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Bobbi Rakova

Data Scientist
Palo Alto (Silicon Valley)
About

Bogdana Rakova is a data scientist in DLA Piper's Piper AI team, where her work focuses on AI evaluation pipelines, risk-aware legal workflows, agentic tools, and legal red-teaming.

Bobbi is not a lawyer.

Areas of FocusTechnologyTechnology and Commercial TransactionsRegulatory and Government AffairsIntellectual PropertyHealthcareSustainability
Education
  • Executive Program, Leading Successful Programs: Using Evidence to Assess Effectiveness, Harvard Kennedy School, 2020
  • Executive Program, Assembly: Ethics and Governance of AI, Harvard Berkman Klein Center and MIT Media Lab, 2018
  • Graduate Studies Program, Singularity University, 2014
  • B.S., Computer Science, Sofia University St. Kliment Ohridski, 2012

EXPERIENCE

  • Co-leads cross-functional projects and external collaborations on AI legal red-teaming, risk-aware legal workflows, and agentic tools internally and with clients
  • Develops responsible AI testing and evaluation methods, including legal red-teaming, safety guardrails, and socio-technical evaluation pipelines for generative and agentic AI systems
  • Works at the intersection of data science, law, policy, and trust and safety to help practitioners evaluate high-risk AI systems in healthcare, education, and law
  • Co-developed and communicated red-teaming methods for healthcare AI, including generative AI applications such as chatbots and LLM-assisted patient-clinician interaction summaries
  • Served as a contributor to leading AI standards including the NIST AI Risk Management Framework and the IEEE 7010-2020, Recommended Practice for Assessing the Impact of Autonomous and Intelligent Systems on Human Well-Being
     
Languages
  • English
  • Bulgarian

AWARDS AND RECOGNITION

  • VentureBeat Women in AI Awards Nominee, Women in AI Awards, (2020)
  • Kaggle Competition winner, CORD-19 research dataset ethical and social science considerations, (2019)
     

Publications

Seminars

  • Presenter, "Responsible AI Governance and Use," UN AI for Good - Law Track Conference, Stanford Law School, April 9, 2025
  • Speaker, "Red-teaming AI Systems in Healthcare," Health AI Partnership, December 18, 2024
  • Contributor, "Red Teaming Large Language Models for Healthcare," Machine Learning for Healthcare Conference pre-conference workshop, August 15, 2024

Prior Experience

Prior to joining DLA Piper, Bobbi was a Senior Trustworthy AI Fellow at Mozilla Foundation (2022 – 2024), Research Manager on Accenture's Responsible AI team (2019 – 2022), Research Fellow at Partnership on AI (2019 – 2020), Lead Editor for the Springer special issue Intersections of Artificial Intelligence and Community Well-Being (2018 – 2020), Senior Machine Learning Research Engineer at Samsung Research America (2014 – 2019), and Co-founder and CTO of HutGrip, a future-of-work technology startup (2012 – 2014). She also contributed to IEEE P7010-2020, Recommended Practice for Assessing the Impact of Autonomous and Intelligent Systems on Human Well-Being.

Memberships and Affiliations

  • Research Affiliate, Data & Society Research Institute, (2024 – Present)
  • Board Member, Happiness Alliance, AI Initiative (2019 – Present)
  • Research Fellow, Partnership on AI, (2019 – 2020)
  • Lead Guest Editor, Springer Special Issue: Intersections of Artificial Intelligence and Community Well-Being, (2018 – 2020)

Connect

Phone

+1 650 833 1515
(Work, Palo Alto)

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