TMS Software Buyers Guide

Introduction

Choosing TMS software is one of the most consequential decisions a freight forwarder makes. The right system becomes the foundation for growth; the wrong one becomes an expensive anchor that limits what your team can accomplish.

If you’re reading this, you’ve likely already realized you need better technology. Maybe you’ve outgrown spreadsheets. Maybe your current system is showing its age. Or maybe you’re frustrated with complexity and cost after trying to make an enterprise solution work for your mid-market operation.

Here’s what we’ve learned from helping 1,000+ freight forwarders evaluate their options: The most common mistake isn’t choosing the wrong features—it’s choosing a system built for a different type of company.

A global enterprise with 500 employees and offices on four continents has fundamentally different needs than a growing forwarder with 25 people focused on US ocean imports. Yet both might evaluate the same “industry-leading” TMS, with very different outcomes.

“I tried 7 different systems before GoFreight. They were all either too complicated or didn’t understand freight forwarding.” — Janko Wille, CEO, Allround Forwarding Midwest

This guide helps you navigate the TMS landscape by: - Understanding the different categories of TMS software - Identifying which features actually matter for your operation - Evaluating total cost of ownership (not just subscription price) - Asking the right questions during vendor demos - Planning for successful implementation

Whether you’re buying your first TMS or replacing a system that isn’t working, this guide provides the framework for making a confident decision.

→ New to TMS? Read What is TMS? for foundational context.

Understanding TMS Software Categories

Not all TMS platforms are created equal. Understanding the categories helps narrow your evaluation to systems actually designed for your situation.

By Target Market

Enterprise TMS (500+ employees) - Examples: CargoWise, Descartes, SAP TM, Oracle TMS - Characteristics: Comprehensive features, complex configuration, long implementations - Pricing: $500-2,000+/user/month, plus significant implementation fees - Best for: Global enterprises with dedicated IT teams

Mid-Market TMS (15-500 employees) - Examples: GoFreight, Magaya, 3Gtms - Characteristics: Purpose-built for freight forwarding, faster implementation - Pricing: $100-400/user/month, implementation typically included - Best for: Growing forwarders seeking scalable foundation

SMB/Startup TMS (<15 employees) - Examples: Freightos, Flexport (for small shippers), basic quoting tools - Characteristics: Limited functionality, often focused on specific workflows - Pricing: $50-150/user/month - Best for: Very small operations or specific use cases

→ Small operation? See Best TMS for Small Business for right-sized options.

By Primary Function

Full-Service Forwarding TMS Systems designed specifically for freight forwarders and NVOCCs: - Shipment management across modes (ocean, air, ground) - Documentation (BOL, AWB, ISF, commercial invoices) - Accounting with P&L by shipment - Customer portals and visibility

Shipper-Focused TMS Systems designed for companies shipping their own goods: - Carrier procurement and rate shopping - Load optimization - Freight audit and payment - Not ideal for forwarders (missing core forwarding workflows)

Carrier TMS Systems for trucking companies and carriers: - Dispatch and driver management - Fleet optimization - Not designed for forwarder operations

The Fit Problem

The biggest TMS buying mistake: choosing a system designed for a different company type.

Enterprise systems like CargoWise are powerful but require significant resources: > “I’m scared to death every time I see a bill from CargoWise.” — Branch Manager at a mid-size US forwarder

Shipper-focused systems miss critical forwarding features. SMB tools limit growth.

The sweet spot for most growing forwarders: Mid-market TMS platforms built specifically for freight forwarding workflows, with the depth to handle complexity and the simplicity to implement quickly.

→ Compare enterprise vs. mid-market: GoFreight vs CargoWise

Must-Have Features for Freight Forwarders

Feature lists can overwhelm. Here’s what actually moves the needle for forwarding operations.

Tier 1: Non-Negotiable Features

These capabilities are essential for any freight forwarding TMS:

1. Multi-Mode Shipment Management - Ocean (FCL and LCL workflows) - Air freight with HAWB/MAWB handling - Ground/trucking coordination - Ability to handle cross-mode shipments

2. Documentation Generation - Bill of Lading (Master and House) - Air Waybill - Commercial invoices - Packing lists - Arrival notices - Must be auto-populated from shipment data (no re-keying)

3. Rate Management - Store carrier contract rates - Build customer quotes quickly - Convert quotes to bookings without re-entry

“Not loving process from quote→shipment with reentering information” — Common complaint about legacy systems

4. Accounting Integration - Native QuickBooks integration (critical for US forwarders) - P&L by shipment visibility - Accounts receivable/payable tracking - Agent settlement management

5. Tracking & Visibility - Carrier integration for container/flight tracking - Milestone management - Exception alerts - Customer-facing tracking portal

Tier 2: High-Value Features

These differentiate good TMS platforms from basic ones:

1. Customer Portal - Self-service tracking for shippers - Document access and download - Booking requests - Branded with your company identity

2. Customs & Compliance - ISF filing integration - AMS connectivity - ABI interface (for customs brokers) - Denied party screening integration

→ Need customs capabilities? See Customs Brokerage Software Guide.

3. Carrier Connectivity - Direct booking with carriers - Rate retrieval - Container availability - The more carriers connected, the less manual work

4. Reporting & Analytics - Operational dashboards - Financial performance by customer/lane - Custom report builder - Export capability for analysis

Tier 3: Nice-to-Have Features

Valuable but not essential for all operations:

1. Warehouse Management - Container devanning - Inventory tracking - Put-away and pick optimization - Only critical if you operate warehouse facilities

2. AI/Automation - Document OCR (reading PDFs automatically) - Predictive analytics - Automated data entry - Emerging capabilities; evaluate actual value vs. marketing

3. Mobile App - On-the-go access - Notification management - Useful but not critical for most desk-based operations

Feature Evaluation Framework

“ROI isn’t just monetary. If a solution saves time, money, and energy, it’s invaluable.” — Kanav Bhalla, Owner, Transmodal Group

Evaluating Total Cost of Ownership

TMS pricing is notoriously opaque. Here’s how to understand what you’ll actually pay.

Pricing Models Explained

Per-User Licensing - Pay for each person using the system - Common in mid-market TMS - Watch for: User tier limitations (admin vs. standard)

Per-Shipment/Transaction - Pay based on shipment volume - Common in enterprise TMS - Watch for: Costs scale with growth (good problem, but plan for it)

Module-Based - Base system plus add-on modules - Watch for: Core features hidden in “optional” modules

All-Inclusive - Flat per-user fee with all features included - Simplest to budget - Example: GoFreight’s approach

The Hidden Costs

Implementation Fees - Enterprise TMS: $25,000-$100,000+ - Mid-market TMS: $0-$10,000 (often included) - Question to ask: “What’s included in implementation?”

Training Costs - Enterprise TMS: Weeks of formal training, often paid - Mid-market TMS: Days to become productive - Hidden cost: Lost productivity during learning curve

“Training is a nightmare” — Common CargoWise user complaint

Integration Charges - Per-connection fees for carrier integrations - Custom API development costs - Question to ask: “Which integrations are included?”

Support Tiers - Basic support included, premium costs extra - Response time SLAs - Dedicated CSM availability

Ongoing Customization - Configuration changes post-go-live - Report customization - Workflow modifications

TCO Comparison Example

Questions to Ask Every Vendor

1. “What’s included in the subscription price?”
2. “What are implementation costs and timeline?”
3. “Which integrations are included vs. extra?”
4. “What does support look like, and is it included?”
5. “Are there transaction or volume-based fees?”
6. “What happens if we add users?”
7. “What does contract renewal typically look like?”

“We’re paying too much for what we use” — Common enterprise TMS complaint

The Vendor Evaluation Process

A structured evaluation prevents expensive mistakes. Here’s a proven process.

Step 1: Document Requirements (Before Looking at Demos)

Current State Assessment: - What systems do you use today? - What’s working vs. broken? - How many shipments/month? - How many users need access?

Must-Have vs. Nice-to-Have: - List absolute requirements (deal-breakers if missing) - List desired features (influence decision but not critical) - Be honest—everything can’t be must-have

Integration Requirements: - QuickBooks/accounting system - Specific carriers - Customs systems - Other tools in your stack

Step 2: Create a Shortlist

Research Phase: - Industry peers: What do similar companies use? - G2/Capterra reviews: Filter for your company size - Industry associations: Recommendations from peers

Initial Screening: - Does this TMS target companies like mine? - Is pricing in my range? - Do they have customers in my segment?

Shortlist Target: 3-5 vendors for detailed evaluation

Step 3: Structured Demos

Before the Demo: - Share your requirements document - Prepare specific scenarios to see - Involve actual users (not just decision-makers)

During the Demo: - Use YOUR scenarios, not the vendor’s - Watch for: Data re-entry, clunky workflows, unclear processes - Ask: “Can you show me how X works?”

Key Workflows to See: 1. Quote → Booking → Shipment creation 2. Tracking and milestone updates 3. Document generation 4. Invoice creation and accounting sync 5. Reporting and dashboards

Step 4: Reference Checks

Ask the Vendor: - “Can you connect me with 2-3 customers similar to my company?” - Look for: Similar size, similar modes, similar geography

Questions for References: - How was implementation? - How long until your team was productive? - What would you do differently? - How is support when issues arise? - Would you choose them again?

Step 5: Trial or Pilot (If Available)

• Test with real data if possible
• Involve actual users
• Evaluate: Ease of use, speed, workflow fit

Step 6: Negotiation & Contract Review

Negotiate: - Implementation timeline guarantees - Support SLAs - Pricing for growth (user additions) - Contract length flexibility

Contract Review: - Data ownership and portability - Termination terms - Auto-renewal clauses - Price increase limitations

→ Ready to compare platforms? See Best TMS Software 2026 for our recommendations.

Implementation Planning

Successful TMS implementation depends more on preparation than software selection.

Timeline Expectations

Pre-Implementation Checklist

Data Preparation: - Customer/partner records cleanup - Rate agreement organization - Historical shipment data (what needs to migrate?) - User list with roles/permissions

Process Documentation: - Current workflows (how things work today) - Desired workflows (what should change) - Exception handling procedures

Team Preparation: - Identify project owner (internal champion) - Select super-users for advanced training - Schedule training windows - Communicate timeline to team

Implementation Phases

Phase 1: Configuration (Week 1-2) - System setup for your workflow - User accounts and permissions - Integration configuration

Phase 2: Data Migration (Week 2-4) - Customer/vendor import - Rate agreements - Open shipment migration (if needed)

Phase 3: Training (Week 3-5) - Role-based training sessions - Hands-on practice in sandbox - Documentation and quick reference guides

Phase 4: Go-Live (Week 5-8) - Parallel running option - Live support availability - Issue triage and resolution

“Onboarding was simple, and the platform is easy to use.” — Dipty Jardosh, Operations Director, GC Logistics

Success Factors

What leads to smooth implementation: - Clean data going in - Engaged internal champion - Staff involvement in training - Realistic timeline expectations - Strong vendor support

What causes problems: - Scope creep during project - Key people unavailable for training - Dirty data requiring extensive cleanup - Trying to replicate every old workflow - Go-live during busy season

Red Flags and Warning Signs

During your evaluation, watch for these warning signs.

Pricing Red Flags

• “It depends” without ranges: Legitimate vendors can provide ballpark pricing
• Excessive module add-ons: Core features shouldn’t require premium upgrades
• Unclear implementation costs: Get it in writing before signing

Demo Red Flags

• Canned demo only: Won’t show your specific workflows
• “That’s a roadmap item”: Features promised but not delivered
• Can’t provide references: No customers willing to speak

Implementation Red Flags

• 6+ month timeline for mid-market company: Unnecessarily complex
• No dedicated implementation support: You’re on your own
• Extensive customization required: Base product doesn’t fit

Support Red Flags

• Ticket-based only: No direct access to support team
• Slow response guarantees: Days vs. hours
• Premium support required: Basic support inadequate

Contract Red Flags

• Long lock-in (3+ years): Limited flexibility
• Auto-renewal without notice: Traps you in
• Data hostage: Difficult or expensive to export your data

“CargoWise support is useless when we need help fast” — Feedback from CargoWise evaluators

Trust Your Gut

If something feels off during evaluation: - The demo seems rehearsed and avoids your questions - References sound scripted - Sales pressure intensifies near deadline - Pricing changes significantly from initial conversation

…those instincts are usually right.

FAQs: TMS Software Buying Guide

What is the best TMS software for freight forwarders? The best TMS depends on your company size and needs. For mid-market forwarders (10-100 employees), look for purpose-built forwarding software with strong accounting integration and reasonable implementation timelines. Enterprise solutions like CargoWise serve global companies but come with complexity and cost that may not fit smaller operations.

How much does TMS software cost? TMS pricing varies by tier: - SMB solutions: $50-150/user/month - Mid-market: $100-400/user/month - Enterprise: $500-2,000+/user/month Total cost includes implementation, training, integrations, and support. Get all-in pricing before committing.

What’s the difference between TMS and ERP? TMS (Transportation Management System) focuses specifically on freight and logistics operations. ERP (Enterprise Resource Planning) covers all business functions including HR, procurement, and finance. Most forwarders use TMS integrated with accounting software rather than full ERP.

How long does TMS implementation take? Enterprise TMS: 6-12+ months Mid-market TMS: 4-8 weeks Basic TMS: 1-2 weeks Timeline depends on data complexity, integrations, and customization requirements.

Should I choose cloud or on-premise TMS? Cloud TMS is standard in 2026. Benefits include: accessible from anywhere, automatic updates, no server maintenance, faster implementation. On-premise only makes sense for specific security requirements (rare in freight forwarding).

What questions should I ask TMS vendors? Key questions: 1. What’s included vs. extra cost? 2. What does implementation look like? 3. Can I speak with customers my size? 4. What’s your support model? 5. What are contract terms?

Conclusion

Choosing TMS software isn’t about finding the system with the most features—it’s about finding the right fit for your specific operation, team, and growth trajectory.

For most growing freight forwarders, the winning formula is: - Purpose-built for forwarding (not shipper-focused TMS) - Right-sized for your company (not enterprise complexity) - Fast implementation (weeks, not months) - Strong accounting integration (especially QuickBooks) - Responsive support when you need help

“GoFreight is very user friendly, and I am quick in the system… I tried 7 different systems before.” — Janko Wille, CEO, Allround Forwarding Midwest

The best TMS becomes invisible—it just works, letting your team focus on customers instead of fighting software.

Ready to evaluate your options? - Start with requirements documentation - Create a shortlist of 3-5 purpose-built forwarding TMS platforms - Run structured demos with your actual workflows - Check references from similar companies - Make a decision based on fit, not just features

Ready to see if GoFreight fits your operation? Request a GoFreight Demo →

Related Content

• What is TMS? — TMS fundamentals
• Best TMS Software 2026 — Platform comparison
• Best TMS for Small Business — SMB-focused options
• GoFreight vs CargoWise — Enterprise comparison
• Best Freight Management Software — FMS options

Published: January 2026 Source: GoFreight Master ICP, Customer Success Stories