Engineering Leadership
Engineering Leadership

Engineering Leadership

by Gregor Ojstersek

Weekly Free / Paid

Navigate the path to CTO. Engineering Leadership by Gregor Ojstersek provides weekly, practical advice on scaling engineering teams, individual growth, and technical strategy.

About Engineering Leadership

Engineering Leadership is the 'playbook' for the modern CTO. Its weekly newsletter is famous for its 'Real World' case studiesโ€”sharing the specific hiring filters, promotion rubrics, and technical debt strategies that Gregor has used in his career. It's unique for its raw honesty about the 'lonely' seat of a CTO and its focus on the transition from 'coder' to 'strategist'. It is an essential read for anyone navigating the high-stakes world of startup leadership.

What Makes This Newsletter Unique

Mentorship at Scale. It feels less like a magazine and more like having a weekly 1-on-1 with a seasoned CTO.

Who Should Subscribe?

Engineers looking to move into management, and current leaders looking for a peer-perspective on scaling and operations.

Content Format

A sophisticated weekly email featuring one 'Deep Dive' guide and a list of 'Actionable Takeaways'.

Recent Newsletter Issues

View all archived issues
Apr 19, 2026

How an AI-Native Startup From SF Works and Builds Its Product

An insider's look into the workflows, tools, and culture powering a modern AI-first engineering team.

Apr 16, 2026

Become a Great Generalist or Extreme Specialist

Should you become a great generalist or an extreme specialist? One thing is clear: staying in the middle will result in fewer opportunities.

Apr 13, 2026

Code Review is the New Bottleneck For Engineering Teams

Building is now limited to how fast we are able to review the newly generated code. This is what to do in order to make it less of a bottleneck.

Pricing & Subscription Options

Premium Newsletter

  • Weekly emails
  • Unsubscribe anytime

Free weekly newsletter + Paid membership for full access and direct mentorship

View Pricing

Leave a Review

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Our Take: Pros & Cons

Pros

  • Transparent and honest advice from a current practitioner
  • Excellent for practical operational templates (rubrics, hiring)
  • Clear focus on the startup ecosystem

Cons

  • Higher density of 'career/management' vs 'technical' content
  • Requires a subscription for the full archive of templates

Frequently Asked Questions

Is it for junior devs?

While it can be inspiring, its content is primarily aimed at those in or aspiring to lead teams (Senior, Lead, Manager, CTO).

How often is Engineering Leadership published?

Engineering Leadership is published weekly.

Who writes Engineering Leadership?

Engineering Leadership is written by Gregor Ojstersek. Gregor Ojstersek is a seasoned CTO and VP of Engineering who has led several high-growth startups to successful outcomes. He is an active mentor and writer on the complexities of technical leadership.

About the Author: Gregor Ojstersek

G

Gregor Ojstersek

Gregor Ojstersek is a seasoned CTO and VP of Engineering who has led several high-growth startups to successful outcomes. He is an active mentor and writer on the complexities of technical leadership.

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