FreightFlow360 vs Fleetworks

Different products. Different segments.

Fleetworks raised $17M to serve the 150 brokerages above $100M in gross revenue. We are built for the 17,000 sub-50 shops priced out of that tier.

This page exists so you can pick the right tool for your size. We are not trying to win every deal. We are trying to win the deals we are built for.

[YC W24: Fleetworks, accessed Oct 2025][fleetworks.com, accessed Oct 2025]

Segmentation: who each product is for

The clearest difference is not features. It is target customer.

Dimension	Fleetworks (enterprise) [YC profile, accessed Oct 2025]	FreightFlow360 (SMB)
Brokerage size	Top-150 brokers, $100M+ gross revenue	Sub-50 headcount, 50 to 500 loads per month
Implementation	Dedicated project team, multi-month rollouts	Connect Gmail, ship in 5 minutes, no IT
Procurement	RFP, SOC 2 packet, security review, custom MSA	Self-serve signup, monthly billing
Pricing model	Custom pricing, annual contracts, per-seat fees	Published flat tiers, monthly, no per-seat fees
Integration depth	Custom enterprise stacks, in-house TMS extensions	AscendTMS, McLeod, Gmail-first, no rip-and-replace

Pricing transparency

Enterprise AI freight ops tools quote on request. We publish.

Fleetworks

Custom pricing

Pricing is provided through sales conversations. Annual contracts and per-seat structures are typical for the enterprise AI freight ops category Fleetworks targets.

[fleetworks.com, accessed Oct 2025]

FreightFlow360

Published. Monthly. Flat.

$299/mo Starter, 300 loads
$749/mo Pro, 1,500 loads
$1,999/mo Scale, 5,000 loads
No per-seat fees. No annual lock-in. Cancel anytime.

Integration depth

We sequence by where SMB brokers actually live. AscendTMS first. McLeod next. TMW after.

Priority 01

AscendTMS

Most common SMB TMS for sub-50 brokerages. Email-first ingestion already works on top of it today.

Priority 02

McLeod

The next-most-common SMB TMS in our target segment. On the integration roadmap.

Priority 03

TMW

Enterprise-tilted, lower density in our segment. Supported through email-first ingestion in the meantime.

Multi-stop rate con parsing

Multi-stop rate cons are where naive parsers break. Order numbers, stop sequencing, appointment windows, and hand-off references stop reading like a single load and start reading like a routing graph.

Our parser was stress-tested against an 8-stop rate con (Order #760902 from a real Gulick rate confirmation pattern). The parser correctly emitted 8 stops with sequenced pickup and drop-off pairs, lane-level consignee data, and per-stop appointment windows.

We do not publish the parser internals. The point is operational: if your shippers send 4-stop, 6-stop, or 8-stop rate cons, FreightFlow360 ingests them on day one without manual rekeying.

Side-by-side, line by line

Feature	Fleetworks [fleetworks.com, accessed Oct 2025]	FreightFlow360
Published pricing	Custom pricing, contact sales	Starter $299, Pro $749, Scale $1,999, all monthly
Annual contract required	Typical for enterprise AI freight ops tools	No. Cancel anytime, monthly billing
Per-seat fees	Common in enterprise AI freight ops contracts	Zero per-seat fees on every paid tier
Free tier	Not advertised	Yes, 25 loads per month, all core features
Target customer	Top-150 brokers and large 3PLs	Sub-50 headcount brokers, 50 to 500 loads per month
AscendTMS-first integration	Enterprise stacks (TMW, McLeod) emphasized	AscendTMS-first, then McLeod, then TMW
Onboarding time	Dedicated implementation engagement	5 minutes, email-first, no IT
Email-first ingestion	Not the primary onboarding path	Primary onboarding path, works on top of any TMS
N-stop rate con parsing	Not publicly documented	Stress-tested on multi-stop rate cons up to 8 stops

When Fleetworks is the right call

→You run a top-150 brokerage with $100M-plus in gross revenue.
→You have a dedicated implementation team and a six-figure annual budget for AI freight ops automation.
→Your stack is custom enterprise (TMW or in-house TMS) and you need deep, bespoke integration work.
→RFP, SOC 2 review, and annual MSA are part of how your procurement team buys software.

If three of those four describe you, talk to Fleetworks. They are built for that profile.

When FreightFlow360 is the right call

→You run a sub-50 headcount brokerage doing 50 to 500 loads per month.
→You are on AscendTMS, McLeod, or running Gmail and a spreadsheet.
→You buy on flat-rate procurement, not RFPs. Monthly billing matters more than annual discount math.
→Founder-led ops. The owner is in the dispatch group chat at 6am.

Start free

Common questions

Is FreightFlow360 a Fleetworks competitor?

In feature category, yes. In market segment, no. Fleetworks targets the 150 brokers with $100M-plus gross revenue. We target the 17,000 sub-50 shops priced out of that tier. Most prospects we see are not the same prospects they see.

Why publish a comparison page if we are not competing for the same deals?

Buyers compare. When a sub-50 broker reads about an enterprise AI freight ops tool, they need a clear answer on whether the tool is built for them. We would rather give that answer ourselves than have a third-party affiliate site invent it.

When should I pick Fleetworks instead?

If you run a top-150 brokerage with a dedicated implementation team, custom enterprise stack integrations, and a six-figure annual budget for ops automation, Fleetworks is built for you. Read the "When Fleetworks is the right call" section below.

How current are these claims?

Every Fleetworks claim on this page links to their own site or YC profile with the access date. If you find a stale or incorrect citation, email hello@freightflow360.com and we will fix it within 24 hours.

Sources

Fleetworks is an independent product. All trademarks belong to their respective owners. FreightFlow360 has no affiliation with Fleetworks. If a citation appears stale or incorrect, email hello@freightflow360.com.