Skylar PayneBuilding AI that actually works. Evaluation-driven development for engineering teams.https://skylarbpayne.com/Why Most Companies Fail to Build Strategic Assets with AIhttps://skylarbpayne.com/posts/ai-maturity-model/https://skylarbpayne.com/posts/ai-maturity-model/An AI Maturity ModelThu, 13 Feb 2025 00:00:00 GMTBuilding AI Products That Actually Work: A Hard-Won Guidehttps://skylarbpayne.com/posts/ai-product/https://skylarbpayne.com/posts/ai-product/Wed, 08 Jan 2025 00:00:00 GMTArtificial Intelligence for Businesshttps://skylarbpayne.com/posts/ai-for-business/https://skylarbpayne.com/posts/ai-for-business/A Strategic Guide to SuccessMon, 25 Aug 2025 00:00:00 GMTPatterns for AI Reliabilityhttps://skylarbpayne.com/posts/ai-reliability-patterns/https://skylarbpayne.com/posts/ai-reliability-patterns/Tue, 26 Aug 2025 00:00:00 GMTBringing Data Science Back to AI Engineeringhttps://skylarbpayne.com/posts/bringing-data-science-back-to-ai-engineering/https://skylarbpayne.com/posts/bringing-data-science-back-to-ai-engineering/Thu, 27 Nov 2025 00:00:00 GMTThe Answer is Always Evalshttps://skylarbpayne.com/posts/answer-always-evals/https://skylarbpayne.com/posts/answer-always-evals/Thu, 31 Jul 2025 00:00:00 GMTFinding True Northhttps://skylarbpayne.com/posts/data-driven-case-study-1/https://skylarbpayne.com/posts/data-driven-case-study-1/How LinkedIn''s Candidate Recommendation Project Changed My View of Data-Driven DevelopmentMon, 18 Nov 2024 00:00:00 GMTData is Wickedhttps://skylarbpayne.com/posts/data-is-wicked/https://skylarbpayne.com/posts/data-is-wicked/Fri, 30 Aug 2024 00:00:00 GMTBuilding an Experimentation Mindset in AI Teamshttps://skylarbpayne.com/posts/experimentation-mindset/https://skylarbpayne.com/posts/experimentation-mindset/A Leader''s GuideFri, 01 Nov 2024 00:00:00 GMT40% Better, 75% Fasterhttps://skylarbpayne.com/posts/frigade-ai-better-faster/https://skylarbpayne.com/posts/frigade-ai-better-faster/How Frigade Slashed Latency & Boosted User HelpfulnessTue, 20 May 2025 00:00:00 GMTFrom AI Ambitions to Action: A Mental Health Startuphttps://skylarbpayne.com/posts/healthrhythms-mood-score/https://skylarbpayne.com/posts/healthrhythms-mood-score/How HealthRhythms built their mood score systemThu, 10 Oct 2024 00:00:00 GMTThe Real Secret to Landing Your Dream Tech Jobhttps://skylarbpayne.com/posts/job-search-secrets/https://skylarbpayne.com/posts/job-search-secrets/It''s Not What You ThinkTue, 07 Jan 2025 00:00:00 GMTModernizing Data Infrastructure: A Mindstrong Case Studyhttps://skylarbpayne.com/posts/mindstrong-data-infra/https://skylarbpayne.com/posts/mindstrong-data-infra/Tue, 11 Oct 2022 00:00:00 GMTWhat Effective Leaders Get Righthttps://skylarbpayne.com/posts/most-important-job-leaders/https://skylarbpayne.com/posts/most-important-job-leaders/Thu, 14 Nov 2024 00:00:00 GMTA Practical Way to Evaluate Multi-Step and Multi-Turn Agentshttps://skylarbpayne.com/posts/multi-turn-eval/https://skylarbpayne.com/posts/multi-turn-eval/Mon, 01 Sep 2025 00:00:00 GMTQuality Assurance for AIhttps://skylarbpayne.com/posts/qa-ai/https://skylarbpayne.com/posts/qa-ai/Wed, 26 Mar 2025 00:00:00 GMTWhy RAG Is (Still) Not Deadhttps://skylarbpayne.com/posts/rag-not-dead/https://skylarbpayne.com/posts/rag-not-dead/The Enduring Value of Retrieval in the Era of Expanding Context WindowsSun, 06 Apr 2025 00:00:00 GMTAI Observability is Just Observabilityhttps://skylarbpayne.com/posts/ai-observability/https://skylarbpayne.com/posts/ai-observability/Mon, 17 Feb 2025 00:00:00 GMTWhy Your Team is Slowhttps://skylarbpayne.com/posts/why-your-team-is-slow/https://skylarbpayne.com/posts/why-your-team-is-slow/The Hidden Cost of Missing Business ContextTue, 29 Oct 2024 00:00:00 GMTTIL: Make AI Features Boring to Changehttps://skylarbpayne.com/posts/til-ai-call-bulkheads/https://skylarbpayne.com/posts/til-ai-call-bulkheads/AI features get scary to change when prompts, logs, evals, schema validation, fallbacks, and product code all blur together. Give the unreliable part one reliable interface so the next change has an obvious home.Sun, 10 May 2026 00:00:00 GMTThe Hidden Bottleneck in Knowledge Workhttps://skylarbpayne.com/posts/leadership-bandwidth/https://skylarbpayne.com/posts/leadership-bandwidth/Why Working Harder Isn''t WorkingSat, 19 Oct 2024 00:00:00 GMTEvals That Actually Get Usedhttps://skylarbpayne.com/posts/evals-that-get-used/https://skylarbpayne.com/posts/evals-that-get-used/A streamlined system for AI evaluation that closes the gap between seeing problems and fixing them.Tue, 17 Mar 2026 00:00:00 GMTBootstrapping AI Systems with Synthetic Data: 4 Approacheshttps://skylarbpayne.com/posts/synthetic-datagen/https://skylarbpayne.com/posts/synthetic-datagen/Sun, 23 Mar 2025 00:00:00 GMTGPT-5.4 in OpenClaw doesn’t suck. Your prompts do.https://skylarbpayne.com/posts/openclaw-gpt-5-4-vs-opus/https://skylarbpayne.com/posts/openclaw-gpt-5-4-vs-opus/Anthropic changed OpenClaw billing. We ran evals, tuned the bootstrap files, and GPT-5.4 got a lot better.Sat, 04 Apr 2026 00:00:00 GMTBuilding an Automated Email Reply Agent with Pydantic AIhttps://skylarbpayne.com/posts/pydantic-ai/https://skylarbpayne.com/posts/pydantic-ai/A Story of SimplificationFri, 03 Jan 2025 00:00:00 GMTThe Art of Iterative AI System Developmenthttps://skylarbpayne.com/posts/real-life-evals/https://skylarbpayne.com/posts/real-life-evals/A Practical Guide to Evaluation-Driven ImprovementSat, 08 Feb 2025 00:00:00 GMT5 Strategies for Improving Latency in AI Applicationshttps://skylarbpayne.com/posts/ai-latency/https://skylarbpayne.com/posts/ai-latency/Tue, 25 Feb 2025 00:00:00 GMTIf DSPy is So Great, Why Isn't Anyone Using It?https://skylarbpayne.com/posts/dspy-engineering-patterns/https://skylarbpayne.com/posts/dspy-engineering-patterns/Any sufficiently complicated AI system contains an ad hoc, informally-specified, bug-ridden implementation of half of DSPy.Sat, 21 Mar 2026 00:00:00 GMTThe Art of Interface Design: Making Good APIs that Scalehttps://skylarbpayne.com/posts/good-interfaces/https://skylarbpayne.com/posts/good-interfaces/Tue, 01 Apr 2025 00:00:00 GMT