Softwr

Software · head to head

Calendly vs Expensify

Calendly logo

Calendly

Software

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Expensify logo

Expensify

Software

Expense management for receipts, bills & more

From
$5/month
Rated
-
Full reviewWebsite

The short version

  • Only Calendly has a free tier, so it costs nothing to try first.
  • Each has a real cost: Calendly the free plan allows one event type and one calendar connection, so it cannot handle different meeting formats; Expensify minimal offline expense entry capabilities hamper use in areas with unstable internet
  • They diverge on capability: Calendly covers Calendar sync, Expensify covers SmartScan receipts.

Where they differ

Only the attributes on which Calendly and Expensify actually diverge.

Attributes where Calendly and Expensify differ
AttributeCalendlyExpensify
Starting priceFree$5/month
Free tierYesNo
Founded20132008

Identical on both: pricing model (Unknown), platforms (Web, iOS, Android), user rating (Not yet rated), category (Unknown).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Calendly

  • Calendar sync
  • Automated scheduling
  • Custom availability
  • Time zone detection
  • Reminder emails
  • Buffer time
  • Meeting polls
  • Embed on website

Only in Expensify

  • SmartScan receipts
  • Expense reports
  • Corporate cards
  • Reimbursements
  • Travel booking
  • Mileage tracking
  • Multi-currency
  • Real-time syncing

Both cover

  • Slack
  • SOC2
  • GDPR

What people use each for

The jobs each tool is most often brought in to do.

Calendly

  • Sales meetingsnot Expensify
  • Interview schedulingnot Expensify
  • Customer callsnot Expensify
  • Office hoursnot Expensify
  • Webinar registrationnot Expensify

Expensify

  • Expense reportingnot Calendly
  • Receipt managementnot Calendly
  • Travel expensesnot Calendly
  • Corporate card managementnot Calendly
  • Reimbursementsnot Calendly

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Calendly

  • The free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
  • Automated reminders and multiple calendars need Standard at $10 per seat per month
  • Round-robin routing, lead qualification and Salesforce integration require Teams at $16 per seat per month
  • SAML single sign-on, audit logs and domain control are Enterprise only, starting at $15,000 a year
  • Advertised prices are the annual rates

Expensify

  • Minimal offline expense entry capabilities hamper use in areas with unstable internet
  • OCR receipt data extraction requires manual review and correction for accuracy
  • Per-user pricing model increases costs for larger organizations

Pricing, plan by plan

Calendly

Free
  • FreeFree
    • 1 event type
    • 1 calendar connection
    • Basic confirmation email
  • Standard$10/month
    • Unlimited event types
    • Multiple calendars (up to 6)
    • Integrations with HubSpot, Mailchimp, Stripe, PayPal
  • Teams$16/month
    • All Standard features
    • Salesforce integration
    • Round-robin meetings
  • Enterprise$15000/year
    • All Teams features
    • Salesforce routing lookup
    • Microsoft Dynamics 365

Expensify

$5/month

No published plan breakdown. See the Expensify review.

Which should you pick?

Choose Calendly if

  • You need calendar sync.
  • You want to start without paying.
  • You work on Web, iOS, Android.
  • You also want automated scheduling.
Calendly review

Choose Expensify if

  • You need smartscan receipts.
  • You work on Web, iOS, Android.
  • You also want expense reports.
Expensify review

Questions people ask

Is Calendly or Expensify better?
Neither clearly leads. Calendly starts at Free and Expensify at $5/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Expensify?
Calendly has a free tier; the other does not. Paid plans start at Free for Calendly and $5/month for Expensify.
Does Calendly or Expensify run on more platforms?
Both run on Web, iOS, Android, so platform support will not decide this one for you.
Can I use Calendly for free?
Yes. Calendly has a free tier, so you can try it without paying. Expensify starts at $5/month.
What is Calendly best used for?
Calendly is most often used for sales meetings, interview scheduling, customer calls, office hours. Of those, sales meetings and interview scheduling are not what Expensify is typically brought in for.
What can Calendly do that Expensify cannot?
Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Expensify covers SmartScan receipts, Expense reports, Corporate cards, Reimbursements. Both handle Slack, SOC2, GDPR.

Answered from the vendors’ own pages

Calendly: Does the free tier include automatic reminders?

No. The free plan only includes a basic confirmation email when someone books. Automated reminder workflows, SMS reminders, and follow-up sequences require the Standard plan ($10/month or higher).

Source
Expensify: How does Expensify capture receipts?

Expensify uses SmartScan technology with OCR to automatically extract data from receipt images, reducing manual data entry. Users can photograph receipts with their phone to quickly create expense entries.

Source
Calendly: Can I offer multiple meeting types on the free plan?

Only one event type can be active at a time. You can create multiple event types, but only one booking link works simultaneously. Switching between different meeting lengths requires manually activating another event type.

Source
Expensify: What reimbursement methods does Expensify support?

Expensify supports ACH reimbursement via direct deposit after setting up a direct deposit account. Next-day reimbursement is available, or standard processing takes 3-5 business days.

Source
Calendly: Does Calendly work with Apple Calendar and iCloud?

No longer for new users. As of August 20, 2024, new users cannot connect iCloud or Apple Calendar. Existing connections continue to work, but Calendly ended support for new Apple Calendar integrations citing Apple's security changes.

Source
Expensify: How does Expensify offline mode work?

Expensify has limited offline capabilities. Users can capture receipts offline, but data syncs when internet connectivity is restored. Full functionality requires online access.

Source
Calendly: What platforms can I use Calendly on?

Calendly is available on Web, iOS, and Android. Browser extensions are available for Safari. There are no dedicated Windows or Mac desktop applications.

Source
Calendly: What does the Standard plan ($10/month) add over free?

Unlimited event types, multiple calendar connections (up to 6), integrations with HubSpot, Mailchimp, Salesforce, Stripe, PayPal, Zapier, and webhooks, plus automated reminders and email sequences.

Source
ShareXLinkedInRedditWhatsAppEmail

Related pages

More on Calendly

More on Expensify

Keep looking

Other head to heads