⚖️Side-by-Side Comparison

Square vs Reply: Which is Better in 2026?

We've compared 2 tools across pricing, features, ratings, and reviews to help you make an informed decision. No paid placements — just facts.

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Feature
Square logo
Square

CRM & Sales

Reply logo
Reply

CRM & Sales

RatingNo reviews yetNo reviews yet
Pricing
  • Square Register (2nd generation):$899/one-time
  • Square Handheld:$399/one-time
  • Square Terminal:$299/one-time
  • Square Stand:$149/one-time
  • Square Reader for contactless and chip:$59/one-time

as of Sep 24, 2026

$49/mo

as of Sep 23, 2026

Pricing ModelPaidPaid
Free Plan
Free Trial
API Available
VerifiedVerified
Founded2009—
HQSan Francisco, CA—
Team Size1000+—
Platforms
WebiOSAndroid
—
Top Integrations
QuickBooksXeroMailchimpWix
—
Key Features
  • Point of sale
  • Team management
  • Marketing & loyalty
  • Cash flow control
  • Hardware
  • +2 more
  • Multichannel Sequences
  • Jason AI SDR
  • AI Sales Assistant
  • B2B Contact Database
  • Email Health Check
  • +3 more
Description

Square (now Block) provides everything small businesses need to start, run, and grow. From iconic POS hardware to online stores, payroll, and banking, Square serves millions of sellers globally with simple, transparent pricing.

Reply.io is an AI-powered sales engagement platform that automates multichannel outreach across email, LinkedIn, calls, and SMS, covering the full cycle from sourcing leads to booking meetings. It's built for B2B sales teams, SDRs, and agencies who want to run and scale cold outreach, and its stand-out is Jason, an AI SDR agent that can define an ICP, source prospects, write personalized sequences, and even handle replies end to end. A built-in B2B contact database and email deliverability/health tooling round out the workflow.