Free Law Project at ILTACON 2025: Navigating the "Accidental Project Manager" Journey

This August marked a first for Free Law Project: our inaugural appearance at ILTACON, one of the largest and most influential conferences for legal technology professionals with more than 4,000 attendees. I was honored to represent the organization, both as an attendee and as a presenter, and to share space with colleagues who are shaping the future of legal technology.

Session Spotlight – The Accidental Project Manager: Charting Uncharted Waters

I spoke on a panel titled “The Accidental Project Manager: Charting Uncharted Waters,” which explored what it means to step into project management roles unexpectedly. Many of us in legal technology didn’t plan to become project managers—yet the work often requires coordinating projects, balancing competing demands, and guiding teams through change.

For me, these lessons are directly tied to Free Law Project’s mission. I shared how managing complex initiatives like the Litigant Portal—our open-source tool designed to help self-represented litigants navigate court—requires careful planning, collaboration, and user-centered design. By weaving access to justice goals into project management, we ensure that innovation doesn’t just serve institutions, but the people most in need of equitable access to the courts.

Our discussion focused on:

• Strategic planning for legal tech projects: structuring work so projects succeed in fast-paced environments.
• Managing stakeholders: bridging gaps between attorneys, technologists, and business leaders.
• User-centered delivery: ensuring that innovation remains grounded in accessibility and real-world usability.
• Lessons learned: how “accidental” project managers can grow into the role and bring unique value to their organizations.

I was joined by an excellent group of panelists who brought perspectives from across the legal sector:

• Stephanie Clerkin – Director of Litigation Support, Korein Tillery LLC
• Ashley Gibbs – Senior Director, Product Value Engineers, Litera
• Amanda Miller – Operations Manager – Digital, Nissenbaum Law Group, LLC
• Stephen Reale – Manager of Program Management and Business Analysis, Ropes & Gray

Together, we highlighted how project management has become a core skill for driving legal technology forward—even for professionals who never set out to hold the title.

Recognizing Scholarship and Collaboration

It was also meaningful to attend ILTACON with my colleague, Jenifer Whiston, who was selected as a Cheryl Disch Diversity, Equity & Inclusion Scholarship recipient this year. Her participation brought an important perspective to our time at the conference and underscored the value of broadening representation in legal technology.

Beyond the scholarship, Jenifer’s role as Free Law Project’s Director of Philanthropy opened doors to conversations with leaders from major law firms, exploring how they can partner with us to strengthen legal transparency and expand access to justice. These connections are essential as we continue building a sustainable future for open law and open technology.

Scenes from ILTACON

Key Takeaways

• Project management is everywhere: Even without formal training, many professionals in legal tech find themselves managing complex projects.
• Different perspectives strengthen outcomes: Our panel showed how law firms, vendors, and nonprofits share challenges—and can learn from each other’s approaches.
• Conferences build community: ILTACON provided opportunities for dialogue, learning, and collaboration across the profession.

Looking Ahead

Free Law Project’s first ILTACON was both a milestone and a reminder of why our work matters. The panel on The Accidental Project Manager showed how diverse perspectives on project management can spark new approaches—and it gave me the chance to highlight the Litigant Portal as a concrete example of innovation aimed at closing the justice gap. At the same time, Jenifer’s scholarship and her outreach to leaders from major law firms underscored how collaboration and partnership are essential to sustaining this mission. Together, these experiences point toward a future where strong project management, open technology, and committed partners work hand in hand to expand access to justice.