By Lawyers, for Lawyers
Deadline Pilot was born out of a simple frustration: calendaring court deadlines is tedious, error-prone, and consumes hours of valuable time that could be spent on substantive legal work. Every litigator knows the drill — a new scheduling order arrives, and someone has to manually read through pages of dates, calculate relative deadlines, and enter each one into the calendar. One missed deadline can mean a malpractice claim. One miscalculated relative date can mean a blown motion cutoff.
We built Deadline Pilot because we lived this problem every day in our own practice. As litigation attorneys, we spent countless hours doing exactly this kind of work — work that is critically important but fundamentally mechanical. We knew there had to be a better way.
Why We Built This
The legal technology market is full of tools designed by engineers who have never set foot in a courtroom. They build products based on assumptions about how lawyers work, not how lawyers actually work. Deadline Pilot is different. Every feature, every workflow, every design decision was made by lawyers who understand the stakes.
We understand that a scheduling order from Palm Beach County reads differently than one from Miami-Dade. We understand that “30 days before trial” doesn't mean 30 calendar days in every jurisdiction. We understand that when an order says “no later than 14 days after the filing of a motion,” your team needs that deadline on the calendar immediately, with the correct date, and sent to everyone who needs to know.
That's why Deadline Pilot doesn't just extract dates — it understands the legal context behind them.
Our Mission
Our mission is to eliminate the mechanical burden of calendaring and e-service processing so that lawyers can focus on what they do best: practicing law. We believe that technology should work for lawyers, not create more work. Deadline Pilot is designed to integrate seamlessly into your existing workflow — upload a document, review the extracted deadlines, and send calendar invitations to your team. That's it.
We are committed to building the most accurate, secure, and easy-to-use deadline extraction and calendaring tool available. We hold ourselves to the same standard of diligence that we expect from our own legal work, because we know what's at stake.
Security First
As lawyers, we understand the sacred obligation of client confidentiality. That is why security is not an afterthought at Deadline Pilot — it is foundational. Every document is encrypted at rest and in transit. Your data is never shared with any third party. You control how long your documents are retained, and you can choose to have them deleted immediately after processing. We built Deadline Pilot the way we would want our own confidential documents handled.
Legal Simplicity
Deadline Pilot is developed by Legal Simplicity, a legal technology company founded by practicing attorneys. We are dedicated to building tools that simplify the practice of law without compromising on quality, security, or the professional standards that define our profession.