A comprehensive framework for evaluating any freight management system. Use this before your next software decision.
Introduction
Choosing a Transportation Management System (TMS) or freight forwarding software is one of the most consequential decisions a forwarder makes. The right choice accelerates growth and efficiency. The wrong choice creates years of frustration, hidden costs, and operational friction.
Yet most forwarders approach this decision without a systematic framework. They watch demos, nod along, and hope they're asking the right questions.
This checklist changes that approach. Use it to evaluate any freight management system: your current platform, alternatives you're considering, or vendors pitching you.
How to Use This Checklist
Scoring System:
0 = No / Poor / Not Available
1 = Partial / Adequate / With Limitations
2 = Yes / Excellent / Fully Meets Needs
Process:
Complete this checklist for your current system first (baseline)
Complete it for each alternative during evaluation
Compare scores across categories
Investigate any category where you score below 50%
Category 1: Pricing & Cost Transparency (20 points)
Understanding the true cost requires asking the right questions.
| # | Question | Score (0-2) |
|---|---|---|
| 1.1 | Is pricing published on their website? | |
| 1.2 | Can you get a detailed quote without a lengthy sales process? | |
| 1.3 | Is pricing per-user (predictable) rather than per-transaction (variable)? | |
| 1.4 | Are all core features included in the base price? | |
| 1.5 | Is ISF/AMS filing included (not an extra fee)? | |
| 1.6 | Is training included in the price? | |
| 1.7 | Is customer support included (not tiered)? | |
| 1.8 | Can they provide 3-year price increase history? | |
| 1.9 | Are price locks or caps available? | |
| 1.10 | Are contract exit terms reasonable? |
Category 1 Total: ___ / 20
Red Flags:
"Contact sales for pricing"
Per-transaction fees that scale with success
Tiered support with basic tier being inadequate
History of significant price increases
Category 2: Core Operations Functionality (24 points)
Does the system handle your actual day-to-day workflows?
| # | Question | Score (0-2) |
|---|---|---|
| 2.1 | Does it support your primary transport modes? (Ocean, Air, Trucking) | |
| 2.2 | Can you manage ocean FCL shipments end-to-end? | |
| 2.3 | Can you manage ocean LCL/consolidation? | |
| 2.4 | Can you manage air freight workflows? | |
| 2.5 | Is domestic trucking/drayage integrated? | |
| 2.6 | Can you save incomplete entries and return later? | |
| 2.7 | Does the workflow match how your team actually operates? | |
| 2.8 | Are batch operations available for bulk updates? | |
| 2.9 | Is multi-office/multi-branch supported? | |
| 2.10 | Is multi-currency fully supported? | |
| 2.11 | Can you customize workflows without developer help? | |
| 2.12 | Is the search function fast and flexible? |
Category 2 Total: ___ / 24
Key Insight:
"You can't proceed even if you make a small mistake." — Operations manager describing rigid workflow limitations
If workflows don't match your operation, you'll fight the system daily.
Category 3: Compliance & Filing (20 points)
Compliance is non-negotiable. How well does the system support it?
| # | Question | Score (0-2) |
|---|---|---|
| 3.1 | Is ISF filing integrated (not third-party)? | |
| 3.2 | Is AMS filing integrated? | |
| 3.3 | Is AES filing available for exports? | |
| 3.4 | Can you see filing status on the shipment record? | |
| 3.5 | What's the per-filing cost? (2=included, 1=reasonable, 0=expensive) | |
| 3.6 | Are automated filing reminders available? | |
| 3.7 | Does the system validate data before submission? | |
| 3.8 | Can customers see filing status in their portal? | |
| 3.9 | Is there an audit trail for compliance documentation? | |
| 3.10 | Are regional compliance requirements supported? (e.g., e-invoicing) |
Category 3 Total: ___ / 20
Key Insight:
"We didn't use [the system] to do this because it's too expensive. They use another third party." — Branch manager on ISF/AMS filing
Third-party filing means double-entry and fragmented visibility.
Category 4: Visibility & Task Management (20 points)
Can you see what's happening across your operation?
| # | Question | Score (0-2) |
|---|---|---|
| 4.1 | Is there a centralized task management dashboard? | |
| 4.2 | Can managers see team workload and assignments? | |
| 4.3 | Are overdue tasks highlighted automatically? | |
| 4.4 | Can you set automated alerts for key milestones? | |
| 4.5 | Are exception notifications configurable? | |
| 4.6 | Can you see all pending items across all shipments? | |
| 4.7 | Is there a daily/weekly summary view? | |
| 4.8 | Can you filter and search shipments easily? | |
| 4.9 | Are custom reports available without IT help? | |
| 4.10 | Can reports be scheduled and auto-delivered? |
Category 4 Total: ___ / 20
Key Insight:
"I can only see it being added... but I can't see if it's done." — Operations manager on task visibility
If you're tracking tasks via email, you're losing visibility.
Category 5: Customer Experience (16 points)
How do your customers interact with your operation through this system?
| # | Question | Score (0-2) |
|---|---|---|
| 5.1 | Is there a customer-facing portal? | |
| 5.2 | Can customers track shipments in real-time? | |
| 5.3 | Can customers access and download documents? | |
| 5.4 | Can the portal be branded with your identity? | |
| 5.5 | Can customers submit booking requests online? | |
| 5.6 | Are automated status notifications available? | |
| 5.7 | Can notification preferences be customized? | |
| 5.8 | Is mobile access available for customers? |
Category 5 Total: ___ / 16
Your software reflects on your service. A poor portal means more phone calls and emails.
Category 6: Accounting & Finance (20 points)
Is financial management integrated or fragmented?
| # | Question | Score (0-2) |
|---|---|---|
| 6.1 | Is accounting built-in (not requiring separate software)? | |
| 6.2 | Can you generate invoices directly from shipment data? | |
| 6.3 | Is accounts receivable management integrated? | |
| 6.4 | Is accounts payable management integrated? | |
| 6.5 | Can you see profit/loss by shipment? | |
| 6.6 | Are agent settlements handled in-system? | |
| 6.7 | Is QuickBooks/accounting software integration available? | |
| 6.8 | Is multi-currency properly supported with exchange handling? | |
| 6.9 | Can you batch process invoices? | |
| 6.10 | Are financial reports and aging reports available? |
Category 6 Total: ___ / 20
Built-in accounting = one source of truth. Separate systems = reconciliation headaches.
Category 7: Support & Training (20 points)
Will you have a partner or a ticket queue?
| # | Question | Score (0-2) |
|---|---|---|
| 7.1 | Will you have a dedicated success manager? | |
| 7.2 | Or is support ticket-based only? (2=dedicated, 0=ticket only) | |
| 7.3 | What's the average support response time? (2=<4hrs, 1=<24hrs, 0=>24hrs) | |
| 7.4 | Is support available in your primary time zone? | |
| 7.5 | Is phone support available (not just email)? | |
| 7.6 | Is initial training included in the price? | |
| 7.7 | Is ongoing training available at no extra cost? | |
| 7.8 | Are training resources available on-demand (videos, docs)? | |
| 7.9 | How long does it typically take to train new users? (2=<2wks, 1=<1mo, 0=>1mo) | |
| 7.10 | Is certification required to use the system? (2=no, 1=optional, 0=required) |
Category 7 Total: ___ / 20
Key Insight:
"Every customer gets a dedicated onboarding success manager. Not a ticket queue—a person."
The difference between dedicated support and ticket queues is transformational.
Category 8: Implementation & Migration (16 points)
How quickly and safely can you get up and running?
| # | Question | Score (0-2) |
|---|---|---|
| 8.1 | What's the typical implementation timeline? (2=<4wks, 1=<3mo, 0=>3mo) | |
| 8.2 | Is parallel running supported during transition? | |
| 8.3 | Is data migration assistance provided? | |
| 8.4 | What data formats can be imported? | |
| 8.5 | Is phased rollout available for multi-office? | |
| 8.6 | Is implementation included in price or extra cost? | |
| 8.7 | Who manages the implementation project? (2=dedicated PM, 0=self-service) | |
| 8.8 | What happens if the timeline slips? |
Category 8 Total: ___ / 16
Category 9: Integration & Connectivity (16 points)
Does the system connect to your ecosystem?
| # | Question | Score (0-2) |
|---|---|---|
| 9.1 | How many carrier EDI connections are pre-built? | |
| 9.2 | Are major ocean carriers integrated? | |
| 9.3 | Is container tracking automated? | |
| 9.4 | Are customs broker connections available? | |
| 9.5 | Is there an open API for custom integrations? | |
| 9.6 | Can you connect to customer systems (EDI/API)? | |
| 9.7 | Are pre-built integrations available for common tools? | |
| 9.8 | What does custom integration typically cost? |
Category 9 Total: ___ / 16
Category 10: Platform & Technology (20 points)
Is this modern software or legacy technology?
| # | Question | Score (0-2) |
|---|---|---|
| 10.1 | Is the system fully cloud-based (no installation)? | |
| 10.2 | Can you access from any browser? | |
| 10.3 | Is mobile access available? | |
| 10.4 | How often are updates released? (2=continuous, 1=quarterly, 0=annually) | |
| 10.5 | Are updates automatic (no manual upgrades)? | |
| 10.6 | What's the uptime SLA? (2=>99.9%, 1=>99%, 0=no SLA) | |
| 10.7 | Where is data hosted? (security/compliance) | |
| 10.8 | What security certifications are in place? | |
| 10.9 | Is there a disaster recovery plan? | |
| 10.10 | What's the data backup frequency? |
Category 10 Total: ___ / 20
Scoring Summary
Transfer your category totals:
| Category | Max | Score | % |
|---|---|---|---|
| 1. Pricing & Transparency | 20 | ||
| 2. Core Operations | 24 | ||
| 3. Compliance & Filing | 20 | ||
| 4. Visibility & Task Mgmt | 20 | ||
| 5. Customer Experience | 16 | ||
| 6. Accounting & Finance | 20 | ||
| 7. Support & Training | 20 | ||
| 8. Implementation | 16 | ||
| 9. Integration | 16 | ||
| 10. Platform & Technology | 20 | ||
| TOTAL | 192 |
Interpretation:
| Score | Assessment |
|---|---|
| 160-192 (83%+) | Excellent fit |
| 130-159 (68-82%) | Good fit with minor gaps |
| 100-129 (52-67%) | Acceptable with significant gaps |
| <100 (<52%) | Poor fit—look elsewhere |
Reference Questions for Vendors
Ask these during demos and reference calls:
"What's your implementation timeline for a company our size?"
"What surprised customers after going live (good and bad)?"
"How responsive is support when we have issues?"
"What's your price increase history over the past 3 years?"
"Can we speak with a customer who switched from our current system?"
"What do customers say is missing or needs improvement?"
Download This Checklist
Want a printable PDF version?
Use it in vendor meetings, share with your evaluation team, and keep a record of your analysis.
Related Resources:
Learn more about our freight forwarding software or schedule a demo →.
Last updated: December 2025
