author
Senior Applied Research Scientist
,
Snorkel AI
My general research interests are in machine learning, modeling richly structured graph data, and enhancing artificial intelligence systems with symbolic reasoning capabilities. I have developed models for a variety of applications, including computer vision, language modeling, social networks, demand forecasting, and recommender systems.
The latest from Charles
JudgmentBench: Comparing Rubric and Preference Evaluation for Quality Assessment
Two methodologies dominate current practices of benchmarking: rubric-based scoring evaluates items against predefined criteria, whereas comparative judgment elicits pairwise preferences between outputs. Although both methodologies are widely used, the choice between them is rarely justified. We release JudgmentBench, a benchmark of 30 real-world legal tasks, paired with 1,539 rubric scores and 1,530 pairwise preference judgments collected from practicing attorneys--including at major U.S. law firms--with substantial experience. The annotations constitute the first publicly available dataset in a high-expertise domain in which both supervision signals are elicited from the same experts on the same items. Using LLM-generated outputs at three constructed quality...
Research Paper
JudgmentBench: Comparing Rubric and Preference Evaluation for Quality Assessment
Two methodologies dominate current practices of benchmarking: rubric-based scoring evaluates items against predefined criteria, whereas comparative judgment elicits pairwise preferences between outputs. Although both methodologies are widely used, the choice between them is rarely justified. We release JudgmentBench, a benchmark of 30 real-world legal tasks, paired with 1,539 rubric scores and 1,530 pairwise preference judgments collected from practicing attorneys–including at…
RIFT: A Rubric Failure Mode Taxonomy and Automated Diagnostics
Rubric-based evaluation is widely used in LLM benchmarks and training pipelines for open-ended, less verifiable tasks. While prior work has demonstrated the effectiveness of rubrics using downstream signals such as reinforcement learning outcomes, there remains no principled way to diagnose rubric quality issues from such aggregated or downstream signals alone. To address this gap, we introduce RIFT: RubrIc Failure mode Taxonomy, a taxonomy for systematically characterizing failure modes in rubric composition and design. RIFT consists of eight failure modes organized into three high-level categories: Reliability Failures, Content Validity Failures, and Consequential Validity Failures. RIFT is developed using grounded theory by...
Research Paper
Accepted to ICLR Brazil 2026
RIFT: A Rubric Failure Mode Taxonomy and Automated Diagnostics
Rubric-based evaluation is widely used in LLM benchmarks and training pipelines for open-ended, less verifiable tasks. While prior work has demonstrated the effectiveness of rubrics using downstream signals such as reinforcement learning outcomes, there remains no principled way to diagnose rubric quality issues from such aggregated or downstream signals alone. To address this gap, we introduce RIFT: RubrIc Failure mode…
Benchmarking Agents in Insurance Underwriting Environments
As AI agents integrate into enterprise applications, their evaluation demands benchmarks that reflect the complexity of real-world operations. Instead, existing benchmarks overemphasize open-domains such as code, use narrow accuracy metrics, and lack authentic complexity. We present UNDERWRITE, an expert-first, multi-turn insurance underwriting benchmark designed in close collaboration with domain experts to capture real-world enterprise challenges. UNDERWRITE introduces critical realism factors often absent in current benchmarks: proprietary business knowledge, noisy tool interfaces, and imperfect simulated users requiring careful information gathering. Evaluating 13 frontier models, we uncover significant gaps between research lab performance and enterprise readiness: the most accurate models are not...
Research Paper
Accepted to CAIS 2026
Benchmarking Agents in Insurance Underwriting Environments
As AI agents integrate into enterprise applications, their evaluation demands benchmarks that reflect the complexity of real-world operations. Instead, existing benchmarks overemphasize open-domains such as code, use narrow accuracy metrics, and lack authentic complexity. We present UNDERWRITE, an expert-first, multi-turn insurance underwriting benchmark designed in close collaboration with domain experts to capture real-world enterprise challenges. UNDERWRITE introduces critical realism factors…
Blog
The science of rubric design
Part 3 of our rubric series explains the science of rubric design. We show why rubrics should be treated like models—structured, measured, and iterated—to maximize objective alignment and inter-rater agreement. Learn how to choose hierarchy and scale points, track agreement (IAA) and LLMAJ alignment, and refine with domain experts, with examples like PaperBench and HealthBench.
