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Sean McKenna

@seanmckenna

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Finance domain expert and AI model trainer specializing in LLM evaluation for investment research.

United States

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What I'm looking for

I seek roles leveraging finance domain expertise and AI model training to improve LLM accuracy and workflow integration, ideally at firms valuing rigorous validation and collaborative ML/product teams.

I am a finance domain expert with 22 years of combined sell-side and buy-side experience, now specializing in AI model training and evaluation for investment and research workflows.

I design question–answer datasets, perform LLM evaluations on finance-specific tasks like DCF and comp analysis, and audit AI outputs for accuracy, compliance, and interpretability.

My background includes senior research roles at hedge funds where I built and stress-tested complex financial models, integrated alternative data and sentiment, and produced investment memoranda used by portfolio managers.

I combine hands-on financial modeling and Python automation with experience in annotation platforms, prompt-testing tools, and ML alignment to help firms integrate reliable generative AI into buy-side and sell-side research processes.

Experience

Work history, roles, and key accomplishments

Current

AI Training Consultant

Current

Independent Consultant

Jan 2025 - Present (10 months)

Provide domain-expert guidance for AI projects focused on financial analysis, designing Q&A datasets and evaluating model performance on DCF, comp analysis, and earnings interpretation to improve alignment with professional workflows.

Prompt Engineering Data Annotation Financial Modeling Python

Senior Research Analyst

Orso Partners

Oct 2020 - Feb 2025 (4 years 4 months)

Developed and presented long/short investment theses, built and stress-tested 3-statement and DCF models, and integrated alternative-data and sentiment signals into valuation frameworks used by portfolio managers.

Financial Modeling Alternative Data Python Data Pipelines Investment Research Due Diligence

Senior Research Analyst

Lyon Street Capital

Oct 2013 - Oct 2020 (7 years)

Led fundamental research on small- and mid-cap equities, built custom screening and ranking models with Python and Excel automation, and sourced alternative datasets to strengthen investment signals.

Fundamental Research Python Screening Alternative Data Due Diligence Investment Recommendations

Equity Research Analyst

Various Boutiques

Jan 2001 - Jan 2013 (12 years)

Conducted sell-side equity research across U.S. and global equities, building financial models, publishing initiation and earnings reports, and delivering sector coverage to institutional clients.

Sell Side Research Financial Modeling Report Writing Sectors Client Communication Valuation