Skylar Payne
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The Answer is Always Evals
I gave a guest lecture in Hamel and Shreya’s AI Evals for Engineers and PMs course (my slides).
It was a ton of fun, and I really apprecate the opportunity to share my…
Jul 31, 2025
40% Better, 75% Faster
How Frigade Slashed Latency & Boosted User Helpfulness
ai
rag
evals
Frigade faced a critical challenge: users were complaining about their AI assistant’s performance.
May 20, 2025
Why RAG Is (Still) Not Dead
The Enduring Value of Retrieval in the Era of Expanding Context Windows
ai
rag
Every time a new Large Language Model debuts, the headlines follow a predictable pattern: “New Model with 1M Token Context!” Then come the hot takes: “RAG is Dead!” “No More…
Apr 6, 2025
The Art of Interface Design: Making Good APIs that Scale
engineering
As I’ve led engineering and data science teams across companies like Google, LinkedIn, and now as VP of Engineering & Data Science, I’ve observed a pattern:
teams that…
Apr 1, 2025
Quality Assurance for AI
ai
flywheel
evaluation
qa
Traditional software quality assurance relies on predictable, deterministic behavior—the same input always produces the same output. But AI systems fundamentally break this…
Mar 26, 2025
Bootstrapping AI Systems with Synthetic Data: 4 Approaches
ai
flywheel
synthetic-data
Your CEO is asking why the AI isn’t working, but you’re caught in the classic catch-22: you need user data to improve the AI, but you need working AI to attract users.
Mar 23, 2025
5 Strategies for Improving Latency in AI Applications
ai
Your CEO just asked why customers are churning from your AI feature. You know the AI works, most of the time. But there’s that nagging feeling every time you watch users…
Feb 25, 2025
AI Observability is Just Observability
ai
observability
Your CEO just asked why the AI gave that customer a hallucinated response yesterday. You stare at your expensive AI observability dashboard, scroll through dozens of…
Feb 17, 2025
Why Most Companies Fail to Build Strategic Assets with AI
An AI Maturity Model
ai
evals
flywheel
Evaluate your AI Maturity today with a free assessment!
Click Here to Get Started
Feb 13, 2025
The Art of Iterative AI System Development
A Practical Guide to Evaluation-Driven Improvement
ai
evals
Improving AI systems is hard. Unlike traditional software where you can often directly observe and fix bugs, AI systems present unique challenges:
Feb 8, 2025
Building AI Products That Actually Work: A Hard-Won Guide
ai
Your CEO just asked why the AI feature isn’t driving the growth you promised. That familiar sinking feeling washes over you as you realize you have no systematic way to…
Jan 8, 2025
The Real Secret to Landing Your Dream Tech Job
It’s Not What You Think
job-search,networking
After a decade in tech, including years at LinkedIn working on their job matching algorithms and now serving as VP of Engineering & Data Science, I’ve seen thousands of…
Jan 7, 2025
Building an Automated Email Reply Agent with Pydantic AI
A Story of Simplification
agents
ai
tools
After years of leading machine learning teams at companies like Google and LinkedIn, I’ve re-learned the same lesson over and over again: start simple and slowly add…
Jan 3, 2025
Finding True North
How LinkedIn’s Candidate Recommendation Project Changed My View of Data-Driven Development
data
leadership
experimentation
Your CEO just asked why the AI feature isn’t driving the growth you promised. That familiar sinking feeling?
I’ve lived it.
Nov 18, 2024
What Effective Leaders Get Right
leadership
Most organizations struggle with process improvement. They either move too slowly, optimize the wrong things, or fail to create sustainable change. After years of leading…
Nov 14, 2024
Building an Experimentation Mindset in AI Teams
A Leader’s Guide
data
leadership
experimentation
Your team keeps saying they need to “experiment more” with AI, but you’re not sure what that means or how to measure success. Sound familiar? That sinking feeling when your…
Nov 1, 2024
Why Your Team is Slow
The Hidden Cost of Missing Business Context
leadership
Over my career leading engineering and data science teams — from regulated industries to early-stage startups to large enterprises — I’ve consistently seen one pattern…
Oct 29, 2024
The Hidden Bottleneck in Knowledge Work
Why Working Harder Isn’t Working
leadership
It’s 11 PM on a Sunday. You’re putting the finishing touches on a critical project, convinced that
this
extra push will finally get it over the line. Sound familiar?
Oct 19, 2024
From AI Ambitions to Action: A Mental Health Startup’s Journey
data,case-study
“We need AI to measure patient mood.”
Oct 10, 2024
Data is Wicked
data
Picture this: A data scientist spends hours configuring YAML files, debugging pipeline errors, and switching between five different tool UIs just to test a simple feature…
Aug 30, 2024
Modernizing Data Infrastructure: A Mindstrong Case Study
data,case-study
When data infrastructure struggles to keep pace with business needs, the impact ripples throughout an organization. As Lead Machine Learning Engineer at Mindstrong, I…
Oct 11, 2022
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