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Technical deep-dives, tutorials, and insights on AI experimentation and optimization.

tutorialsuncategorizedproductresearchthought leadershipengineering
tutorials4 min read

Stage 3: Adversarial Probe, Not Optional

An exploit probe tests your assertions, not the agent. Winnow's QA tab runs N deterministic strategies against every published task's assertions — if any strategy slips through, the task is held until you tighten.

Aaron Gasperi
tutorials3 min read

Block-Mode HIL: A Queue, Not a Channel

When a customer-facing agent emits request_human_input(...) in block mode, somebody needs to answer in minutes — not in the next Slack thread. Winnow's HIL queue lives where reviewers already work, expands inline, and resumes the agent the moment the answer lands.

Aaron Gasperi
uncategorized3 min read

Calibration Center — cross-suite judge triage on Winnow

Winnow Team
tutorials5 min read

The Harness Pill: Decomposing a Scorecard Without Leaving the Page

Most regressions in agent evals don't come from the prompt — they come from the scaffold that runs the prompt. Winnow's Scorecard Overview tab now regroups itself when you flip the Arm / Model / Harness toggle. The Harness pill is the load-bearing one.

Aaron Gasperi
tutorials3 min read

Multi-Agent Cost: Make the Dominant Agent Visible

When a manager-researcher-writer scaffold spends $24 a week instead of $17, the question isn't 'which arm' — it's 'which agent'. Winnow's B7 agent rollup turns per-span agent_id tags into one cross-trace cost table and one per-trace span tree, both colored by the same agent palette.

Aaron Gasperi
product2 min read

Run the Probe From the QA Tab

The exploit-probe QA tab now carries a Run probe now button — capture the probe spec inline, POST to the existing route, and watch the new result row land without leaving the page.

Aaron Gasperi
tutorials3 min read

Scaffolds: Versioning the Whole Agent, Not Just the Prompt

A prompt is one ingredient. A scaffold is the whole recipe — prompts plus tools plus model config — pinned to one immutable hash that a trace can point back to. Winnow now ships a scaffold history page so you can audit which recipe shipped when.

Aaron Gasperi
tutorials4 min read

Smart Suggestions: Three Next-Actions, Not Eleven Dashboards

Eleven eval capabilities surface eleven data points. A suite home that shows all eleven at once is a stress chart, not a workplace. Winnow's P6 smart suggestions strip is the prioritization layer that turns those eleven into up to three actionable nudges — and renders nothing when none of them fire.

Aaron Gasperi
tutorials4 min read

Frontier vs Regression: A Two-Word Vocabulary for Release Gates

Not every failing eval should block a release. A two-bucket task classification — frontier (informational) vs regression (release-blocking) — lets your CI gate the things that matter without burying the things that are still aspirational.

Aaron Gasperi
tutorials5 min read

When the Judge Drifts: Calibration Monitoring for LLM Evaluators

LLM judges are not stationary. Models, rubrics, and human labellers all shift. Winnow's calibration baselines catch the moment your judge stops agreeing with humans, before the dashboard lies to you.

Aaron Gasperi
tutorials3 min read

Oracle vs Expected Output: Two Fields That Look the Same and Aren't

An oracle solution and an expected-output blurb both describe what a good answer looks like — but only one is a concrete answer the platform can auto-grade against. Why Winnow's dataset row editor now carries both, side by side.

Aaron Gasperi
tutorials3 min read

Five Judges in One Call: Rubric-Itemized Evaluation in Winnow

Replacing N independent LLM-judge criteria with one rubric collapses N HTTP round-trips per trial into one — same per-item κ, ~Nx cost savings, no behavioral regression.

Aaron Gasperi
product5 min read

Onboarding bridges: drop Winnow into your stack without rewriting your call sites

Winnow now supports 23 sources at beta. Swap one import. Backfill from a JSONL export. Or point your OpenTelemetry exporter at us. Pick the path that costs you the least.

Aaron Gasperi
research13 min read

How many times should your model answer?

A full-lifecycle answer: instrument every sample, build the statistical prior, validate on your traffic, and jointly budget training, inference, and k under one spend ceiling.

Aaron Gasperi
research6 min read

Why does your frontier model lose on cost per correct answer?

Roberts et al. just published a scaling law that reframes which model you should run. Here is why that matters to anyone running LLM applications in production, and what Winnow ships to make it actionable.

Aaron Gasperi
tutorials6 min read

How to A/B Test Your LLM: A Complete Guide

Standard A/B testing breaks down with non-deterministic models. Learn how to run statistically rigorous experiments on LLM outputs using mSPRT and the Winnow SDK.

Aaron Gasperi
thought leadership7 min read

Winnow vs. Manual Evaluation: Why Eyeballing LLM Outputs Doesn't Scale

The hidden costs of manual LLM evaluation and how automated, statistically rigorous testing replaces gut checks with evidence.

Aaron Gasperi
engineering8 min read

Understanding mSPRT: Sequential Testing for AI Experiments

A technical deep-dive into mixture Sequential Probability Ratio Tests -- the statistical engine behind continuous experiment monitoring in Winnow.

Aaron Gasperi
tutorials8 min read

Feature Flags for AI Applications: A Practical Guide

How to use feature flags to safely manage model rollouts, prompt versioning, and gradual deployments in production AI pipelines.

Aaron Gasperi
product8 min read

Introducing the Winnow Optimization Agent

Meet the autonomous agent that observes, proposes, and executes optimizations across your AI pipeline -- with 5 levels of autonomy and built-in safety controls.

Aaron Gasperi

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