Embarking on a journey as a first-time Chief Technology Officer (CTO) in a startup can be both exhilarating and daunting. The role of a CTO varies significantly depending on the size and nature of the organization, and as such, the resources that will be most beneficial can differ. Here are some recommended readings and resources tailored to different scenarios:

For Tech Leads in Small Teams

• “Staff Engineer’s Path” by Tanya Reilly: Suitable if the role involves leading a small, single-team engineering organization. This book offers insights relevant to staff engineers and those leading them​​.

For Leading Large Organizations

• “An Elegant Puzzle” by Will Larson: Recommended for those who are overseeing large organizations where hands-on technical work is less feasible. This book focuses on building effective structures and cultures within an organization​.

For New Managers

• “Becoming an Effective Software Engineering Manager” by James Stanier and “Engineering Management for the Rest of Us” by Sarah Drasner: These books are ideal for individuals transitioning from engineering roles to managing a team of engineers​

General Material

• Gergely Orosz’s Pragmatic Engineer Newsletter: Provides templates and processes which are helpful for those new to the CTO role. This resource can serve as an excellent starting point for creating organizational documents and processes​.

Comprehensive Reading List

• “Managing Software Teams: The Definitive Reading List”: Published on amontalenti.com, this blog post by a former startup CTO offers a comprehensive reading list. It covers management, product marketing, dealing with dysfunctional cultures, deep work, managing distributed teams, and the programmer mindset​.

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