Ep 298: SpotDraft’s Shashank Bijapur: From Late-Night Due Diligence to Legal Tech Innovation
Release Date: 07/29/2025
LawNext on Location: Visiting Everlaw’s Headquarters For A Conversation with AJ Shankar, Founder and CEO
LawNext
For the final installment of our LawNext on Location series, Bob heads across the bay, from San Francisco to Oakland, to the headquarters of e-discovery company Everlaw, where he sits down with founder and CEO AJ Shankar for a conversation about technology, AI and being in it for the long game. AJ grew up in Connecticut, came west in 2002 for a computer science PhD at UC Berkeley, and has lived within a few blocks of the Berkeley campus ever since. He stumbled into the legal industry almost by accident — recruited to serve as a technical expert in litigation involving how the internet...
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LawNext on Location: At A Sonoma Winery, A Conversation with Briefpoint CEO Nathan Walter about Discovery, Disruption and, Of Course, Wine
LawNext
Continuing his on-location interview tour of San Francisco, Bob heads an hour north to Santa Rosa to sit down with Nathan Walter, cofounder and CEO of Briefpoint, over a bottle of red wine at Paradise Ridge Winery, a spot literally around the corner from Nathan's house, sitting on the edge of the Mayacamas Mountain Range that divides Sonoma and Napa counties. It is a fitting setting for a founder who grew up in Sonoma wine country, where wine is less a luxury than a way of life, and where his family's most treasured heirloom was a bottle from the year he was born. Nathan's path to...
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LawNext on Location: The View from Tiburon – A Conversation with Pablo Arredondo, Casetext Cofounder
LawNext
As Bob continues his LawNext on Location series – all recorded live in the San Francisco area at locations of each guest’s choosing – he sits down with Pablo Arredondo at his home in Tiburon, a quaint Marin County town with a history stretching from Mexican land grants to naval outposts to a southern railway terminus. From Pablo’s home office, the view looks out over Richardson Bay towards Sausalito and, if you look carefully, the Golden Gate Bridge can be seen in the distance. It is a setting that is entirely fitting for a conversation with someone who helped shape one of the more...
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LawNext on Location: Lunch with Alex Su of Latitude Legal In Alameda, Calif.
LawNext
This episode is recorded live, and is best enjoyed on YouTube. . While Bob is visiting San Francisco for two weeks, he is sitting down for conversations with legal tech innovators and entrepreneurs “in their natural habitats” – places in the Bay Area they consider special. Today, in the first in this series, Bob sits down for lunch with , chief revenue officer at , over Thai iced tea and tofu dishes at Phnom Penh House, a Cambodian restaurant in Alameda that Alex considers something of a personal institution, frequenting it for both family meals and business meetings. ...
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From Customer to Acquirer: Filevine's Ryan Anderson and Pincites' Sona Sulakian on Building AI Contract Intelligence
LawNext
In this episode of LawNext, we talk with Ryan Anderson, co-founder and CEO of Filevine, and Sona Sulakian, former CEO and co-founder of Pincites, about Filevine's acquisition of the AI-powered contract redlining company. The deal, which closed in December, marks Filevine's second major AI acquisition of the year. Even more notably for this traditionally litigation-focused company, it represents a significant strategic expansion into the corporate and transactional legal market — a segment where Filevine saw 120% growth in 2025. What makes this acquisition particularly compelling is its...
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From Roommates to Billionaires: Harvey's Founders Gabriel Pereyra and Winston Weinberg on Building AI Infrastructure for Law
LawNext
Gabriel Pereyra and Winston Weinberg started legal AI company Harvey in 2022 as roommates in a San Francisco apartment. Pereyra had been working on AI research at Meta and Google, while Weinberg was a first-year litigation associate at O'Melveny & Myers. Today, they still share that same apartment, but their company has grown into a global enterprise serving more than 1,000 law firms and corporate legal departments and valued at a whopping $8 billion. In this episode of LawNext, Pereyra and Weinberg take us back to Harvey's earliest days, when they were sending thousands of LinkedIn...
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Clio Doubleheader: CMO Reagan Attle and VP of Payments A.J. Axelrod
LawNext
In the last in a series of interviews recorded during the ClioCon conference in Boston in October 2025, we bring you a doubleheader – two interviews with two of the legal tech company’s key executives. In the first, LawNext host Bob Ambrogi speaks with , chief marketing officer at Clio since 2017. In a year in which Clio made the biggest acquisition in legal tech history with its $1 billion purchase of vLex, and in which Clio is aiming to dramatically expand its market and its use of AI, what are the challenges and opportunities for the person tasked with leading the company’s...
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Fastcase Founder Ed Walters On the Implications of Clio’s Acquisition of vLex
LawNext
The biggest deal of 2025 – in fact, the biggest deal ever in legal tech – was legal tech company . A global legal research company founded in Spain, vLex had, just two years earlier, , and the union of those two companies – which also included the Docket Alarm trove of court docket data – had further accelerated the development of Vincent, vLex’s generative AI technology. Now, with Clio’s acquisition of vLex, comes a combustible combination that has the potential to unify the fuel of all that vLex legal research and docket data with Clio’s cloud practice management...
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Inside Clio's AI-Driven Transformation: CPO John Foreman and CTO Jonathan Watson
LawNext
For legal technology company Clio, this was a particularly significant year, marked by major announcements – including its $1 billion acquisition of vLex – that many saw as transformative for the company. This was on full display at the company’s ClioCon conference in October, where CEO Jack Newton gave a keynote laying out the company’s vision for a in which Clio becomes an “intelligent legal work platform” that serves not as a system of record, but as a system of action, powering lawyers through their workdays by automating much of what they do. In today's episode,...
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Reimagining Litigation Workflows through AI: A Panel Recorded Live at the Everlaw Summit
LawNext
As new tools using generative AI promise to change the way we litigate and conduct discovery, what are the implications for day-to-day litigation workflows? On today’s episode of LawNext, we feature a conversation with three guests about how law firms are navigating the urgency around gen AI adoption while staying grounded in practical realities. LawNext host Bob Ambrogi recorded this conversation at e-discovery company annual Summit in San Francisco, where gen AI was very much the talk of the conference — from new product announcements to candid discussions about how law firms are...
info_outlineWhat happens when a Harvard-trained corporate lawyer, tired of copying and pasting contract language, starts reading about self-driving cars? In Shashank Bijapur's case, it sparked the creation of SpotDraft, a contract lifecycle management company that just raised $54 million in Series B funding and that counts major companies such as Airbnb among its customers.
In this episode of LawNext, host Bob Ambrogi sits down with Bijapur, CEO and cofounder of SpotDraft, to explore his journey from White & Case associate to legal tech entrepreneur. It all began with that pivotal New Year's Eve moment – working on due diligence while eating Chinese food and reading about Elon Musk's self-driving cars – that made him realize something fundamental: Cars were driving themselves but lawyers were still stuck copying and pasting contract language.
The conversation traces SpotDraft's evolution from its original version as an AI redlining platform to becoming a comprehensive CLM solution. Bijapur shares the hard-won lessons of pivoting when their initial AI approach proved only as accurate as a coin toss, and how co-building with early customers who believed in their vision helped shape the product into what it is today.
They also dive deep into how generative AI is transforming contract management, get a preview of SpotDraft's new AI assistant called Sidebar, launching to the public next month, and discuss practical implementation challenges based on insights from SpotDraft's recent survey on AI adoption in legal departments. Looking ahead, they discuss where the CLM market is heading in the age of generative AI.
Throughout the discussion, Bijapur reflects on the entrepreneurial journey itself – learning to sell when trained to be demure, developing an appetite for risk after being taught to be risk-averse, and discovering that every startup milestone brings new challenges that require completely different approaches. It's a candid look at both the technical and human sides of building a legal tech company.
Thank You To Our Sponsors
This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.
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Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.
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Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).
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Paxton, Rapidly conduct research, accelerate drafting, and analyze documents with Paxton. What do you need to get done today?
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