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Square First Week Setup

Square is the fastest processor to set up - you can accept payments in 15 minutes. But taking 2-3 hours to configure properly prevents costly mistakes and saves thousands later.

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Why This Matters​

Square is plug-and-play, but you still need to configure:

  • Wrong business info → Disputes go unanswered (can't reach you)
  • No receipt emails → "I don't recognize this" disputes
  • Keyed-in enabled → Staff keys in everything at 3.5% vs swiping at 2.6%
  • No item library → Can't track what sells, can't prove delivery

This checklist takes 3-4 hours total over 3 days. Worth it to prevent problems.

Day 1: Basic Setup (1 hour)​

Task 1: Verify Business Information (15 min)​

Where: Square app → Account & Settings → Business Information

Verify:

  • Legal business name is correct
  • Support phone number works
  • Business address is correct
  • Email is monitored daily

Why it matters: Disputes and important notices go to this contact info. Wrong email = missed chargebacks = auto-lose.

Task 2: Set Up Square Reader (30 min)​

What you need:

  • Square Reader (magstripe, chip, or contactless)
  • Charged and paired to your phone/tablet

Steps:

  1. Download Square POS app
  2. Pair reader via Bluetooth
  3. Process test transaction ($1.00 to yourself)
  4. Refund test transaction
  5. Verify everything works

Why it matters: Don't discover broken reader during first customer transaction. Test beforehand.

Task 3: Customize Receipt Settings (15 min)​

Where: Square app → Settings → Receipts

Configure:

  • Email receipts: ON
  • SMS receipts: Optional
  • Printed receipts: Only if you have printer
  • Add return policy to receipt footer
  • Add support email/phone

Why it matters: Email receipts reduce "I don't recognize this" disputes by 20-30%.

Day 2: Inventory and Items (1.5 hours)​

Task 4: Create Item Library (1 hour)​

Where: Square app → Items

For each product/service:

  • Name (appears on receipts)
  • Price
  • SKU (optional but recommended)
  • Category
  • Tax settings

Why create items vs open pricing:

  • Track what sells (reporting)
  • Prove delivery for disputes ("They bought X on Y date")
  • Faster checkout (tap item vs typing price)
  • Tax automation

Start with top 10-20 items. Add rest over time.

Why it matters: "They bought PRODUCT X" wins disputes. "They bought something" doesn't.

Task 5: Set Up Categories (30 min)​

Where: Items → Categories

Create categories:

  • For retail: By product type (shirts, pants, accessories)
  • For restaurants: By meal type (breakfast, lunch, drinks)
  • For services: By service type (haircut, color, treatments)

Why it matters: Reports by category show what's profitable. Chargebacks by category show what's disputed most.

Day 3: Fraud and Risk Settings (1 hour)​

Task 6: Configure Fraud Prevention (30 min)​

Where: Square app → Settings → Account & Settings → Security

Square's built-in fraud protection:

  • Enabled by default (can't disable)
  • Automatically flags suspicious transactions
  • No configuration needed

What YOU can configure:

  • CVV verification: Recommended ON for keyed transactions
  • Address verification (AVS): Recommended ON for CNP
  • Decline high-risk: Let Square handle this automatically

For card-present: Fraud is rare. Don't over-configure.

For Square Online (e-commerce): Verify fraud tools are enabled.

Task 7: Disable or Limit Keyed Entry (30 min)​

Where: Square app → Settings → Checkout

Why this matters:

  • Swiped/dipped/tapped: 2.6% + $0.10
  • Keyed-in manually: 3.5% + $0.15
  • Difference: 0.9% + $0.05 = ~$1 per $100

At 100 keyed transactions/month: That's $100/month wasted.

Configuration:

  • Require explanation for keyed entry (if possible)
  • Train staff: "Use the reader, don't key in"
  • Only key when customer doesn't have physical card

Exception: Restaurants taking phone orders need keyed-in enabled.

Ongoing Best Practices (Post-Week 1)​

Task 8: Set Up Employee Permissions (if applicable)​

Where: Square app → Team → Employees

Create staff accounts with permissions:

  • Cashier: Process sales, refunds (no reporting)
  • Manager: Full access except bank settings
  • Owner: Everything

Why it matters: Staff can't steal if they don't have refund access. Separate permissions protect you.

Task 9: Enable Tipping (if applicable)​

Where: Checkout settings → Tipping

For restaurants/services:

  • Enable tipping
  • Set suggested amounts (15%, 18%, 20%)
  • Choose when to prompt (before or after payment)

For retail: Usually skip

Task 10: Review First Week of Transactions​

End of Week 1, review:

  1. Total volume: $______
  2. Transaction count: ______
  3. Chargebacks: ______ (should be 0 in first week)
  4. Refunds: ______ (under 5% is normal)
  5. Keyed-in %: ______ (should be under 10%)

Red flags:

  • 20% keyed-in: Retrain staff

  • 5% refunds: Product or service issue

  • Any chargebacks in Week 1: Investigate immediately

Square Online Setup (If Applicable)​

If using Square for e-commerce in addition to card-present:

Additional Day 1 Tasks:​

Task 11: Set Up Square Online Store (1 hour)

  • Configure shipping zones and rates
  • Add product photos and descriptions
  • Test checkout flow end-to-end
  • Verify email confirmations send

Task 12: Configure Shipping Confirmations (30 min)

  • Enable automatic shipping confirmation emails
  • Include tracking numbers
  • Add "Order shipped" customer communications

Why it matters: Shipping confirmations reduce "not received" disputes by 40-60%.

Square vs Stripe: Setup Differences​

Setup AreaSquareStripe
DescriptorAuto-set from business nameMust configure manually
Fraud rulesAutomatic, can't customize muchFully customizable
Dispute alertsNot availableRDR available
WebhooksAvailable but not requiredCritical for automation
POSFull POS included freeSeparate terminal/SDK

Square is simpler: Less configuration needed, but also less control.

Common Square First-Week Mistakes​

Mistake 1: Not Training Staff on Reader Usage​

Symptom: Staff keys in every transaction (3.5% + $0.15 vs 2.6% + $0.10)

Cost: $500-1,000/month wasted on keyed-in fees

Prevention: 15-minute training: "Use the reader for every transaction unless customer doesn't have card"

Mistake 2: No Item Library​

Symptom: Everything processed as "Sale" with no item details

Cost: Can't prove what was purchased in disputes, can't track inventory

Prevention: Spend 1 hour building item library before opening

Mistake 3: Missing Email Receipts​

Symptom: Customers don't have proof of purchase, dispute charges

Cost: 15-20% higher "I don't recognize" disputes

Prevention: Enable email receipts on Day 1

Mistake 4: Wrong Tax Settings​

Symptom: Over or under-collecting sales tax

Cost: Compliance violations discovered months later

Prevention: Verify tax rate matches your state/locality

Mistake 5: Instant Deposits Addiction​

Symptom: Using 1.5% instant deposits daily

Cost: $150 per $10K instant = $600/month if doing $40K

Prevention: Use standard deposits (1-2 days). Only instant for emergencies.

Test to Run​

Square first-week audit:

Day 7 review:

  1. Process a test transaction, check receipt format
  2. Calculate keyed-in percentage: ____% (should be under 10%)
  3. Review first week reports in Square dashboard
  4. Check for any disputes (should be 0)
  5. Verify staff can operate reader without help

Success criteria: Receipts look professional, keyed-in under 10%, staff trained, no disputes.

Scale Callouts​

First week ($5K-10K):

  • Manual POS mode fine
  • Owner handles all transactions
  • Simple item library (10-20 items)

First month ($50K-100K):

  • Add staff if needed
  • Expand item library
  • Review metrics weekly

First quarter ($150K-300K):

  • Consider Square Plus for inventory features
  • Hire dedicated staff
  • Daily reporting review

Beyond $500K:

  • Evaluate if Square pricing still competitive
  • Consider traditional processor for lower rates
  • But Square POS is still excellent

Where This Breaks​

  1. High volume immediately: If you're processing $100K+ in first week, you'll trigger Square's risk review. Prepare for potential hold.

  2. Online + in-person: If you're using Square for both, setup is 2x (POS + Online). Budget 6-8 hours total.

  3. Multiple locations: Each location needs separate setup, hardware, training. Multiply timeline by location count.

  4. High-ticket items ($500+): Square holds high-ticket payments for 24-72 hours. Warn customers about potential delays.

  5. Subscription/recurring: Square's card-on-file rate is 3.5% + $0.15 (expensive). Consider Stripe for recurring.

Next Steps​

Completed first week?

  1. Read Square Processor Profile for optimization
  2. Review Operations Checklist for ongoing tasks
  3. Monitor weekly and adjust

Need additional features?

  1. Loyalty program - Square Loyalty setup
  2. Inventory management - Track stock
  3. Employee management - Time tracking

Growing out of Square?

  1. Calculate Total Cost Model at current volume
  2. Compare to negotiated rates with traditional processors
  3. See Processor Switch Checklist

See Also​