Kurt Overberg is a senior technologist and engineering executive with 25+ years of experience building products that scale – from co-creating foundational web infrastructure in the 90s to leading 26-person engineering organizations at Pluralsight to applying LLMs to real business problems today. He works with companies that need CTO-level thinking without the full-time overhead.
Some examples
Guided a $200M+ acquisition through rigorous technical evaluation
A company needed an independent technical assessment before acquiring a real-time bidding engine in the online advertising space. The stakes were high — the wrong call meant hundreds of millions at risk.
8
architectures evaluated
WHAT WAS DONE
Led the migration to a modern hosting provider, dramatically improving management tooling and observability while cutting infrastructure spend by over three-quarters.
Migrated 400+ customer websites with 75% cost savings
A client was running hundreds of customer sites on an aging, expiring hosting platform with poor observability and high operating costs. A migration was necessary — and risky.
WHAT WAS DONE
Led the migration to a modern hosting provider, dramatically improving management tooling and observability while cutting infrastructure spend by over three-quarters.
Turned weeks of manual data work into a minutes-long automated process
An education client had multiple team members spending weeks manually moving data into their analytics warehouse. The process was error-prone, slow, and didn’t scale.
WHAT WAS DONE
Engineered customized Python automation to ingest and deliver educational data into a PostgreSQL data warehouse, eliminating the manual process entirely.
NOTABLE BACKGROUND
Plualsight – Senior Director of Engineering
BzzAgent – Founder and CTO
Harvard Innovation Lab – Mentor
Open Market – FastCGI / Payments Flow
