Square Feature Request: Native Delivery Route Management

[JTPets]

Executive Summary

Square merchants with local delivery fulfillment currently lack integrated route optimization and proof-of-delivery tools. We've built a third-party solution demonstrating the workflow, but this functionality belongs natively in Square's ecosystem where it can leverage existing order data, customer profiles, and POS integration seamlessly.

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The Problem

Merchants offering local delivery (pet stores, florists, bakeries, pharmacies, etc.) face a fragmented workflow:

1. Orders come into Square with delivery fulfillments
2. No route optimization - drivers manually sequence stops or use separate apps (Google Maps, Circuit, Routific)
3. No proof of delivery - no native way to capture delivery photos tied to orders
4. No driver-specific view - drivers use generic Square POS or paper manifests
5. Manual status updates - marking orders complete requires switching between apps
6. No delivery analytics - no visibility into delivery performance, times, or patterns

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Proposed Solution: Square Delivery Manager

Core Features

1. Delivery Queue (Order Manager Enhancement)

• Filter orders by fulfillment type: DELIVERY, SHIPMENT, PICKUP
• Visual status: Pending → On Route → Delivered → Completed
• Batch actions: Add to route, skip, reschedule
• Auto-geocoding of delivery addresses (already have address data)

2. Route Optimization

• One-click route generation using traveling salesman optimization
• Configurable start/end locations (store, driver home, etc.)
• Same-day cutoff time setting (e.g., "no new orders after 2pm for today's route")
• Manual drag-and-drop reordering
• Integration: OpenRouteService, Google Maps, or HERE APIs (merchant provides API key or Square provides pooled access)

3. Driver Mobile View (Square POS App or Standalone)

• Today's route with turn-by-turn navigation handoff
• Stop-by-stop order details (items, notes, customer phone)
• One-tap actions:
  • "Navigate" → Opens Maps app
  • "Call Customer" → Direct dial
  • "Mark Delivered" → Captures POD photo
  • "Skip" → With reason code (not home, refused, weather)
• Offline capability for rural deliveries

4. Proof of Delivery (POD)

• Camera capture tied to order
• GPS coordinates embedded in photo metadata
• Timestamp verification
• Customer signature option (optional)
• Auto-attach to order in Square Dashboard
• Configurable retention period (30/90/180 days)

5. Customer Notifications (Twilio/Square Messages Integration)

• "Your order is out for delivery" (when route starts)
• "Driver is 2 stops away" (proximity trigger)
• "Delivered!" with POD photo (optional)
• Delivery feedback request

6. Analytics Dashboard

• Deliveries per day/week/month
• Average delivery time
• On-time delivery rate
• Driver performance comparison
• Delivery heatmap (popular areas)
• Failed delivery reasons

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Quality of Life Enhancements

For Merchants

• Recurring delivery schedules - Customers on weekly/monthly delivery programs
• Delivery zones - Define serviceable areas with different fees
• Driver assignment - Multiple drivers with separate routes
• Capacity limits - Max deliveries per route based on vehicle size
• Priority orders - Rush/VIP customers flagged for earlier slots

For Drivers

• Estimated earnings - If using tipped delivery model
• Break scheduling - Insert breaks into long routes
• Return-to-store stops - For restocking mid-route
• Customer preferences - "Leave at door", "Ring bell", "Gate code: 1234"

For Customers

• Live tracking - Real-time driver location (like DoorDash/UPS)
• Delivery window selection - At checkout, pick 2-hour windows
• Reschedule self-service - Customer portal to change delivery date
• Delivery instructions - Saved to customer profile for future orders

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Technical Implementation Notes

What Square Already Has

• ✅Order data with fulfillment types
• ✅Customer addresses and phone numbers
• ✅Webhook infrastructure (order.created, order.updated, order.fulfillment.updated)
• ✅Square Messages for SMS
• ✅Team Management for driver accounts
• ✅Mobile POS app infrastructure

What's Needed

• 🔧Route optimization API integration (OpenRouteService is free/open, or license HERE/Google)
• 🔧POD photo storage (already have image infrastructure for items)
• 🔧Driver mobile UI (new screen in Square POS app or Square Staff app)
• 🔧Geocoding service (Google Maps API, already likely in use)

API Additions

POST /v2/fulfillments/delivery/routesGET  /v2/fulfillments/delivery/routes/{route_id}
POST /v2/fulfillments/delivery/routes/{route_id}/optimize
POST /v2/fulfillments/{fulfillment_id}/proof-of-delivery
GET  /v2/fulfillments/{fulfillment_id}/proof-of-delivery

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Competitive Landscape

Feature Square (Current) Shopify Toast Our Add-on

Delivery Orders	✅	✅	✅	✅
Route Optimization	❌	❌(3rd party)	❌	✅
Proof of Delivery	❌	❌	❌	✅
Driver Mobile App	❌	❌	❌	✅
Customer Tracking	❌	❌	❌	🔜
Delivery Analytics	❌	Basic	❌	🔜

Opportunity: First major POS platform with native local delivery management would capture significant market share in delivery-heavy verticals (florists, pet stores, pharmacies, meal prep, bakeries).

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Merchant Validation

We've deployed this functionality for JTPets (pet food delivery) and validated:

• 17+ orders synced from existing Square orders in first test
• Route generation working with OpenRouteService API
• POD capture with 180-day retention
• Driver view mobile-optimized and functional
• Webhook integration for real-time order ingestion

Merchants are actively asking for this. The workaround ecosystem (Circuit, Routific, OnFleet) proves demand exists but fragments the Square experience.

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Recommended Rollout

Phase 1: Delivery Queue + Manual Route Creation

• Filter/sort delivery orders
• Drag-and-drop route building
• Basic driver checklist view

Phase 2: Route Optimization + POD

• One-click optimization
• Photo capture tied to orders
• GPS verification

Phase 3: Customer Experience

• Delivery notifications
• Live tracking
• Delivery window selection at checkout

Phase 4: Analytics + Advanced Features

• Performance dashboards
• Multi-driver support
• Recurring deliveries
• Delivery zones

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Contact

This feature request is based on a working prototype built on Square's APIs. Happy to demo or provide technical consultation.

Built by: JTPets / Square Dashboard Addon Tool
Date: January 2026

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"Square handles everything from sale to fulfillment—except the last mile. Let's fix that."

[nika]

@JTPets Insane! You are BUSY building lately, and I love it. I just shared this with our Restaurants team. 👊

[JTPets]

My own Necessity has driven several tools being invented for JT Pets. I am just sharing the POC and code openly in hopes of a single tool rather than a fragmented one for me and my team.

Https://github.com/JTPets/SquareDashboardTool

[driche01]

@JTPets , I just wanted to say thank you for taking the time to not only share this idea, but to draft out the idea so thoughtfully. This is a strong example of how sellers can help co-build Square in creative, high-impact ways.

Really appreciate you being such an engaged and innovative member of the Square ecosystem...please keep the ideas coming!!

-Square Product Team

[JTPets]

Please check out my full suite of tools im developing in open-source for my own needs https://github.com/JTPets/SquareDashboardTool