Keelway vs Tai Software
Keelway lives in Gmail. Tai lives in the TMS.
Tai Software is a modern broker TMS with AI features baked inside the TMS workflow. Keelway is an AI carrier-email triage layer that lives in Gmail. They're not the same shape and they don't replace each other. Honest head-to-head — and why "Tai + Keelway" is a real configuration for brokerages that want both.
Where the broker actually works
The honest tiebreaker between Tai's bundled AI and Keelway's focused AI is "where does the broker live all day?"
- Brokers in the TMS — quote workflows, carrier dashboards, document handling. Tai's native AI covers a lot of this surface.
- Brokers in Gmail — reading inbound replies, comparing rates, deciding who to call back. Tai's AI doesn't reach this surface; Keelway is built for it.
Most brokerages we talk to honestly admit their team spends more time in Gmail than they'd like. That's the surface where Keelway wins.
Side by side
| Feature | Keelway | Tai Software |
|---|---|---|
| Category | AI carrier-email triage layer | Modern broker TMS with bundled AI |
| Where it operates | Gmail | Tai web app |
| Pricing — published | $799/mo flat (everything included) | $995–$7,925/mo by tier |
| Inbound carrier-reply ranking | Core product | Partial — TMS-side carrier dashboard |
| Per-reply FMCSA trust score | Yes — per-reply, refreshed at scoring time | Carrier-level, not per-reply |
| Per-reply rate extraction | Yes — every reply, every format | Limited |
| Load lifecycle management | Out of scope | Native |
| Accounting / settlements | Out of scope | Native |
| Implementation timeline | Under 2 weeks | 4–8 weeks typical |
| TMS replacement | No — runs on top | Yes — replaces legacy TMS |
| Run alongside | Yes — Tai + Keelway is real config | Yes |
| Best for | Brokerages keeping their TMS, fixing the inbox | Brokerages replacing legacy TMS with modern UX |
The Tai + Keelway combined stack
For brokerages that want both layers — Tai's modern TMS and Keelway's inbox AI — the configuration is straightforward:
- Tai — load lifecycle, quote workflows, accounting, document handling, AI features inside the TMS UI.
- Keelway — inbox triage, per-reply trust scoring, rate extraction. Booked carrier writes back to Tai via API.
Both prices are published — Tai by tier, Keelway at $799/mo flat (AI carrier-email triage included). Total stack cost is predictable and doesn't balloon with per-seat licenses.
Frequently asked questions
Are Keelway and Tai the same kind of product?+
No. Tai Software is a modern broker TMS — load lifecycle, accounting, document automation, with bundled AI features inside the TMS surface. Keelway is an AI inbox layer — Gmail-native carrier reply triage that runs above any TMS. Different categories. They actually pair well together; many Tai customers run Keelway on top.
Doesn't Tai already have AI? Why add Keelway?+
Tai's AI is bundled into the TMS workflow — it lives where Tai's UI is. Keelway lives in Gmail, where carrier replies actually land. The decision is mostly about where your brokers spend their day. If they live in Tai, Tai's AI may be enough. If they live in Gmail reading carrier replies, Keelway is the more direct fix. Some brokerages run both — Tai's TMS-side AI for ops workflows and Keelway's inbox-side AI for the email layer.
How does pricing compare directly?+
Tai publishes tiered pricing — entry around $995/month (2 staff, 200 shipments), Pro up to roughly $7,925/month (25 staff, 2,500 shipments). AI features are bundled at the higher tiers. Keelway is $799/mo flat, every feature included, 30-day free trial. For a brokerage doing 500 loads/month: Tai mid-tier might be $3,000–$5,000/month for the full TMS, Keelway is $799/mo flat (AI carrier-email triage included). Different jobs at different price points.
If I'm choosing my single broker tool, do I pick Tai or Keelway?+
Tai. You can't run a brokerage without a TMS. You can run one without inbox AI (just slower). The honest framing: Tai is mandatory if your TMS choice is Tai; Keelway is mandatory once your inbound carrier email volume is high enough that brokers are losing real time to triage. The two decisions are independent.
Can Keelway integrate with Tai?+
Yes. Dedicated integration page exists. Keelway writes booked carriers and trust scores back to Tai via API. Your Tai workflow doesn't change; brokers get an AI-ranked carrier list inside Gmail.
Will Tai eventually ship Keelway-style inbox AI as part of the TMS?+
Possibly — they've signaled an AI focus. Even if they do, two things matter: (1) Inbox-native UX is hard to ship from inside a TMS surface; brokers don't want to leave Gmail. (2) Trust scoring depth requires the FMCSA-and-email-domain pipeline Keelway has built specifically. Bundled features rarely outperform focused tools on the focused job.
What's the strongest stack — Tai alone, Tai + Keelway, or Keelway + a different TMS?+
By size: $1M–$10M brokerage with Tai already → Tai + Keelway is incremental value, low risk. New brokerage looking at TMS choice → Tai is a credible TMS pick; add Keelway from day one for the inbox layer. SMB shop on AscendTMS or Aljex → don't migrate to Tai just for AI; add Keelway above your current TMS, save the migration cost.
Tai for the TMS. Keelway for the inbox.