Navigating the Legal Tech Landscape: Insights from the 2023 Ari Kaplan Advisors CEO Roundtable

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Navigating the Legal Tech Landscape: Insights from the 2023 Ari Kaplan Advisors CEO Roundtable

In the ever-evolving legal technology landscape, the 2023 Ari Kaplan Advisors CEO Roundtable brought together industry leaders to discuss opportunities, challenges, and the future trajectory of the legal sector. Hosted by industry analyst Ari Kaplan, the roundtable featured CEOs from prominent companies, providing a glimpse into the pulse of the legal tech industry. Read on for critical insights and revelations shared by the CEOs.

The Visionaries Leading Legal Tech

The CEOs in attendance represented a diverse range of legal tech companies and interests, each specializing in different aspects of the industry. Sheryl Hoskins, CEO of Litera, highlighted their focus on providing software tools to empower legal professionals. Other CEOs, such as Aviva Cuyler (JD Supra), Debbie Foster (Affinity Consulting), and Josh Blandi (Unicourt), offered unique perspectives on content marketing, business intelligence, and legal data services, respectively.

The Rise of Generative AI: A Game-Changer

One recurring theme throughout the roundtable was the emergence of generative AI and its transformative impact on the legal industry. The CEOs acknowledged a shift in attitudes, with lawyers increasingly enthusiastic about leveraging AI for contract review and other legal processes. Daniel Lewis, CEO of LegalOn, expressed excitement about the opportunities associated with generative AI. 

Sheryl Hoskins emphasized the creativity sparked by generative AI, citing Litera’s “Project Dragon” as an example—a deal-point extraction solution born from customer feedback and pain points. The sentiment was echoed by Josh Baxter, CEO of NetDocuments, who emphasized the need to integrate AI solutions seamlessly into existing workflows to maximize their adoption.

Unleashing the Potential of Generative AI

The roundtable participants recognized the potential of generative AI to revolutionize the work of legal professionals. They discussed the importance of initiating projects that enable necessary changes rather than implementing AI for its own sake.

Josh Blandi emphasized the industry’s shift toward viewing data as a core asset, enabling previously unconsidered use cases. This newfound emphasis on technology staff and enterprise data strategy departs from the priorities of just five years ago.

Addressing Concerns and Challenges

The CEOs acknowledged the need to address concerns and challenges as the legal industry embraces generative AI. Sheryl Hoskins highlighted the crucial role of education in dispelling misconceptions surrounding AI. Josh Baxter emphasized the delicate balance between fear and excitement, anticipating a potential disillusionment phase in 2024 if customers aren’t guided through the transformative journey of adopting generative AI.

Kelly Griswold of Onna echoed the sentiment, emphasizing the importance of tying generative AI capabilities to tangible outcomes and use cases. The CEOs collectively recognized the need for continuous education, not just on the capabilities of AI but also on its real-world applications and impact.

Skills for Thriving in 2024

The CEOs unanimously agreed that communication skills are paramount in navigating the opportunities and challenges presented by AI. They stressed the need for effective communication to align expectations on AI projects, acknowledging the fine line between optimism and potential disillusionment.

Debbie Foster highlighted a unique challenge—bar associations getting involved in regulating how lawyers bill for work that applies generative AI. Smaller firms with fewer resources face the additional hurdle of implementing guardrails for AI usage.

Anticipating the Future: 2024 and Beyond

The participants expressed optimism for 2024, expecting continued positive growth. Eric Thurston (SurePoint Technologies) emphasized the need to manage talent and create a culture conducive to organic growth and mergers. Aviva Cuyler shared insights into how AI adoption influences content creation and provided recommendations for law firms.

Generative AI stands as a powerful force reshaping the legal landscape. These CEOs envision a future where the seamless integration of technology and human expertise leads to enhanced quality and productivity across the legal sector. Effective communication, continuous education, and a strategic approach to AI adoption will be the keys to success in 2024 and beyond.

For a more in-depth view of the conversation, listen to the podcast here.