Searching for route optimization software usually leads to a dozen tabs open, all promising the same things: AI features, cost savings, and a driver app.
But as we head into 2026, feature grids and standard RPF questions don't tell you how a tool performs when your drivers are on the road and things get chaotic.
To find a partner that actually supports your operations, you need to ask harder questions during the demo. Here is what you should ask to ensure the software scales with you rather than holding you back.
1. “How does this handle real-world messiness, not ideal scenarios?”
Many demos run on perfect conditions: five vehicles, twenty stops, and zero traffic. But real-world operations are rarely that predictable.
Ask to see how the software handles:
- Failed delivery attempts that need rescheduling during active routes
- Rush orders arriving after morning optimization is complete
- Driver call-outs that require redistributing stops across remaining vehicles
- Customer time windows that change mid-day
Ideally, the platform should re-optimize automatically when conditions change. If it requires manual dispatcher intervention for every disruption, it defeats the purpose of automation
2. “Who else is using this successfully, and are they similar to us?”
Ask for customers who match your specific use case. Requirements vary dramatically across industries.
Request references from companies with:
- Similar delivery density (dense urban routes versus sprawling suburban areas)
- Comparable order volumes and seasonal fluctuations
- The same operational constraints you face
- Your industry's compliance requirements
For example, cannabis delivery operations need proof of delivery features that meet strict state regulations, including age verification and chain-of-custody documentation. If the vendor can't show you relevant references, you may be helping them figure out your industry.
3. "Is your API documentation public, or is every integration a custom project?"
Public API documentation usually means the platform is designed for easy integration. Some vendors only offer custom-built, hard-coded connections. This approach can create bottlenecks:
- Implementation stretches from weeks to months
- Each integration becomes a separate project with separate costs
- You depend on their development team for every adjustment
- Updates to your other systems can break the connections
Ask to review their API documentation during the demo. If they require an NDA or signed contract first, the integration process will likely be more complex than you’d like.
4. "Will drivers actually use this app?"
Your drivers spend eight hours a day with this app. If the interface is clunky or unreliable, they'll find workarounds that undermine your system.
Check app store reviews before the demo. Look at the rating, read recent feedback, and filter by pain points like battery drain, crashes, or offline performance. This reveals what drivers actually experience daily.
During the demo, ask: "What makes drivers love your app?" Request a week-long trial with your actual drivers before committing.
Driver retention is real. A frustrating app is the difference between a driver who meets their ETA and one who quits.
💡Onfleet’s driver app is rated 4.8 stars by 4,500+ drivers, reflecting an interface teams are comfortable using all day, every day.
5. “How hard is it to switch to this platform?”
If you're currently using route optimization software, it is normal to worry about disrupting operations during a switch. Many companies feel stuck because their current vendor built multiple custom integrations that would be difficult to recreate.
This is why asking about public APIs matters. Custom-built connections can create vendor lock-in. Ask about:
- Typical implementation timelines
- Data migration support
- Whether you can run parallel operations during the switch
- The training format provided
Platforms built on standard APIs generally make switching significantly less disruptive than those requiring custom development work.
6. "Where do teams usually outgrow this platform?"
Every platform has its sweet spot. An honest vendor will be transparent about where theirs ends.
Ask directly:
- At what delivery volume do customers typically need something more robust?
- What operational complexity does the platform struggle with?
- Are there geographical limitations (international operations, certain regions)?
- Which features on the roadmap are still 6-12 months away?
If the vendor claims they handle everything perfectly at any scale, they probably haven't supported enough customers to know their limits yet. The best responses acknowledge trade-offs honestly.
7. “If this isn’t the right fit long-term, how easy is it to move on?”
At Onfleet, we regularly speak with prospects who feel trapped by their current vendor. They want to switch but fear the disruption, the lost data, or the contractual penalties. Vendor lock-in is a real problem that keeps businesses stuck with underperforming software.
Ask upfront:
- Are integrations standard or custom-built? (Custom integrations are hard to replicate elsewhere)
- How you can export your data (full API access or limited CSV downloads?)
- Whether you retain historical route data and analytics after canceling
- Contract terms and early cancellation requirements
Vendors who make it easy to leave are usually confident you'll want to stay. Those who make it deliberately difficult know their retention depends on friction rather than value.
Experience the Route Optimization Software Drivers Actually Love
Thousands of courier teams rely on Onfleet to keep routes running and drivers on track. Our 4.8-star driver app is built for real days on the road, and our open API makes it easy to connect Onfleet to the tools you already use. Start a free trial and see how Onfleet handles the realities of your operation.
🎥 Watch the customer story:
Umer Jamshaid, Senior Director of Operations at The Rounds, explains how Onfleet’s route optimization helped reduce driving times by 17% while completing the same number of tasks.
FAQ on Route Optimization Software:
What is Route Optimization Software?
Route optimization software is a technology solution that calculates efficient routes for delivery vehicles or field teams. It accounts for stops, time windows, traffic, and driver schedules, and adjusts routes in real time as conditions change.
How is AI used in route optimization?
AI analyzes historical delivery data to predict accurate service times, identify traffic patterns, and anticipate customer availability. Machine learning algorithms learn from past routes to improve future optimization, automatically adjust for variables like driver speed, and provide increasingly accurate ETAs. Advanced platforms use AI for dynamic re-routing when disruptions occur.
What key features are essential for route optimization software in 2026?
Essential route optimization software features in 2026 include:
- Real-time dynamic route adjustment
- Intuitive mobile driver apps with offline capability
- Automated customer notifications with accurate ETAs
- Open and well-documented APIs for easy integrations
- Comprehensive analytics on route efficiency and driver performance
- Exception handling workflows for failed deliveries
- Scalability that maintains performance as you grow