Notes on technology.

How automation, AI, and purpose-built systems are reshaping lease drafting.

7 entries on file

The Ledger

All Entries

7 entries

§ 01MAR 13, 2026

Technology

Automation vs. AI for Lease Drafting: A Practitioner's Guide

Manual drafting, document automation, and AI generation each make different promises. This guide breaks down what actually works for lease production, and why the distinction between deterministic and probabilistic matters more than any vendor pitch.

LeasePilot Team8 MIN READ

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§ 02FEB 06, 2025

Technology

Why Generic Document Automation Failed CRE Legal Teams

HotDocs and Contract Express have been around for years, yet most CRE teams still draft in Word. The problem: generic tools require CRE teams to build every lease-specific rule from scratch.

David Saltman7 MIN READ

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§ 03DEC 18, 2024

Technology

Supporting Any Complexity in Lease Documents

Most automation tools handle the simple cases and leave 40% or more in Word. We built LeasePilot to push that number significantly lower, custom rent calculations, date-driven logic, dynamic paragraph assembly. Here's how we handle complexity that breaks other systems.

Lior Kedmi9 MIN READ

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§ 04NOV 20, 2024

Technology

AI in Commercial Leasing: What It Can and Can't Replace

AI excels at extraction and pattern recognition. But negotiation strategy, clause selection, and risk assessment require judgment that can't be delegated. Here's where the line is.

David Saltman8 MIN READ

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§ 05SEP 16, 2024

Technology

How We Deconstruct a Lease to Reconstruct It Better

A commercial lease isn't one document, it's five layers mixed together. We decompose them, store them separately, and reconstruct on demand. This architecture is why we can handle complexity that breaks other systems.

Lior Kedmi8 MIN READ

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§ 06JUN 06, 2024

Technology

Why We Chose Automation Over AI Generation, 10 Years Ago, and Still Today

AI generation creates text that needs verification. Automation assembles pre-approved text that doesn't. For legal documents where every word carries liability, the verification burden is the entire game.

Lior Kedmi7 MIN READ

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§ 07MAR 06, 2024

Technology

How LeasePilot Actually Works: A Technical Overview

For technical evaluators doing due diligence: here's how our system actually works. Layered document architecture, deterministic assembly, and the engineering philosophy behind a decade of development.

Lior Kedmi10 MIN READ

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§ What’s next

Reading is one thing. Drafting is another.

See how a custom-built LeasePilot platform fits the way your team actually drafts — your forms, your clauses, your defaults.

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