Best of 2024: Can AltFee Kill the Billable Hour and Bring Transparency to Legal Billing? (Scott & Digby Leigh)
Technically Legal - A Legal Technology and Innovation Podcast
Release Date: 12/18/2024
Best of 2025 - From IP Lawyer to Investor to CEO to Legal Ecosystem Builder (Avaneesh Marwaha, Litera CEO)
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...
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Best of 2025 - Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)
Technically 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...
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Best of 2025: The Future of Real Estate is Here (and It's on Blockchain) -Daniel Rollingher (GC Fabrica)
Technically Legal - A Legal Technology and Innovation Podcast
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Best of 2025: Building and Documenting Better Legal Workflows: Insights from Systemology Author David Jenyns
Technically 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. ...
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Future-Proofing Legal Ops: AI Literacy, Innovation and Augmentation (Meredith Kildow, President Consilio)
Technically 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...
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Beyond ChatGPT: Why In-House Counsel Need Purpose Built AI (Cecilia Ziniti, CEO - GC AI)
Technically 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...
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From 'No' to 'Go': How AI Guardrails Drive Trust, Enabling Legal to be a Business Accelerant, Not Blocker (Sabastian Niles, Salesforce President & CLO)
Technically 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...
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Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)
Technically 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...
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Want to be a Crypto Lawyer? Rule # 1: Use the Technology. Rule #2: Beware of Hyper-Specialization (Justin Wales-Head of Legal, Crypto.com & Author of Crypto Legal Handbook)
Technically 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...
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The Business of Law: From IP Lawyer to Investor to CEO to Legal Tech Ecosystem Builder (Avaneesh Marwaha, Litera CEO)
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_outlineIn this Best of 2024 episode, we revisit our conversation with Scott and Digby Leigh, founders of AltFee—a legal tech startup tackling one of the industry’s biggest challenges: the billable hour.
Despite decades of debate, the billable hour still dominates legal billing. Enter AltFee. The app helps legal professionals scope, price, and manage projects using alternative fee arrangements (AFAs), offering clients more transparency and value.
Scott and Digby highlight why AFAs matter now more than ever: as AI reduces time spent on tasks, value-based pricing will become essential. AltFee provides a foundation for law firms to shift away from time-based billing, encouraging lawyers to focus on the actual value of their services—not just the clock. From scoping projects to auditing fees, this conversation explores the future of legal pricing and how AFAs can reshape client relationships for the better.
If you’re curious about innovation in legal tech, or if you’re tired of the constraints of hourly billing, this episode is a must-listen.
Episode Credits
Editing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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