Do What the Bots Cannot: How AI Is Reshaping Legal Marketing, Data Analysis and Biz Dev, But Not the Human Connection (Gyi Tsakalakis, AttorneySync)
Technically Legal - A Legal Technology and Innovation Podcast
Release Date: 08/28/2025
Technically Legal - A Legal Technology and Innovation Podcast
Avaneesh Marwaha, the CEO of , visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law. The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company to its current role as a comprehensive legal tech ecosystem. Avaneesh highlights the company's strategic shift from acquiring to building new technologies. He also emphasizes the importance of Litera’s...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
In one of the most popular episodes of the year, Founder discusses her organization's research that tests whether artificial intelligence custom-made for legal tasks better than general AI tools. Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleagues quickly revealed a strong community interest in a systematic approach to evaluating legal AI tools. This led to the creation of Legalbenchmarks.AI, dedicated to finding out where...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
In the most listened to episode of 2025, author of "" and business systems expert, , discusses the importance of systemizing business processes, even in the nuanced field of law. Jenyns debunks the myth that legal work is too bespoke to be systemized, explaining how just like any other business, documenting legal workflows unlocks scalability and creativity. He shares his journey from digital SEO agency owner to becoming a systems expert and outlines the seven steps of his Systemology framework. Key Topics: The importance of documenting processes in any business, including legal services. ...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
Meredith Kildow, President of Consilio discusses her career path from finance to leading global operations and delivery for one of the largest companies in the legal and eDiscovery space. Meredith shares insights into building a revenue organization from the ground up and the shift to her current role overseeing operations and delivery for a highly acquisitive company. The conversation focuses on the practical, present-day applications of Artificial Intelligence (AI) in the legal industry, examining how it’s moving beyond "innovation theater" to drive ROI, efficiency, and cost reduction in...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
This episode features a conversation with , Co-Founder and CEO of . Cecilia traces her career from early the early days of the internet to founding an AI-driven legal platform for in-house counsel. Cecilia shares her journey, starting as a paralegal at Yahoo in the early 2000s, working on nascent legal issues related to the internet. She discusses her time at Morrison & Foerster and her role at Amazon, where she was an early member of the Alexa team, gaining deep insight into AI's potential before the rise of modern large language models (LLMs). The core discussion centers on the creation...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
In this episode, , President and Chief Legal Officer at , takes a deep dive into the intersection of corporate strategy, in-house legal careers, and the transformative power of Agentic AI. Sabastian shares his unique career path from a near two-decade tenure at a prestigious law firm before joining Salesforce. This conversation is essential for anyone interested in the evolving role of the Chief Legal Officer and the practical application of cutting-edge technology in legal operations. Things We Talk About in this Episode The In-House Career Journey: Sabastian’s path highlights an early...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
Is artificial intelligence custom-made for legal tasks better than general AI tools like Google Gemini and ChatGPT? That is the topic of this episode featuring Founder . Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleagues quickly revealed a strong community interest in a systematic approach to evaluating legal AI tools. This led to the creation of Legalbenchmarks.AI, dedicated to finding out where the promise of humans plus AI is...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
, Head of Legal for the Americas at Crypto.com, and author of visits the show to provide his unique perspective on pivoting from a career in Constitutional Law, including work on high-profile appellate cases like the Obergefell gay marriage decision, to becoming a trailblazer in crypto law and blockchain technology. He shares his serendipitous journey stemming from a law school article that launched his legal career and his subsequent deep dive into crypto, sparked by WikiLeaks accepting Bitcoin donations. The discussion covers the evolution of his practice to one of the first...
info_outlineTechnically Legal - A Legal Technology and Innovation Podcast
Avaneesh Marwaha, the CEO of , visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law. The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company to its current role as a comprehensive legal tech ecosystem. Avaneesh highlights the company's strategic shift from acquiring to building new technologies. He also emphasizes the importance of Litera’s...
info_outlineWe welcome back legal marketing expert Gyi Tsakalakis, President of AttorneySync and host of the Lunch Hour Legal Marketing podcast. Five years after Gyi’s first appearance on Technically Legal, he discusses the dramatic shifts in digital marketing for law firms, driven largely by the rise of artificial intelligence.
Gyi highlights how AI is changing the landscape for lawyers, from automating back-office functions and data analysis to influencing content creation and search engine optimization (SEO). He explains why law firms must diversify their marketing channels beyond just Google to adapt to the new era of conversational search and AI overviews. Despite these technological advances, Gyi emphasizes that the human connection, including a simple handwritten note, remains the most powerful tool in an attorney's arsenal. He argues that as technology automates the mundane, it forces lawyers to focus on the relationships and empathy that truly differentiate their practice.
Key Takeaways:
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Diversify Marketing Channels: Law firms must move beyond a "one-trick pony" approach with platforms like Google and diversify their client acquisition strategies to include social media, email, and local events.
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The Problem with Client Intake: Gyi discusses the persistent issue of lawyers not responding to inquiries and how AI can help automate certain parts of the intake process, though the human touch is still crucial for building trust.
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Do What the Bots Cannot: Attorneys should leverage AI for tasks that can be automated (e.g., scheduling, data analysis) to free up time to focus on complex legal work and building meaningful client relationships.
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AI for Data Analysis: A powerful, overlooked use case for AI in a law firm is analyzing internal data, such as call transcripts and financial records, to identify blind spots and inform marketing strategies.
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The Future of SEO and Search: Gyi predicts that search will become more conversational and influenced by AI Overviews and that ad-based models will be integrated into all major AI platforms.