Our Leadership Team

  HARRY BUCK is the Founder and CEO of Legal Outsourcing 2.0. He oversees the operations in the United States from New York. His mission is to help guide Legal Outsourcing 2.0 to become the best LPO in the world. The quality of the service we provide is the metric by which he is judged.

Harry practiced law, mostly as a litigator, for about 15 years. During that time, he was twice elected as a State Bar Commissioner and he was also elected as a member of the American Board of Trial Advocates.

Harry’s first job in legal technology was with Document Technologies (now Epiq) in 2005. He was certified as a Litigation Support Professional and designed and sold discovery and document solutions for large law firms and corporations. He also worked for a couple smaller eDiscovery companies in New York before working in legal outsourcing.

Harry’s first job in legal outsourcing was in 2007, during the early days when legal outsourcing was a novelty and not well executed. He largely learned what did not work and why. After a couple years at a legal outsourcing solutions provider, Harry provided counsel to large IT companies and law firms interested in setting up a legal outsourcing function.

Harry left the legal outsourcing space and became a VP of Sales and Marketing for a legal productivity software company and later a Director of Growth and Partnership for a legal AI company, LegalSifter. While working for LegalSifter he was approached by a group that knew of him from his legal outsourcing days. Shortly thereafter Legal Outsourcing 2.0 was formed and Harry became its CEO.  LegalSifter became the company’s first client.

Under Harry’s guidance, the company has already begun to hit its stride.

The company’s initial focus was to help create high quality data from which algorithms could be developed for legal concepts.  We have helped develop close to 1,000 algorithms from early stage LegalSifter to a Global 100 electronics giant.

As a consequence of helping develop legal AI tools, we have developed expertise in creating deliverables by using the tools we helped develop and keep a team busy doing that.

We do litigation document reviews on behalf of smaller clients and small law firms to Global 100 clients with Amlaw 50 law firms.

Additionally, we perform data breach notification document reviews for several of the largest cyber security consultancies in the world and are one of only two data breach review partners of Canopy, the tool of choice for performing data breach analysis.

Harry received his BA from Brown University and his JD from Pace University School of Law.

He has been certified as a litigation support professional.

In his spare time, Harry serves as the president of the Metro NY Chapter of ACEDS.

DAKOTA PRAKASH operates from Pittsburgh, Pennsylvania and is a seasoned contract operations professional and AI-enabled legal services expert.

With over eight years of experience in the legal field, Dakota brings a wealth of knowledge and expertise in contract operations, having worked across law firms, government agencies, and the software industry. Specializing in AI-assisted contract management for the past five years, Dakota has successfully integrated cutting-edge legal technology to streamline and optimize contract operations for clients across diverse sectors, including healthcare, manufacturing, shipping and supply chain, and software.

Holding a certificate in Paralegal Studies from the state of Pennsylvania, Dakota combines a strong legal foundation with a deep understanding of the practical applications of artificial intelligence in legal services. This unique blend of skills has positioned Dakota as a trusted leader in driving AI-enabled contract solutions, transforming how legal teams and organizations manage and execute contracts.

Proven results and a commitment to innovation define Dakota's approach, making her a key driver of success in enhancing contract operations, improving efficiencies, and delivering measurable outcomes for clients. 

 NAMRATA DUTTA operates from our India office and is a distinguished Director of Business Operations at ContractRedlining. With over a decade of unparalleled expertise in contract management, negotiation, and regulatory compliance, she is a consummate professional adept at navigating intricate contractual landscapes across diverse sectors, including technology, healthcare, pharmaceuticals, and finance. Namrata has played a pivotal role in architecting and executing sophisticated contract management frameworks, particularly in the realm of AI-assisted contract governance, revolutionizing efficiency and precision in legal operations.

At ContractRedlining, Namrata is the driving force behind the strategic alignment of contractual engagements with the company’s long-term vision, ensuring that each agreement is meticulously curated to facilitate seamless project execution, risk mitigation, and client success. Her exceptional prowess in client relations serves as the bedrock of her professional excellence, enabling her to forge and nurture high-value partnerships that elevate the company’s market stature and client satisfaction metrics.

Namrata’s illustrious career in the Legal Process Outsourcing (LPO) industry spans leadership tenures at globally renowned organizations such as Thomson Reuters, Xerox Business Solutions, and Consilio. At Thomson Reuters, she pioneered the optimization of legal document workflows, enhancing efficiency and precision in high-stakes contract review and compliance protocols. During her tenure at Xerox Business Solutions, she honed her project management acumen, successfully spearheading multifaceted, high-profile projects from conceptualization to execution. At Consilio, she demonstrated exemplary leadership in client services, overseeing key stakeholder engagements and ensuring the seamless delivery of bespoke legal solutions tailored to dynamic client needs. Her strategic foresight and client-centric approach have been instrumental in fortifying enduring client relationships and driving unparalleled project success.

Namrata holds a prestigious Bachelor of Laws (LL.B.) degree from Bharati Vidyapeeth Deemed University, Pune, India, earned in 2014, solidifying her foundation in jurisprudence and legal acumen.

NAKUL NASA works out of our Noida, India office and is our Director of Dedicated Service Teams. He leads a dynamic team based in our India office, dedicated to extracting complex contractual provisions and requirements from vast contract repositories using cutting-edge AI tools. Nakul has gained significant experience in the legal process outsourcing space with Mind Merchants, American Cybersystems, Inc. etc. He excels in translating complex contractual information into easily understood formats, enabling clients to make informed decisions. Committed to delivering exceptional results, he thrives in dynamic environments that demand precision, adaptability, and innovative approaches. He is passionate about leveraging technology to drive efficiency and empower businesses in their contract management endeavours.

Nakul completed his BBA.LLB in 2016 and LLM in 2021 from ICFAI University, Dehradun.

ANIRUDDHA SARKAR works out of our India office as the Director for Contract Review. Aniruddha leads the development and preparation of Standard Operating Procedures (SOPs) and playbooks for our diverse range of clients, which serve as a vital role for standardizing and streamlining contract redlining and management practices across the organization. Aniruddha is responsible for client orientation, communication (external and internal), quality assurance and our meticulous reviewing processes to maintain the highest standards of accuracy and quality assurance for our clients. 

With 6+ years of extensive experience in legal document review and contract lifecycle management he has an eye for detail and a profound understanding of contract drafting, redlining and negotiating workflows. Aniruddha's proficiency in redlining documents and risk assessment has been instrumental in optimizing the contract processes and safeguarding our clients' corporate interests. Through his leadership in these areas, Aniruddha ensures that the contract management operations are not only efficient and effective but also aligned with the company's strategic objectives. His expertise in developing out AI-assisted redlining provides our clients with the most comprehensive and complete review of their agreements.

Aniruddha spearheads the training programs for the redlining process, ensuring that new resources are equipped with the knowledge and skills necessary for success in this critical aspect of contract redlining. 

Before joining ContractRedlining, Aniruddha has held senior positions within the legal departments of several multinational corporations, where he refined his skills in contract drafting, reviewing, negotiation and litigation. Aniruddha began his career journey in the year 2018 at DWF Mindcrest as a Legal Researcher. He joined Legal Outsourcing 2.0 as a Senior Legal Associate in the Contracts Management team in 2021. Aniruddha’s educational background traces to the year 2017 where he completed his BA.LLB (Honors) from Tripura Central University and he furthered his academic credentials with a Master of Laws (LLM)  in 2018 specializing in the Constitutional Law. 

AASHISH GUPTA operates from our Kolkata, India office as the Director of Contract and CLM Solutions, bringing forth an illustrious career spanning over a decade in both dynamic team environments and autonomous roles. As a leader in Contract Management at Legal Outsourcing 2.0, Aashish is distinguished for his unwavering pursuit of excellence, relentless innovation, and strategic foresight in navigating the complexities of legal operations.

Aashish possesses a multifaceted command over project governance, client engagement, people leadership, team orchestration, service quality enhancement, and operational optimization. His passion for pioneering efficiencies and surpassing client expectations positions him as an indispensable force in high-stakes environments, where he reengineers processes to ensure seamless, cost-efficient, and timely project execution.

Before joining Legal Outsourcing 2.0, Aashish refined his acumen at DWF and Infosys collaborating with industry titans across infotainment, pharmaceuticals, broadcasting, technology, and professional services. His leadership philosophy is anchored in collaborative synergy, transformative mentorship, and a culture of perpetual advancement. His unassailable expertise encompasses orchestrating intricate projects, spearheading high-performance teams, and driving operational metamorphosis.

His impressive portfolio includes steering Contract Management initiatives, such as Contract Drafting & Negotiation, CLM Implementation, and Contract Migration, alongside leading cutting-edge Legal Analytics endeavours. Aashish is deeply invested in leveraging avant-garde technology and artificial intelligence to revolutionize contract management, amplifying precision, efficiency, and strategic decision-making.