Calendly Alternative With File Uploads: Complete Guide

TL;DR:

• Calendly doesn’t support file uploads during booking - you’ll need an alternative if documents are part of your process.
• Sprintful combines scheduling + file collection + automated workflows in one place.
• Collecting files during booking reduces back-and-forth and helps prevent no-shows by setting expectations early.
• Mobile-optimized upload flows matter because a large share of bookings start on phones.

At a Glance: Calendly vs File Upload Solutions

👉 Try Sprintful’s file-upload demo

Why Calendly Fails at File Collection (And What It Costs You)

Calendly is built for simplicity - but simple isn’t always better for operations.

When you can’t collect files during booking, here’s what typically happens:

• Higher risk of no-shows because clients arrive unprepared
• Prep delays while your team chases documents
• More back-and-forth emails before appointments can proceed
• Lost revenue when services require documents up front

Industries That Need File Collection During Booking

Healthcare & Wellness
Insurance cards, medical history, intake forms
    Sprintful lets you collect and store files securely and route them where your team needs them.

Legal Services
Case documents, contracts, ID verification
    Use conditional logic to show different forms based on case or matter type.

Financial Services
Tax docs, bank statements, financial records
    Collect sensitive documents securely and keep your workflow organized.

Consulting & Professional Services
Project briefs, NDAs, company info
   Prefill client data and streamline pre-meeting preparation.

Fitness & Beauty
Health questionnaires, waivers, before photos
    Mobile-first uploads keep on-the-go clients moving.

See how Sprintful handles your industry (industry pages coming soon).

Why Sprintful Beats Other Calendly Alternatives

1) File Uploads That Actually Work on Mobile

Other platforms bolt file uploads onto desktop-first forms. Sprintful is designed to keep mobile users moving:

• Fast, reliable uploads with clear progress indicators
• Image handling that keeps uploads snappy
• Touch-optimized interface that feels natural on a phone

2) Conditional Logic & Per-Appointment Routing

Many tools treat every appointment the same. Sprintful adapts:

• New clients see intake + required uploads
• Returning clients skip redundant steps
• Different services can request different files
• Routing per appointment type keeps your workflows clean

3) Integrations That Fit Real-World Stacks

Avoid brittle workarounds. Sprintful connects cleanly to the tools you already use:

• Calendars: Google Calendar, Outlook, MS Exchange
• Video: Zoom, Google Meet, Microsoft Teams
• Payments: Stripe
• Team comms: Slack
• Automation: Zapier

Dev-friendly: Webhooks and Custom NodeJS events for anything bespoke

How Sprintful’s File-Upload System Works

Step 1: Smart Form Creation

Our form builder helps you design the right flow for your business. Example: Dental Practice Setup

• ✅ Auto-suggests common items (insurance cards, medical history, emergency contact)
• ✅ Sets appropriate file limits (10MB per file)
• ✅ Configures a mobile-friendly upload sequence
• ✅ Uses secure storage and routing options

Step 2: Intelligent Routing

Files don’t disappear into inboxes - they go where your team needs them:

• Notify staff in Slack
• Trigger actions via Zapier
• Send data to your systems with Webhooks or Custom NodeJS events

Step 3: Automated Follow-up

When something’s missing, Sprintful helps you close the loop:

• Smart reminders at sensible times
• Escalation paths for urgent appointments
• Staff notifications for incomplete files
• Client links for easy post-booking uploads

👉 Watch the 3-minute demo →

Migration Guide: Switch From Calendly in One Week

Day 1–2: Set Up Your Sprintful Account

• Start your 7-day trial (no credit card). 
• Import your Calendly event types.
• Configure file-upload requirements per service.
• Test the mobile flow on your phone.
  

Day 3–4: Configure Integrations

• Connect your calendar (Google, Outlook, Exchange).
• Enable Zoom/Meet/Teams.
• Add Slack notifications.
• Set up Zapier, Webhooks, or Custom NodeJS for routing.

Day 5: Staff Training & Testing

• 15-minute team walk-through.
• Test end-to-end booking.
• Verify files reach the right destinations. 

Day 6–7: Go Live

• Update booking links on your site and email signatures.
• Notify existing clients about the upgrade.
• Monitor file-completion and booking completion.

Get started today
 👉 Sign up for a free trial →

Pricing: Simple & Affordable

Sprintful: $9/month • 7-day free trial
No surprise add-ons for file collection. Get scheduling, file uploads, and automation in one place.

👉 See pricing →

Frequently Asked Questions

How is Sprintful different from Acuity or Calendly?
Sprintful is built specifically for workflows that require documents, with conditional logic, per-appointment routing, and developer-friendly hooks.

What if clients don’t upload files during booking?
Sprintful sends smart reminders and gives clients a simple link to finish uploading later.

Are uploads secure?
Yes - uploads are encrypted in transit and at rest, and you control where files go using Slack, Zapier, Webhooks, or Custom NodeJS.

What’s the largest file size I can accept?
Up to 10MB per file. For larger needs, we can discuss custom approaches via integrations.

Can I customize the upload interface?
Absolutely. Use your brand, custom domain, and tailored messages.

How quickly can I switch from Calendly?
Most teams migrate in a few days. However it is possible to get up & running in a few minutes. 

Do you integrate with my stack?
Likely yes - connect calendars, video tools, Stripe, Slack, Zapier, or wire up Webhooks/Custom NodeJS for bespoke systems.

Start Collecting Files Today (Risk-Free)

Stop losing time to document chaos. Sprintful’s file-upload system is built for teams that need reliable file collection - not just basic scheduling.

Ready to upgrade from Calendly?

🎯 Start your 7-day trial  -  full access, no credit card