/ Research & Ideas

Simon
Obstbaum.

Simon
Obstbaum.

Simon
Obstbaum.

Researcher. Entrepreneur.

Researcher. Entrepreneur.

Researcher. Entrepreneur.

Software engineering researcher and serial entrepreneur. Since 2020, I’ve focused on how teams can measure and improve developer productivity, including the practical impact of AI.

Software engineering researcher and serial entrepreneur. Since 2020, I’ve focused on how teams can measure and improve developer productivity, including the practical impact of AI.

Previously, I served as CTO at Crunchyroll and founded YOPESO, growing engineering organizations across the US, Europe, and Asia.

Previously, I served as CTO at Crunchyroll and founded YOPESO, growing engineering organizations across the US, Europe, and Asia.

Talks & media.

Talks & media.

Simon Obstbaum speaking at Nationalmuseum in Stockholm

The Great Engineering Reshuffle — Nationalmuseum, Stockholm

I presented The Great Engineering Reshuffle at Proxify Talks at Nationalmuseum in Stockholm on October 19, 2026.

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adidas Tech Summit 2026 venue in Zaragoza

Keynote at adidas Tech Summit 2026 — Zaragoza

I delivered one of two external keynotes—alongside Gene Kim—at the 10th adidas Tech Summit in Zaragoza on October 1, 2026.

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From Vibes to Metrics: Why Evals Are Hard — AI Native DevCon London 2026

At AI Native DevCon London 2026, Rob Willoughby and I explained why output-only evals miss how AI agents work—and how trajectory evals and instrumentation make performance measurable.

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Simon Obstbaum speaking on an AWS Startups panel at Meeting of the Minds in Singapore

AWS Meeting of the Minds, Singapore: What actually works when building sustainable AI companies?

With global AI investments projected to reach $1.8 trillion by 2030, the panel explored the fine line between innovation and short-term hype.


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The 20% Truth: AI’s Real Impact on Developer Productivity

In this episode of Fractional, I discuss what the data really says about AI’s impact on developer productivity.

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Code with Jason podcast artwork

Ghost Engineers with Yegor Denisov-Blanch and Simon Obstbaum

The conversation explores how different developers contribute varying value, how life circumstances impact work motivation.

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Roundtable on Engineering Excellence

A roundtable on engineering excellence, generative AI, and data-backed approaches to measuring software engineering productivity.

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Simon Obstbaum speaking at the DPE Summit

Stanford Research: Measuring Software Engineering Productivity

Effective decision-making in software organizations relies on good data: you can’t improve what you don’t measure.

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McKinsey Roundtable: Software Engineering Excellence

An invitation-only McKinsey roundtable on practical approaches to software engineering productivity.

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