Shawn C. Helms

Overview

Shawn C. Helms is co-head of the firm’s Technology Transactions & Outsourcing Practice and co-founder of the firm’s AI Cross-Practice Group. Shawn also serves on the firm’s Management Committee.

Shawn has broad experience in the areas of information technology, outsourcing, artificial intelligence (AI), blockchain, crypto, digital health, and telecommunications. He focuses his practice on complex transactions involving technology and intellectual property, including information technology outsourcing (ITO), business process outsourcing (BPO), licensing, cloud computing arrangements (IaaS, SaaS, and PaaS), technology maintenance and services, technology development/customization, AI, generative AI (e.g., ChatGPT, Claude, Gemini, Copilot, Llama, and Bedrock), social media issues, strategic alliances, e-commerce, internet of things (IoT), wireless infrastructure, confidentiality, strategic sourcing, and data security/privacy. Shawn also has significant experience in advising clients through software audits and related negotiations and settlements, open source software issues, and software escrow matters.

Shawn has been working in the field of AI for more than 10 years and is the founding member of the McDermott AI Cross-Practice Group and resource center (ailawcenter.com). Shawn is regularly working with clients on issues related to leveraging generative AI, particularly in the implementation and utilization of cutting-edge technologies and emerging tools like agentic AI solutions.

Shawn has written widely on the topics of technology and outsourcing. In 2025, Shawn co-authored AI Law and Business published by American Lawyer Media / Law.com Scholar. This comprehensive legal treatise explores the legal and regulatory frameworks and business issues shaping AI in the US and globally, covering governance, IP, data privacy, ethics, risk, contracts, torts, antitrust, employment, and more, all through the lens of rapid technological change.

Shawn also has considerable experience in blockchain and cryptocurrency matters including NFTs, DAOs, and enterprise blockchain applications. Shawn regularly works on the transactional aspects of cryptocurrency bankruptcy and liquidation matters. Shawn also regularly works on digital health matters involving wearables, data licensing and strategy issues, AI, and mobile applications. Shawn also regularly advises clients on IT and IP diligence, transition services agreements (TSAs), and other technology and intellectual property matters relating to the acquisition or divestiture of businesses.

Shawn is the co-author of a legal treatise on outsourcing law, Outsourcing Law and Business published by Law Journal Press (the treatise publishing arm of American Lawyer Media). It is the only comprehensive treatise on outsourcing law. This treatise gives detailed treatment to all material legal and business issues associated with outsourcing transactions. Learn more at outsourcingtreatise.com. Shawn is also the co-author of a Bloomberg BNA portfolio titled “Technology and Outsourcing.”

Shawn worked as part of a team to create free, downloadable form Master Outsourcing Service Agreements (MOSA). This form MOSA is available at www.outsourcingmsa.com.

Previously, Shawn was a partner at an international law firm, in-house counsel at T-Mobile/Sprint, and the Chief Information Officer at Williams & Connolly. Shawn earned three bachelor’s degrees in computer systems, business administration, and economics.

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Results

Represented Amadeus, one of the top ten travel technology companies in the world, in an agreement with Marriott International to deploy the Amadeus Central Reservations System to modernize Marriott’s reservation infrastructure in the coming years.
Represented Ava Labs, the developer of the Avalanche blockchain (a layer-1 smart contract platform) in the creation of a blockchain subnet platform to be offered by Deloitte to their customers. This subnet platform will allow Deloitte customers to create their own blockchain solutions.
Counseled a large publicly traded technology company on revisions to a social media platform’s terms and conditions to allow for NFTs on its platform. This project involved strategic advice to the and revisions to the social media platform’s terms and conditions.

Represented MedStar Health in its comprehensive, 5 year, IT outsourcing deal with Kyndryl, the world’s largest IT infrastructure services provider. Under this deal, Kyndryl will provide mission critical IT capabilities across the MedStar Health system and accelerate its digital transformation. Kyndryl will provide ongoing healthcare technology services, including specialized clinical and IT service desks, infrastructure support, onsite technical support, network, and security services.
Advised Keys Token Inc. in their development and release of their Meta Mansion NFT offering (https://www.metamansionsbykeys.com/). This included advising on the giveaway of 888 Ethereum tokens to various holders of Meta Mansion NFTs including drafting the related terms and conditions.
Represented Finnair in a long-term, full-scope information technology outsourcing transaction with IBM whose scope encompassed all of the airline’s information technology (IT) functions, including infrastructure, server and workstation management, print, network (local area network (LAN) & wide area network (WAN)), application development and maintenance, service desk, enterprise platforms, cloud and cloud orchestration and service integration and management (SIAM).
Represented a leading outsourcing provider in a software resale transaction surpassing $100 million.
Represented Commerce Bank in their contract to purchase and implement of a new core banking system from Temenos. The core banking system will replace an aging system and will serve as the brain of the bank, managing all deposits and the majority of Commerce’s banking activities.
Represented Attachmate in its multibillion-dollar acquisition of Novell and the related sale and license back of Novell patents to a consortium of the world’s largest software companies, including Microsoft, Oracle, Apple and EMC.
Represented a European joint venture in an IT outsourcing agreement with a related entity; the transaction was a six-year, full-scale, global IT outsourcing agreement covering user care, back office, client system, data center and local area network services with a total deal value of well over $1 billion.
Advised a communications and health care services company in its joint venture to develop cloud-computing based medical image management solutions to one of the leading US health care institutions.
Served as primary outside counsel for a Boston-based software company that provides industry leading software to large financial institutions representing the company in its customer contracts and procurement transactions.
Represented a small software company in its agreement with Intel to provide wireless connection management services for Intel’s next generation mobile chipset to be utilized in smartphones, tablet personal computers, netbooks and other mobile devices.
Advised Texas Instruments in connection with its $6.5 billion acquisition of a semiconductor company.
Represented Infinite Computer Solutions in a transition that resulted in Infinite taking over the development, maintenance and support of a Motorola short message service (SMS) and multimedia messaging service (MMS) solution.
Advised a leading health care provider in the acquisition and licensing of an electronic medical records system for its inpatient and ambulatory facilities.
Represented ISG in the re-formulation of their form outsourcing RFX documents and related intellectual property.

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Recognitions

Best Lawyers in America, Information Technology Law, IT Outsourcing Law (2017-2026), Artificial Intelligence Law, 2026
Best Lawyers in America, Lawyer of the Year: IT Outsourcing Law, 2017-2025
Chambers FinTech, USA Nationwide: FinTech Legal: Blockchain & Cryptocurrencies, 2026