Chase (McCormack) C.

U.S. Legal Subject Matter Expert and AI Trainer

Pensacola, United States

Experience

Sep 2025 - Present
3 months
Remote

Legal Subject Matter Expert

Outlier AI

Leverage assessed legal expertise and proprietary AI training protocols to develop complex prompts and rubrics targeted at training Large Language Models (LLMs) to accurately identify, analyze, and respond to complicated questions of U.S. Law using calibrated legal reasoning.

May 2025 - Present
7 months
Pensacola, United States

Legal Intelligence Analyst / AI Trainer

Education Mercor

  • Qualified by assessment of legal expertise for intelligence analyst position.
  • Utilized legal expertise and proprietary AI training protocols in metrics to develop complex prompt scenarios and rubric grading criteria to train Large Language Models (LLMs) to accurately identify, analyze, and respond to complex questions of U.S. Law using calibrated legal reasoning.
May 2025 - Jul 2025
3 months
Pensacola, United States

Law Domain Expert / AI Trainer / Consultant

Nova Southeastern University After Query

  • Engaged by Y-Combinator backed startup to consult and assist in developing training protocols, metrics, environment, and tools to develop a best-in-class LLM for application in the legal field.
Apr 2025 - May 2025
2 months
Pensacola, United States

Domain Expert / AI Trainer (U.S. Law)

Toloka AI (Mindrift)

  • Utilized assessed legal expertise and proprietary AI training protocols in project procedures.
  • Trained Large Language Models (LLMs) to accurately identify, analyze, and respond to complex questions of U.S. Law using calibrated legal reasoning.
  • Worked as user on platforms including ChatGPT, Claude, Gemini, Deep Seek, Dall-E, Smith AI, Alexi, and Spellbook.
  • Conducted research and analysis across legal, scientific, technical, medical and other topics, and absorbed new complex concepts to independently establish expertise.
  • Demonstrated oral advocacy, public speaking and legal, technical, and creative writing.
Jan 2024 - Dec 2025
2 years
Pensacola, United States

Senior Associate Attorney

Lloyd, Gray, Whitehead & Monroe, P.C.

  • Oversaw a diverse, high-volume caseload, driving successful transactional outcomes and successful litigation at the trial and appellate levels.
  • Crafted innovative case plans and budgets, creating win-win attorney-client relationships through unique fee structures.
  • Emphasized decentralized command, ownership, and agile decision-making while maintaining constructive project oversight.
  • Cultivated a robust understanding of multifaceted legal, scientific, business, and technically complex issues.
  • Articulated data-driven analyses and actionable recommendations accounting for human factors to guide clients through complex litigation challenges.
  • Leveraged hands-on experience to protect client interests while encouraging realistic expectations and emotional clarity.
Jan 2019 - Dec 2024
6 years
Pensacola, United States

Associate Attorney

Whibbs, Stone, Barnett & Turner, P.A.

  • Established versatile legal consultancy, offering dynamic business and transactional solutions merged with consistent courtroom advocacy to empower client success.
Jan 2017 - Dec 2019
3 years
Pensacola, United States

Founder / Managing Attorney

CMC Law Firm, PLLC

  • Established a solo law practice, successfully advocating for individuals and businesses in commercial litigation, transactional negotiation and corporate governance.
  • Chosen as counsel for novel and complex cases across diverse practice areas based on demonstrated ability to craft creatively sound arguments and innovative legal strategies for successful resolutions.
Jan 2015 - Dec 2017
3 years
Tampa, United States

In-House Corporate Counsel

Syniverse Technologies, LLC

  • Provided strategic legal representation to a global leader in cross-platform mobile networking solutions in matters involving corporate governance, high-value tech and telecom transactions, and other complex negotiations involving Fortune 500 and 100 companies and international government agencies.
  • Directed a collaborative revenue recovery campaign with Finance, reclaiming over $5 million from global telecommunications firms and government agencies.
  • Collaborated with C-Suite executives to assess offsite data storage facilities based on demonstrated technical acumen.
Jan 2013 - Dec 2015
3 years
Tampa, United States

Regional Attorney Manager

Phelan, Hallinan, Diamond & Jones

  • Directed complex mortgage foreclosure cases for major institutional clients, minimizing risks and maximizing recovery rates.
  • Recognized as 'Most Valuable Attorney' within one year for outstanding litigation results and client advocacy.
  • Selected to manage the firm's most complex and contested cases, successfully resolving approximately 2,000 litigated matters.
  • Transformed litigation efforts in key Florida regions, empowering a team of 35 attorneys and support staff to exceed client expectations with outstanding results.
  • Facilitated discussions with clients and legal counsel, navigating complex settlement negotiations and case resolutions.

Summary

Lifelong autodidact with fifteen years of experience as a practicing attorney leveraging extensive legal experience as domain and subject matter expert to develop and train AI / Large Language Models (LLMs) with the potential to revolutionize and democratize the legal field through machine-based legal reasoning and cognition.

Languages

English
Native

Education

Oct 2013 - Jun 2015

University of Alabama School of Law

Master of Laws, Business Transactions · Tuscaloosa, United States

Oct 2005 - Jun 2008

Nova Southeastern University Shepard Broad College of Law

Juris Doctor · Law · Fort Lauderdale, United States

Oct 2000 - Jun 2005

University of Florida

Bachelor of Arts · English · Gainesville, United States

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