About SureMile

Built by people who know what a rate con looks like at 11pm.

A third of our team has a CDL. Another third has managed a small fleet. The rest are the kind of engineers who'd rather ride along on a Dallas-to-Chicago run than sit in a sprint review.

01 · Who

Owner-operators and 2–20 truck fleets.

Not mega-carriers. Not brokers. The people who drive the truck and also answer the phone.

02 · Why

The "business" half of driving eats your evening.

Rate cons, BOLs, broker portals, fuel receipts. An hour after every drop, adds up to a full day a week.

03 · How

One app that does the office work while you drive.

Nav, load board, and paperwork share a tab bar. The AI reads documents and proposes loads. You always sign.

The story

Started with a ride-along. Stayed for the problem.

2023

Ride-along #1

Our founder spent 11 days in a sleeper cab with a two-truck owner from Dallas. The driving was the easy part. The "office" work — between drops, at the truck stop, at midnight — was the part that broke people.

2024

First 30 drivers

We built a document parser that could read a rate con without a human. 30 owner-operators volunteered to run it live. The median driver got 4 hours a week back.

2025

One app, not three

Drivers kept switching between our app, Trucker Path, and a broker portal. We folded nav and load search into the same mobile install. That's when it clicked — the "one app" part is the unlock.

2026

220 drivers. 8 states. Still not pretty enough.

We're on 220 trucks across 48 states. The hardest things left are the soft ones: negotiation tone, detention calls, the exact moment to trust autofill vs. double-check. Those are our 2026.

What we won't do

Rules from the drivers, for us.

No "AI-powered" in the hero.

Drivers are skeptical of hype. We'd rather show you what the AI does than tell you it exists. If we can't explain what's automated and what still needs you, we don't ship it.

No stock photos of smiling drivers.

Every quote on this site is a real owner-operator. Names withheld because that's how they wanted it. If we need a picture, it's a truck, not a person.

No surprise pricing page.

You don't negotiate a rate from a pricing table — you negotiate from a phone call. So talk to us. We'll tell you what it costs for your truck count, up front.

No laptop required.

If you need to open a computer to use SureMile, we failed. Everything the driver does has to work from the cab on a phone at a truck stop with one bar.

The team

Fourteen of us. Six with CDLs.

JC
Jesse Carter
Founder · ex O/O
MR
Maria Reyes
Eng lead · fleet ops
DS
Dan Steele
Head of driver
AK
Aisha Khalid
Docs & AI
Join us

If you drive and want to try it — or want to talk to us about your fleet — you know where to find us.

Download the app Book a demo