Lawyers Who Build: The Future of Legal Tech & AI | Batesly x Clearbrief x Casium

Legal software is having its AI moment, and most of the people deciding what gets built have never billed an hour. This fireside chat is the opposite.

Three lawyers who build legal tech: Rachel Bender (Co-Founder & CEO of Batesly) sits down with Jacqueline Schafer (Founder & CEO of Clearbrief) and Ashlee Drake Berry (Head of Legal at Casium) to discuss building AI tools for the legal profession. Honest, practical, and grounded in what actually works for a firm.

What We'll Get Into

Where AI genuinely helps a lawyer's day — and where it just adds risk

What it takes to earn trust with a profession that's right to be skeptical

How firms should think about the dozen legal-AI pitches landing in their inbox

What the next few years actually look like for legal tech

Who Should Come

Practicing lawyers

Legal-ops leaders

Founders and investors

Anyone curious about how AI reshapes a regulated profession

No technical background needed.

Format

A ~30-minute fireside conversation followed by open audience Q&A. Come with questions.

About Our Guests

Jacqueline Schafer — Jacqueline Schafer is the founder and CEO of the leading litigation drafting platform in Word, Clearbrief.ai (2026 Legalweek Litigation Product of the Year, Legalweek Tech for Good Winner 2026, 2025 Clio Best Practice of Law App, 2025 Compliance Solution of the Year), and a Lecturer in Law at Columbia Law.

The Legalweek Awards recently recognized Schafer as its 2025 Innovator of the Year, and the American Bar Association named her a 2025 Legal Rebel for Clearbrief's platform that catches AI hallucinations and helps litigators, arbitrators, in-house investigators, and judges write and file legal writing with hyperlinked citations to the evidence. She serves as one of the inaugural members of the Texas Bar's AI Taskforce and the WA Bar's Legal Technology Committee, and as a Board member of the nonprofit Scale Justice.

Her contributions to legal innovation have been recognized by LawDragon (2024 Leading AI and Tech Advisors), the ABA (2022 Women of Legal Tech), Fastcase (2022 Fastcase 50, Honoring 'Innovators, Techies, Visionaries and Leaders' in Law), and the Washington State Bar (2021 APEX Award for Legal Innovation).

Ashlee Drake Berry — Ashlee Drake Berry is the Head of Legal at Casium, an AI-native law firm and technology platform, which got its start at the AI House in Seattle. Casium modernizes employment-based immigration for high-growth companies, including early-stage founders navigating their own visa and compliance needs. Berry works closely with Casium’s product and engineering leadership to design human-in-the-loop AI immigration workflows that deliver personalization at scale — because immigration is an inherently human and deeply personal process that no amount of automation should ever lose sight of.

Before Casium, Berry was Principal Corporate Counsel at Microsoft, advising HR and business leaders on immigration matters affecting thousands of visa-enabled employees. Earlier, as one of the first U.S. hires at a $1B global immigration firm entering the American market, she was appointed to its advisory committee for the creation of I-9 compliance software.

With nearly 15 years of practice across six jurisdictions, Berry holds a J.D. from the University of Mississippi School of Law, an M.S., and an Executive M.P.A. She volunteers with Worldwide ERC’s Immigration Policy Forum and is licensed in Washington, Hawaii, Arizona, D.C., Tennessee, and Mississippi. She lives in Seattle with her spouse, three kids, and rescue dog, Lady.

About the Moderator

Rachel Bender is a Washington attorney and Co-Founder & CEO of Batesly, the matter-centric practice management platform built for the way lawyers actually work — because serious professional work deserves systems worthy of the responsibility that lawyers carry.

Prior to Batesly, Bender was Product Counsel for a social-good tech startup after spending nearly a decade in private practice, focusing on complex litigation, including serving as co-lead counsel on the largest class action against a state agency in Washington's history.

In 2025, Bender was named on the 'Ones to Watch' list by Best Lawyers in America and has been named a Rising Star by Super Lawyers Magazine every year from 2018 to 2026. In 2023, the Puget Sound Business Journal featured Bender as an Honoree for the Next Gen in Law Series.

Bender holds a J.D. from Seattle University School of Law and a B.A. from the University of Houston. She's licensed in Washington State and in the U.S. District Court for the Western District of Washington.

Free and open as part of Seattle Tech Week 2026