Daniel Calloway
@danielcalloway
Strategic attorney specializing in technology and regulatory compliance.
What I'm looking for
I am a strategic attorney and systems thinker with a passion for advising leading institutions at the intersection of law, technology, and organizational integrity. My experience includes helping Fortune 500 companies, financial institutions, and emerging AI platforms navigate regulatory complexities and implement ethical practices. As the creator of Callo’s Way and the REASON Framework, I bring a multidisciplinary approach to legal strategy, bridging compliance, governance, and human-centered design.
Throughout my career, I have demonstrated proven leadership in greenfield AI implementations and law firm innovation strategy. My advisory roles have included serving on the Advisory Board for Axiom Law, where I provide strategic insights on global talent and ethical governance. I have also led legal AI model evaluations at Thomson Reuters, ensuring quality control and effective integration of AI technologies into legal workflows.
Experience
Work history, roles, and key accomplishments
Legal AI SME Consultant
Thomson Reuters
Jan 2025 - Present (7 months)
Lead SME for legal AI model evaluation and grading. Direct quality control for legal content in Automated Answer Review (AAR) program. Partner with engineering teams on AI performance insights and rubric alignment.
Senior Counsel / Advisor
Axiom Law
Jan 2022 - Present (3 years 7 months)
Provided legal advisory support on KYC/AML issues and fund-related matters for a global asset manager. Reviewed and responded to inquiries regarding client onboarding and compliance risk. Drafted, negotiated, and reviewed NDAs and assisted with fund documentation and governance.
Founder
DANDO LLC
Jan 2019 - Present (6 years 7 months)
Founded DANDO LLC, encompassing Callo Advisory for emerging tech governance and ethical systems design, and Callo's Way, a multimodal empowerment framework. Developed the REASON Framework, a SSRN-published rubric for evaluating legal reasoning in AI models.
Associate Attorney
Slater, Slater, & Schulman
Jan 2024 - Present (1 year 7 months)
Provided victim advocacy expertise & complex litigation skills to support claims distribution & facilitate bankruptcy proceedings for the largest sexual abuse case in US history. Managed complex, individual caseload (100+), performed claims analysis, conducted plaintiff interviews & drafted case conclusions.
Staff Attorney
Cohen & Milstein
Jan 2023 - Present (2 years 7 months)
Conducted thorough reviews of corporate governance materials (SEC filings, board minutes, investor relations docs) & executed eDiscovery tasks, contributing to a $1B settlement & ensuring accurate evaluation of regulatory disclosures & investor communications.
Expert Consultant
RGP
Jan 2020 - Present (5 years 7 months)
Assisted a supervisory control group ensuring CFTC/NFA compliance; led assurance reviews and independently performed compliance testing. Coordinated front/middle/back-office functions to standardize remediation protocols & stakeholder training.
Staff Attorney
Levin Papantonio Rafferty
Jan 2019 - Present (6 years 7 months)
Contributed to the $26B opioid litigation – 2nd largest class action in US history. Performed state analysis of applicable opioid litigation proceeds law; Executed in-depth HIPAA/privacy reviews & investigated documentation for potential corporate collusion.
Legal Consultant
Robert Half
Jan 2017 - Present (8 years 7 months)
Provided legal consulting for AML/Sanctions Audit at Wells Fargo. Supported sanctions surveillance and training as a consultant for the Association of Certified Sanctions Specialists.
Compliance Advisor
Capital One
Jan 2017 - Present (8 years 7 months)
Enhanced Enterprise KYC with senior executives, addressing OCC consent orders & CIP monitoring. Led procedural updates, QA audits, and AML BAU management (CIP, MLRA, third-party risk). Liaised with Legal on emerging risks (crypto, marijuana, elderly exploitation); authored AML Advisory Newsletter leveraging AI insights.
Program Manager
The Midtown Group
Jan 2014 - Present (11 years 7 months)
Liaised with the Department of Education under a White House Directive; oversaw 14 attorneys reviewing 35k borrower claims (fraud) at ~99% accuracy. Conducted training, instituted process improvements, & prepared state-law analyses.
Law Clerk
CACI International
Jan 2012 - Present (13 years 7 months)
Assisted the DOJ in the $18.7B Deepwater Horizon settlement. Organized trial exhibits, drafted post-trial briefs, & streamlined cite-checking for senior attorneys.
Education
Degrees, certifications, and relevant coursework
Harvard Law School
Executive Education Certificate, Computer Science for Lawyers
2025 -
Pursuing an Executive Education Certificate in Computer Science for Lawyers.
Berkeley Law
Certificate, Commercial Contracts; Artificial Intelligence
2023 - 2025
Completed certificates in Commercial Contracts and Artificial Intelligence Institute.
Columbia Business School
Certificate of Business Excellence, Global Banking & FinTech
2023 - 2023
Completed a Certificate of Business Excellence with alumni status, focusing on Global Banking & FinTech.
Columbia Business School
Certificate, Blockchain in Business
2022 - 2022
Obtained a Certificate in Blockchain in Business.
University of Connecticut School of Law
Juris Doctor (JD), Law
2008 - 2011
Grade: CALI Award – Constitutional Law
Obtained a Juris Doctor degree, with a CALI Award in Constitutional Law.
University of Maryland
Bachelor of Arts (BA), Criminology & Criminal Justice
2003 - 2007
Earned a Bachelor of Arts degree with a focus on Criminology & Criminal Justice.
Tech stack
Software and tools used professionally
Availability
Location
Authorized to work in
Job categories
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