# Roadmark vs PortPro: a side-by-side drayage TMS comparison

> PortPro is a drayage-specialist TMS; Roadmark runs drayage in one system with trucking, brokerage and every other mode, with AI agents that draft the work.

URL: https://roadmark.ai/compare/portpro
Language: en
Last updated: 2026-10-01

**TL;DR:** PortPro is a drayage operating platform for drayage carriers and brokers: it pulls container status, holds and last free day from terminal websites, and books terminal appointments automatically in the US port markets it lists. Roadmark runs drayage (appointments, the free-time clock, chassis, street turns, pre-pulls and yard storage) in the same system as over-the-road trucking, brokerage, every other mode and several companies, with AI agents that draft the work for a person to approve. For a carrier that only does port drayage, a specialist may fit better.

*Last reviewed October 1, 2026*

## Roadmark and PortPro, row by row.

Each cell says what the product does, not only whether it does it. The sources are listed at the foot of the page.

|  | PortPro | Roadmark |
| --- | --- | --- |
| What it is | A drayage operating platform for drayage carriers, drayage brokers and companies that do both, from delivery order to payment. | A TMS for asset carriers, freight brokers and groups of companies, with every mode on one load record and AI agents drafting the routine work. |
| Terminal appointments | **Yes.** Books terminal appointments automatically from preferences you set, and can book the empty return when a container is marked empty. Live in NY/NJ, LA/Long Beach, Oakland, Seattle/Tacoma, Virginia and Savannah as of September 2025. | **Yes.** Books the terminal appointment from the load, or tracks one already booked; the Tracking agent drafts the pickup for a dispatcher to approve. |
| Container status from the terminal | **Yes.** Pulls up to 13 data points per container from the terminal website, including container status, customs, freight and broker holds, last free day and vessel ETA. | **Yes.** Availability, holds, last free day, fees and the pickup appointment time come automatically from the terminals and rail ramps through Terminal49, onto each container's load, where the free-time clock counts down. |
| Free time: demurrage and per diem | **Yes.** Last free day from the terminal, with alerts as it nears; a per diem dashboard of loads that have or are projected to have per diem, with backup for disputes and empty-return locations by steamship line. | **Yes.** Counts down every container's last free day and shows what demurrage and per diem have cost so far, and will cost by a given date if nothing moves. |
| Chassis | **Partial.** Says it handles chassis management: finds an available chassis to assign to the driver and reports chassis utilization; chassis split is a driver-pay item, and its AI flags missed charges such as chassis rentals. Chassis pools and chassis per diem billing aren't described; ask. | **Yes.** Assigns chassis from your pools, records splits, and tracks chassis per diem for each day a chassis is under a box, billed on the invoice. |
| Street turns | **Yes.** Street turns planned in the TMS, including pre-planned without a driver, with the linked export load shown. | **Yes.** Proposes the street turn when an import empties near an exporter who needs the same box, once the ocean carrier approves. |
| Pre-pulls and yard storage | **Partial.** Pre-pull is a driver-pay item alongside chassis split, waiting time and overweight. Yard storage billing isn't described; ask. | **Yes.** Pre-pulls and drops to your own yard, with the yard days counted on the load and billed as storage. |
| Drayage billing | **Yes.** Invoices in hours with customer rates applied automatically; its AI biller flags accessorials, checks documents such as PODs and TIRs, and pushes data to customer portals. | **Yes.** Accessorials billed at the terminal's own rate, with demurrage passed through at cost; the Billing agent drafts the invoice for approval. |
| Other modes | **—.** Built for drayage; it says it fits companies doing 40% or more drayage. Other modes aren't described; ask. | **Yes.** Truckload through LTL, drayage, intermodal, rail, air and ocean, on one record. |
| Trucking and brokerage together | **Yes.** A carrier-and-broker product: move your own loads and broker others out to drayage carriers, with carrier invoices accepted or rejected in the TMS. | **Yes.** Your own trucks and brokered loads in one system, with carriers vetted at onboarding and loads posted to DAT, Truckstop and other load boards. |
| Several companies | **—.** Not described; ask. | **Yes.** Multiple companies and divisions in one platform, with separate records, internal rates and access controls. |
| AI agents | **Yes.** Jerry, an AI dispatcher, builds and re-plans the schedule and assigns drivers; Helen, an AI biller and CSR, applies billing rules, checks documents, flags accessorials and answers quote requests. Its site says your team reviews and approves invoices, and that PortPro's team builds the AI workflows around your process; whether a person approves each dispatch change isn't described. | **Yes.** Seven agents, one per job, draft quotes, plans, appointments, tracking updates and invoices, with the numbers and rule shown, for a person to approve. |
| Works in your AI assistant | **—.** Not described; ask. No MCP or assistant connector named on PortPro's site (checked October 2026). | **Yes.** Claude, ChatGPT, Gemini and Copilot, through MCP. |
| Integrations | Customer EDI and API, location from drivers' phones or your ELD provider, and TIRs and EIRs pulled from terminal websites. Its release notes describe QuickBooks connections, including QuickBooks Desktop through Rutter. | Public API and webhooks in every plan; EDI 204 in, 990, 214 and 210 out; ELDs, load boards and accounting. |
| Deployment | **—.** Web-based. On-premise isn't described; ask. | **Yes.** Confirm hosting regions and deployment options with Roadmark before contracting. |
| Pricing (US dollars) | Not published; its site leads to a demo. Its Profit Driver package is for fleets of 5 to 20 trucks, and it says it fits companies in North America with 5 or more drivers. | Roadmark starts from $499 USD/month with unlimited users. Start with one workflow beside your current TMS and confirm the setup and price with our team. |

## Roadmark is the better choice if

- Drayage is one part of your business: you also run over-the-road trucks, broker freight, or move intermodal, rail, air or ocean, and want every mode on the same load record.
- You run more than one company or division and want them in one system, each with its own books, hauling for each other at an internal rate.
- You want AI agents to draft the routine work, from the pickup appointment to the invoice, for a person on your team to approve, with the numbers and the rule behind each draft shown.
- You want chassis pools, splits and chassis per diem, pre-pulls and storage in your own yard counted on the load and billed, with the terminal's demurrage passed through at cost.
- Your team wants to ask about containers and loads from Claude, ChatGPT, Gemini or Copilot.

## PortPro is the better choice if

- You want terminal and empty-return appointments booked hands-off by slot rules you set, with PortPro rechecking for better times. Ask which of your terminals it covers: its latest public list, from September 2025, names NY/NJ, Los Angeles/Long Beach, Oakland, Seattle/Tacoma, Virginia and Savannah.
- Your business is port drayage and you want software built for nothing else: PortPro describes itself as a drayage operating platform, for companies doing 40% or more drayage.

PortPro and Roadmark both run a drayage operation from the delivery order to the invoice. They differ in how much of the business beyond the port each one is built for, and in where the container data comes from.

PortPro describes itself as a drayage operating platform for drayage carriers, drayage brokers and companies that do both ([portpro.io](https://portpro.io/)). It pulls up to 13 data points per container from terminal websites, including holds and the last free day ([container tracking](https://portpro.io/features/drayage-carrier/container-tracking)), and books terminal appointments automatically by preferences you set in the US port markets it lists ([appointments](https://portpro.io/all-resources/blog/article/automatically-book-appointments)). Its AI comes as two named roles: Jerry dispatches and Helen bills ([PortPro AI](https://portpro.io/ai)). Its home page says it fits North American companies with 5 or more drivers doing 40% or more drayage, and it doesn't publish prices.

Roadmark is a TMS for asset carriers, freight brokers and groups of companies. On [drayage](https://roadmark.ai/drayage) it reads each container's availability, holds and last free day from the terminals and rail ramps through [Terminal49](https://roadmark.ai/integrations/terminal49), books the terminal appointment from the load or tracks one already booked, counts down every container's free time, proposes street turns, assigns chassis from your pools and tracks chassis per diem, handles pre-pulls and storage in your own yard, and bills each at the terminal's own rate. The same load record carries truckload, LTL, intermodal, rail, air and ocean, and AI agents draft the quote, the plan, the appointment, the tracking update and the invoice for someone on your team to approve (see [/ai-agents](https://roadmark.ai/ai-agents)).

## When PortPro is the better choice

In the port markets it lists (NY/NJ, Los Angeles/Long Beach, Oakland, Seattle/Tacoma, Virginia and Savannah as of September 2025), PortPro books terminal and empty-return appointments automatically, by slot rules you set.

## When Roadmark is the better choice

If drayage is one part of a larger operation (your own over-the-road trucks, a brokerage, intermodal, rail, air or ocean), Roadmark keeps it all on one load record, and runs several companies or divisions in one system with separate books and internal rates between them (see [/groups](https://roadmark.ai/groups)). Its agents draft the routine work for a person to approve, with the numbers and the rule behind each draft shown. Chassis per diem and yard storage are counted on the load and billed, your team can ask about loads from Claude, ChatGPT, Gemini or Copilot. Confirm hosting regions and deployment options with Roadmark before contracting.

## What we could confirm, and what we couldn't

Every fact about PortPro here comes from PortPro's own site, blog and release notes, listed under Sources, as of October 1, 2026. We didn't find chassis pools or chassis per diem billing, yard storage billing, modes other than drayage, several companies in one system, an on-premise option or a Claude/ChatGPT/Gemini/Copilot-style assistant connector on its public pages; its help center needs a login, so ask PortPro about any of these. Roadmark's column repeats only what the rest of this site says; see [/integrations](https://roadmark.ai/integrations) for what Roadmark connects to today and [/pricing](https://roadmark.ai/pricing) for how Roadmark is priced.

PortPro is a trademark of its owner. Roadmark is not affiliated with PortPro.

## How we compared

Every comparison on this site is written the same way, so you can check it.

- **Their own words:** Facts about the other product come from its public documentation, pricing and release notes, listed under Sources.
- **What it does, not a score:** Each row says what the product does for a carrier, broker or group, not a number out of ten.
- **Both sides:** Every page also says when the other product is the better choice.
- **Dated and corrected:** The review date moves only when every row has been checked again. If something is out of date, tell us.

## Sources

- [PortPro: drayage software](https://portpro.io/)
- [PortPro: TMS for drayage carriers](https://portpro.io/solutions/drayage-carrier)
- [PortPro: TMS for drayage carriers and brokers](https://portpro.io/solutions/drayage-hybrid)
- [PortPro: drayage broker](https://portpro.io/solutions/drayage-broker)
- [PortPro: PortPro AI](https://portpro.io/ai)
- [PortPro: container tracking](https://portpro.io/features/drayage-carrier/container-tracking)
- [PortPro: terminal appointment booking](https://portpro.io/features/drayage-carrier/book-appointment)
- [PortPro: manually booking appointments? A thing of the past (Sep 11, 2025)](https://portpro.io/all-resources/blog/article/automatically-book-appointments)
- [PortPro: automating empty return appointments (Jul 29, 2025)](https://portpro.io/all-resources/blog/article/automate-empty-return-appointments)
- [PortPro: per diem monitoring](https://portpro.io/features/drayage-carrier/per-diem-monitoring)
- [PortPro: drayage dispatch](https://portpro.io/features/drayage-carrier/dispatch)
- [PortPro: accounts receivable](https://portpro.io/features/drayage-carrier/accounts-receivable)
- [PortPro: driver pay](https://portpro.io/features/drayage-carrier/driver-pay)
- [PortPro: release notes](https://portpro.io/release-notes)
- [PortPro: Profit Tools vs PortPro](https://portpro.io/product-compare/profit-tools-vs-portpro)
- [PortPro: introduces new drayage TMS](https://portpro.io/all-resources/blog/news/portpro-introduces-new-drayage-tms-chain-brain)

## Questions about Roadmark and PortPro

### Is PortPro a direct competitor to Roadmark?

For drayage, yes. PortPro is built only for drayage carriers and brokers. Roadmark runs drayage on the same load record as over-the-road trucking, brokerage and every other mode, across several companies if you have them, with AI agents that draft the work for a person to approve. If port drayage is all you do, a specialist such as PortPro may fit better. See /drayage.

### Does Roadmark pull container availability from the terminals, like PortPro?

Yes. PortPro says it pulls container status, holds, last free day and vessel ETA from terminal websites automatically. Roadmark gets availability, holds, the last free day, fees and vessel and rail milestones automatically from the terminals, shipping lines and railroads through its Terminal49 integration, puts them on each container's load, and books or tracks the terminal appointment from there. Terminal49 publishes which terminals it covers; see /integrations/terminal49.

### Do both handle chassis, pre-pulls and street turns?

Both plan street turns. Roadmark assigns chassis from your pools, records splits and tracks chassis per diem, and counts pre-pulled containers' days in your own yard, billing each on the customer invoice. PortPro says it handles chassis management: it describes assigning an available chassis, reporting chassis utilization, chassis split and pre-pull as driver-pay items, and its AI flagging missed chassis rentals; its public pages don't describe chassis pools, chassis per diem billing or yard storage billing.

### How much does PortPro cost?

Roadmark starts from $499 USD/month with unlimited users. Start with one workflow beside your current TMS and confirm the setup and price with our team. Compare the required workflows, integrations and implementation scope when evaluating other vendors.

### Does PortPro have AI agents like Roadmark's?

PortPro has two named AI roles: Jerry, a dispatcher that plans and re-plans the schedule and assigns drivers, and Helen, a biller and CSR that applies billing rules, checks documents, flags accessorials and answers quote requests. Its site says your team reviews and approves invoices before they go out; it doesn't say whether a person approves each dispatch change. Roadmark's agents draft the quote, the plan, the appointment, the tracking update and the invoice, each showing the numbers and rule behind it, for a person to approve.

## Related pages

- [Drayage](https://roadmark.ai/drayage): Free time, per diem, chassis and port appointments
- [Demurrage and per diem calculator](https://roadmark.ai/tools/demurrage): Last free day, charged days and the total for a container at the terminal or out on per diem, with tiered rates.
- [Demurrage vs per diem vs detention in drayage](https://roadmark.ai/blog/demurrage-per-diem-detention): Who charges demurrage, per diem and detention on a container, when each clock starts and stops, and a worked import example with every charge computed.
- [Intermodal](https://roadmark.ai/intermodal): Ramps and rail cutoffs
- [Terminal49 integration: container availability and holds](https://roadmark.ai/integrations/terminal49): Roadmark reads container availability, holds, last free day, fees, appointments and rail events from Terminal49 onto each drayage and intermodal load.
- [Groups of companies](https://roadmark.ai/groups): Companies, divisions and sister rates

Companies, people and shipment figures in product examples are fictional. They illustrate workflows and are not customer testimonials or measured results.