The AI Advantage: How Jackson Lewis Turned Data Into a Growth Engine

CHICAGO, IL – June 25, 2026

The legal industry, often perceived as a bastion of tradition, is quietly undergoing a data-driven revolution. A prime example of this shift is the recent recognition of Jackson Lewis P.C. with the 2026 Litera Foundation Innovation Award. While awards in the tech space are common, this one signifies something more profound: a tangible and successful strategy for converting a law firm's most underutilized resource—its own experience data—into a powerful engine for business growth. The firm's work offers a compelling case study in moving beyond the speculative buzz of artificial intelligence to achieve real-world competitive advantage.

Jackson Lewis, a national firm with over 1,100 attorneys focused on employment and labor law, didn't embark on this journey for the sake of innovation alone. The catalyst was a common, high-stakes problem: a critical business pitch was hampered by the inability to quickly access and articulate the firm’s deep, relevant experience. This moment of friction revealed that simply having data wasn't enough; the challenge was making it accessible, searchable, and useful. The firm’s response demonstrates a strategic pivot from reactive data retrieval to proactive intelligence generation.

From Pitch Problem to AI Solution

Recognizing that a simple system upgrade would not suffice, the team at Jackson Lewis, led by Trina diNapoli, Director of Marketing & Business Development Operations and Systems, reframed the problem. The core challenge wasn't just technical; it was operational. Attorneys, already burdened with billable work, lacked the time to manually draft detailed matter narratives for a central database. The solution lay in leveraging generative AI to do the heavy lifting.

In collaboration with LKO Information Management Consulting, the firm implemented a groundbreaking workflow within Litera Foundation, a platform designed to centralize firm experience data. The team used generative AI to automatically draft robust matter narratives directly from existing case documents. Crucially, this process was not an unguided black box. It was steered by carefully designed templates that shaped the AI's output, ensuring the narratives were structured, relevant, and aligned with the firm's strategic messaging.

This approach ingeniously solved the adoption hurdle. Instead of asking attorneys to write from a blank page, the system presented them with a well-formed draft for review and refinement. The result was a dramatic increase in enriched data. Over 30,000 matters within Litera Foundation now feature detailed profiles and searchable narratives. This repository has become an invaluable asset, providing business development teams and practicing attorneys with reliable, on-demand intelligence for pitches, proposals, and client work. As Trina diNapoli stated, “We’re committed to continuous improvement, always moving forward, and not waiting for perfection before taking action… I’m excited to take it to the next level, proving value every step of the way.”

The Human Element in a Digital Transformation

The success story at Jackson Lewis is not merely about sophisticated algorithms. It is a powerful testament to the importance of people, process, and partnership. The project's triumph hinged on the collaborative synergy between the firm's internal team and the external expertise of Lynn Oser, founder of LKO Information Management Consulting, who was instrumental in guiding the strategic implementation.

This partnership highlights a critical lesson for any organization undertaking a complex tech initiative: technology is a tool, but strategy and change management are the foundation. LKO's role extended beyond technical advice to encompass process improvement, information harmonization, and service excellence. The firm helped Jackson Lewis identify and integrate disparate, organic sources of matter data from across the organization, breaking down the information silos that plague so many large enterprises. This holistic approach ensured the technology served a clear business strategy: turning fragmented information into a leveraged, firm-wide asset.

The project underscores that successful innovation is rarely a solo endeavor. It requires internal champions like diNapoli who possess a deep understanding of the firm's needs and a vision for technology's potential. It also benefits immensely from external consultants who bring a fresh perspective, specialized knowledge in areas like information management, and a structured methodology for navigating change.

A Blueprint for the Broader Legal Industry

Jackson Lewis's achievement serves as a practical blueprint for a legal sector grappling with how to adopt AI effectively. For years, the conversation has been dominated by hypotheticals. This award, presented by Litera CEO Avaneesh Marwaha at the Trailblazers Summit 2026, celebrates a firm that is delivering tangible value now.

As Sean Munafo, Chief Revenue Officer at Litera, noted, “Differentiation today comes down to how effectively a firm can harness its data to clearly demonstrate where and how it creates impact for clients.” Jackson Lewis has done precisely that. Their initiative is part of a broader, deliberate strategy to embed AI into the firm's operations. The firm has developed a generative AI policy, provides foundational training, and even hosts internal "Prompt-a-thons" with Microsoft to build practical skills. This commitment to both tooling and training is essential for fostering a culture of responsible and effective AI adoption.

This work also provides a roadmap for overcoming common industry hurdles. By automating the creation of matter narratives, the firm directly addressed the persistent challenge of attorney adoption for knowledge management initiatives. By integrating various data sources, they tackled the problem of data silos. The project proves that with the right strategy, AI can be a powerful tool for enhancing attorney performance, sharpening client engagement, and making a firm's value proposition undeniable at every interaction. This is the new benchmark for data-driven business development in the legal field.