Best AI scheduling for client appointments

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

Short answer: Acuity Scheduling is an assistant we recommend for paid client bookings, Clio Scheduler fits law firms already on Clio, and OnceHub is the pick if you need a HIPAA BAA add-on. If your client meetings start in email threads with busy executives, Skej (ours) takes the back-and-forth, but it has no intake, payments or BAA.

What client scheduling needs that ordinary scheduling doesn’t

When clients book you, the meeting is the start of paid work. Look for:

1. Intake. Questions answered before the meeting: the matter, account type, conflicts information.
2. Payments or deposits at booking, so no-shows cost something.
3. Reminders by email and text, to cut no-shows.
4. Compliance. Health-related practices may need a signed HIPAA business associate agreement (BAA). Financial firms may have record-keeping duties. Law firms want the booking to land in their practice management system.

This article isn’t legal or compliance advice. A vendor saying it supports HIPAA or helps with FINRA doesn’t make your use compliant. Check with your compliance team or bar association, and read each vendor’s terms.

Our ranking

Based on published intake, payment, reminder and compliance features, considered qualitatively for this use case.

1. Acuity Scheduling: the most complete client booking tool

Best for: solo practitioners and small firms who take paid or pre-qualified bookings.

• On every plan. Custom intake forms, plus payments and deposits through Stripe, Square, PayPal or Venmo (Acuity pricing).
• Standard and Premium add: text reminders, packages and memberships.
• Price. Starter is $16 a month on annual billing ($20 monthly), Standard $27 ($34), Premium $55 ($69). There’s a 7-day free trial and no free plan.
• HIPAA. The pricing page lists “Sign BAA for HIPAA compliance” on Premium; the help center says Premium or Powerhouse. Acuity itself says enabling HIPAA features “alone isn’t enough to make you HIPAA compliant.” Its help center says HIPAA-enabled accounts lose some features, including invoices and calendar sync with Office 365, Outlook.com, Exchange and iCloud. You must also keep protected health information out of notifications yourself (Acuity HIPAA help).

2. Clio Scheduler: for law firms already on Clio

Best for: firms using Clio Manage.

• How you get it. Clio’s booking feature comes with Clio Grow, which is an add-on and is “included in Elite and Elite Work” (Clio pricing). Clio Manage plans start at “$49 USD per user per month.”
• Features. Paid bookings need Clio Payments. Bookings sync to the Clio Manage calendar, and to Outlook and Google. You can set up to five automated text reminders. Booking rules can block same-day, back-to-back or last-minute bookings. Clio’s AI can qualify leads, run conflict checks and move prospects to a booking (Clio appointment bookings).
• Security. Clio claims SOC 2 Type II.

Watch out for: the Clio Grow add-on price isn’t published, so you’ll need a demo.

3. OnceHub: compliance add-on for regulated firms

Best for: firms that want a BAA (health) or saved copies of client notifications (record-keeping) from their scheduling tool.

• Compliance add-on. It includes HIPAA BAAs, costs $5 per seat per month on annual billing or $6 monthly, and is included in Enterprise. OnceHub says it gives regulated industries tools for “GDPR, FINRA, HIPAA, and FERPA” (OnceHub pricing). A separate Guest Communication Compliance add-on saves a copy of every notification sent to guests. The FINRA mention is OnceHub’s own claim; whether it meets your firm’s record-keeping duties is for your compliance team to decide.
• Plans. Schedule is $10 per seat per month on annual billing, with Stripe payments, booking forms, and Salesforce and HubSpot integrations. Route ($19) adds routing forms and round robin.
• Certifications. SOC 2 Type 2 and PCI DSS Level I are marked on every plan, including the free Basic plan.

4. Calendly: polished, but not for health data

Best for: consultants and coaches without health-data concerns.

• Payments and intake. Standard ($10 per seat per month on annual billing) adds Stripe and PayPal payments and reminders (Calendly pricing). Calendly can collect deposits and sell packages (Calendly payments). Each event type can ask up to 10 custom questions on any plan (Calendly help).
• Certifications. SOC 2 Type 2, ISO/IEC 27001 and PCI (Calendly security).
• HIPAA. “Calendly is not currently designed for HIPAA compliance,” and BAAs “are not applicable” (Calendly help). Don’t use it for protected health information.

5. Microsoft Bookings: included if you’re on Microsoft 365

Best for: firms on Microsoft 365 that don’t take payments at booking.

• What it does. Personal and shared booking pages, with online appointments that get a Teams link. It’s available in Business Basic, Standard and Premium and many enterprise plans (Microsoft Learn). Business Basic is $7 per user per month paid yearly (Microsoft 365 plans).
• Payments. “There’s no payment support in Bookings” (Bookings FAQ).

6. YouCanBookMe: simple and affordable

• Free plan. Includes Stripe payments (“Additional fees apply”) and custom booking questions.
• Paid plans. Individual is $9 a month and Professional $13 on monthly billing, less on yearly or two-year terms. Professional adds workflows for follow-ups and no-show handling (YouCanBookMe pricing).

Watch out for: its site states no HIPAA or BAA position, and its terms restrict storing others’ medical data (YouCanBookMe terms).

7. Setmore: cheapest per user

• Price. Pro is $5 per user per month on annual billing or $12 monthly. Each staff calendar counts as a user (Setmore pricing).
• Features. Payments through Square, Stripe, PayPal and LawPay. Deposits on Pro. SMS reminders on Pro.

Watch out for: a BAA is only offered through Setmore Health, a separate account type you must choose when you sign up on Pro or Team; it can’t be added later (Setmore Health, Setmore pricing). Setmore’s general terms say standard Setmore “is not currently HIPAA compliant” (Setmore terms). Setmore also says signing the BAA alone doesn’t make you compliant.

8. Skej (our product): for the email back-and-forth, not intake

Best for: consultants and advisors whose client meetings start in email threads with executives who won’t fill in a booking form. Skej has processed millions of meetings.

• How it works. You cc an assistant on a client thread, and it proposes times, follows up and books (Skej).
• Booking link. Guests can chat with the assistant to find a time, and can reschedule or cancel by replying to the confirmation (Skej booking link help).
• Protecting your calendar. Buffers and daily meeting caps (Skej buffers help).
• Price. Pro is $15 per user per month on annual billing (Skej pricing).

Where others do better, plainly:

• No intake, payments or texts. Skej’s site lists no intake forms, no payments or deposits, and no client text reminders. It sends reminders to you, the host.
• No BAA. No HIPAA BAA is offered on its site.
• No practice-management link. Its site lists no connection to practice management systems like Clio.

For most client-booking needs, any tool ranked above it is the better choice.

Comparison table

All facts are from each vendor’s pages linked above. “Not listed” or “Not confirmed” means the vendor’s pages do not say.

Related reading

• AI scheduling tools for sales teams: Chili Piper for large inbound teams on Salesforce, Calendly Teams for smaller teams.
• AI interview scheduling tools for recruiters: GoodTime for large teams, and the scheduling inside Greenhouse or Ashby as a starting point.
• Scheduling links vs AI assistants: When a link is better, when an assistant is better and when to use both.
• 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.
• 21 security questions to ask before giving AI your inbox: Questions to put to the vendor, answers that should worry you and settings to check yourself.

Frequently asked questions

What is the best appointment scheduling software for lawyers?

Clio Scheduler fits firms already on Clio Grow. Acuity Scheduling is the most complete standalone option, with intake forms and payments on every plan. Neither guarantees compliance, so check with your bar association.

Which scheduling tool offers a HIPAA BAA?

Acuity lists a BAA on Premium. OnceHub offers one in a compliance add-on at $5 per seat per month on annual billing. Setmore offers one only through Setmore Health. Calendly says it is not designed for HIPAA compliance.

Can I take payments when clients book?

Yes, with Acuity (Stripe, Square, PayPal or Venmo), Calendly Standard and up, OnceHub Schedule, and Setmore. Microsoft Bookings has no payment support.

Can Skej handle client appointments?

Skej handles the email back-and-forth: you cc an assistant on a client thread and it proposes times and books. It lists no intake forms, payments, client text reminders or BAA.

Try Skej

If your client meetings start in email threads, try Skej. Use it alongside an intake and payments tool if you need those.