: “Right now, Callie works for one-on-one meetings only” (Calendly AI assistant).
• Speed and availability shown. Calendly says it replies “within 1 minute” and offers up to 3 days of availability with up to 5 slots per day.
• Price. Standard Plus at $18 per seat per month on annual billing, or $24 monthly. Teams Plus is $24 or $32 (Calendly pricing). English only, beta.

Pick it if: you already use Calendly and mostly book one-on-one meetings.

Also available (smaller assistants, not ranked)

Carly

• How it works. “Just CC Carly. She’ll take care of the rest.” (Carly). It works over email, SMS and Slack, with Google and Microsoft calendars (Carly pricing).
• Features. Group scheduling, booking links and polls.
• Price. Personal is $35 a month with 200 credits. A custom domain is Enterprise only.
• Security: no certifications or training policy listed.

Sarra

• How it works. “Sarra is an AI scheduling assistant you CC on an ordinary email,” with Google or Microsoft calendars (Sarra).
• Price. Free has 3 meetings a month. Silver is $15 per seat per month billed annually ($180 a year) for 20 meetings, the same per-seat price as Skej Pro.
• Groups. The FAQ lists up to 5 attendees on Gold and 10 on Platinum (Sarra pricing).
• Privacy. Sarra says your data “is not used to train AI models,” and “Sarra is not currently SOC 2 certified.”

Ari by JustCC

• How it works. Add ari@justcc.to; it “books the first slot everyone agrees on.” Google Calendar and Microsoft 365 (JustCC).
• Price. Free is 10 meetings in total. Basic is $24 a month flat with “Unlimited meetings.” Premium is $39.
• What it reads. It “only ever sees the threads you CC it on.”
• Security: no certifications listed.

Not quite cc assistants (yet)

• Lindy. Its docs label cc-based scheduling “(Coming Soon)” (Lindy docs).
• Cal.ai (Cal.com). A free assistant you email from your own address to check your week or book, cancel and reschedule. It’s built around you emailing it, not around being cc’d on a guest thread (Cal.ai app). Its listing doesn’t say whether it emails an external guest on its own.
• Gemini in Gmail (“Help me schedule”). It inserts suggested times while you write, but you send the email (Google help).
• Copilot in Outlook (“Schedule with Copilot”). It drafts an invite from a thread for you to review and send (Microsoft support).
• Scheduler AI. Its homepage showed placeholder “Lorem ipsum” text and a banner saying part of the product is “now part of Synapsa” (Scheduler AI). Its pricing page says it is “working to obtain SOC 2” (Scheduler AI pricing). We’d wait.

Comparison table

All facts are from each vendor’s pages, linked above. “Not stated” means the vendor’s pages don’t say.

Related reading

• The best AI scheduling assistants of 2026, ranked: A ranked roundup; OpenAssistant is first, Reclaim is the best free start, Calendly the best booking link and Howie the pick for texting.
• Our Howie review: Pricing, strengths, weaknesses and who Howie is for, with alternatives.
• How to delegate your calendar to an AI assistant: Write your rules first, grant the least access that works, roll out in stages and keep the calls only you should make.
• How to let AI email on your behalf: A staged plan: drafts only, then low-stakes sends, then a delay, then send and report.
• How EAs use AI to support several executives: A step-by-step playbook for assistants who support more than one executive.

Frequently asked questions

What is an AI scheduling assistant you cc?

It is an AI with its own email address. You add it on cc, and it reads the thread and your calendar, proposes times to the other person, handles the replies, follows up and sends the invite. The other person installs nothing and clicks no link.

Which cc assistant is best?

On public information we rank OpenAssistant first for its controls, groups, channels and Coordinator Mode. Blockit has the best free plan with a flat meeting count, Howie takes iMessage and SMS, and Clara lists Exchange.

Which cc assistant lets me approve messages first?

OpenAssistant lets you set autonomy per action: Manual, Confirmation Window or Autonomous. Blockit lets you choose from reviewing everything to full autopilot. Skej has no send-approval step.

Is there a free assistant I can cc?

Yes. Blockit’s free plan covers 15 meetings a month. OpenAssistant’s Starter plan is free with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month.

Try OpenAssistant

If you want an assistant you can cc, text or message in Slack, try OpenAssistant. Starter is free, and Pro and Team prices are on the pricing page.