## Overview Twilio Segment, a customer data platform company, developed a novel LLM evaluation system called "LLM-as-Judge" to assess and improve their generative AI-powered audience building feature. The core product challenge was to enable marketers to create sophisticated customer audiences through simple natural language prompts rather than navigating complex user interfaces. This case study provides valuable insights into how to build robust evaluation frameworks for production LLM systems, particularly when dealing with outputs that can have multiple valid representations. The CustomerAI audiences feature allows marketers to describe an audience in natural language (e.g., "Customers who have purchased at least 1 time") and have the system automatically generate the corresponding query logic. According to Segment, customers using this feature experienced a 3x improvement in median time-to-audience creation and a 95% feature retention rate when the audience generation works on the first attempt—highlighting the business-critical importance of getting the LLM outputs right. ## The Core Evaluation Challenge The fundamental challenge Segment faced was how to evaluate a generative AI system when there can be an unbounded set of "right answers." Behind the Segment UI, audience definitions are compiled into Abstract Syntax Trees (ASTs), which are tree-like data structures representing code structure similar to JSON objects. The same audience logic can be expressed in multiple semantically equivalent ways. For example, "Customers who have purchased at least 1 time" could also be correctly expressed as "Customers who have purchased more than 0 times but less than 2 times." Traditional evaluation approaches using exact matching or rule-based systems would fail in this context because they cannot account for semantic equivalence. This is a common challenge in LLMOps for code generation, SQL generation, and any domain where outputs have flexible structure but need to maintain semantic correctness. ## LLM-as-Judge Architecture Segment adopted the "LLM-as-Judge" paradigm, which uses a separate LLM (the "judge") to evaluate, compare, and score prompt-output pairs against ground truth examples. This approach draws on recent research including JudgeLM, Prometheus, Generative Judge for Evaluating Alignment, and particularly the LLM-SQL-Solver paper which focuses on determining SQL equivalence—directly relevant to AST evaluation. The architecture consists of several interconnected components working together: - **Real World AST Input**: Ground truth ASTs provided by customers through the UI, serving as the reference for evaluation - **LLM Question Generator Agent**: Generates synthetic natural language prompts based on the ground truth ASTs - **LLM AST Generator Agent**: Takes generated prompts and produces ASTs using LLMs (this is the actual production system being evaluated) - **LLM Judge Agent**: Evaluates the generated AST against the ground truth AST and provides a score This multi-agent approach demonstrates a sophisticated understanding of evaluation requirements in production LLM systems. ## Synthetic Evaluation Data Generation One of the most interesting aspects of this case study is the synthetic evaluation data generation approach. Segment had a large dataset of ground truth ASTs from their UI, but these ASTs lacked corresponding natural language prompts since they were created through the UI rather than natural language input. To solve this, they built an "LLM Question Generator Agent" that takes a ground truth AST and generates a plausible natural language prompt that would produce that AST. This is essentially running the generation process in reverse—extracting prompts from outputs rather than outputs from prompts. The synthetic prompts are then fed into the AST Generator Agent, and the resulting AST is compared against the original ground truth by the LLM Judge. This approach to synthetic data generation is valuable for organizations that have structured data but need to create evaluation sets for natural language interfaces. It enables the creation of large-scale evaluation datasets without requiring expensive human annotation. ## Scoring and Chain of Thought Segment discovered several practical lessons about using LLMs for evaluation that are broadly applicable: **Discrete Scoring Scales**: LLMs struggle with continuous scores. When asked to provide scores from 0 to 100, models tend to output only discrete values like 0 and 100. Segment addressed this by using a discrete 1-5 scale, with 1 being "very bad" and 5 being "perfect." This made results more interpretable and reliable. **Chain of Thought (CoT) Reasoning**: Implementing Chain of Thought prompting for the judge model improved alignment with human evaluators from approximately 89% to 92%. CoT allows the model to explain its reasoning, which serves dual purposes: it improves the quality of judgments and makes it easier for engineers to understand and debug the evaluation process. This transparency is crucial for building trust in automated evaluation systems. ## Model Comparison and Results The evaluation framework enabled systematic model comparison, which is one of the primary use cases for any LLMOps evaluation system. Segment tested multiple models for the AST Generator Agent: - The Claude model scored 4.02 out of 5.0 - GPT-4-32k-0613 achieved the highest score of 4.55 out of 5.0 - Notably, there was remarkable similarity in scores between the 8K and 32K context length versions of GPT-4, demonstrating stability across context window sizes For the Judge model itself, Segment used OpenAI's GPT-4. Interestingly, they found that using other strong models like Claude 3 Opus as the judge produced similar scores to GPT-4, suggesting good alignment between different frontier models when used as evaluators. The overall LLM Judge Evaluation system achieved over 90% alignment with human evaluation for ASTs, which is a strong result that justified moving to production with this automated evaluation approach. ## LLMOps Applications The evaluation framework serves multiple LLMOps purposes beyond one-time model selection: - **Model Selection**: Systematically comparing different models (GPT-4 vs Claude) with quantitative metrics - **Prompt Optimization**: Testing prompt changes and ensuring new prompts perform better than existing ones - **RAG and Persistent Memory**: Evaluating the impact of adding components like vector databases on end-user quality - **Architecture Decisions**: Comparing single-stage vs multi-stage LLM approaches Having baseline scores enables continuous iteration and optimization. As Segment explores adding persistent memory via RAG, adopting new models, or changing prompting strategies, they can compare new scores against baselines to quantify impact. ## Privacy and Responsible AI Considerations Segment emphasizes their AI principles of being Transparent, Responsible, and Accountable. They reference a "Generative Audiences Nutrition Facts Label" that documents how data is used for this feature. This is an important aspect of production LLM systems that is often overlooked in technical discussions but is critical for customer trust and regulatory compliance. ## Future Directions Segment outlined several planned optimizations that reflect ongoing LLMOps challenges: - Improving correlation between LLM Judge and human scores to ensure better alignment with human judgment - Orchestrating different agents using frameworks such as AutoGen for better coordination and efficiency - Applying LLM Judge methodology to different CustomerAI use cases across various domains ## Critical Assessment While this case study provides valuable insights, there are some considerations worth noting. The 90% alignment with human evaluation sounds impressive, but the remaining 10% of cases where the automated judge disagrees with humans could represent edge cases that are disproportionately important. The case study does not detail how they handle or investigate these disagreement cases. Additionally, using an LLM to evaluate another LLM creates potential blind spots—both models may share similar failure modes that neither would catch. Segment's finding that different frontier models (GPT-4, Claude 3 Opus) produce similar judgments could be interpreted positively (agreement indicates correctness) or negatively (shared biases in training). The synthetic data generation approach, while clever, may introduce distribution shift if the LLM-generated prompts don't accurately reflect how real users phrase their requests. This could lead to optimizing for a different distribution than production traffic. Despite these caveats, the LLM-as-Judge approach represents a practical and scalable solution to a real production challenge, and Segment's willingness to share specific metrics (90% alignment, 4.55/5.0 scores, 89% to 92% improvement with CoT) provides useful benchmarks for others implementing similar systems.