A. Dsouza
Publications
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 iteratively annotating rubrics drawn from five diverse benchmarks spanning general instruction following, code generation, creative writing, and expert-level deep research, until no new failure modes are identified. We evaluate the consistency of the taxonomy by measuring agreement among independent human annotators, observing fair agreement overall (87% pairwise agreement and 0.64 average Cohen's kappa). Finally, to support scalable diagnosis, we propose automated rubric quality metrics and show that they align with human failure-mode annotations, achieving up to 0.86 F1.
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 the most efficient, models hallucinate domain knowledge despite tool access, and pass^k results show a 20% drop in performance. The results from UNDERWRITE demonstrate that expert involvement in benchmark design is essential for realistic agent evaluation, common agentic frameworks exhibit brittleness that skews performance reporting, and hallucination detection in specialized domains demands compositional approaches. Our work provides insights for developing benchmarks that better align with enterprise deployment requirements.