I was CTO of a startup from pre-seed stage ($0 raised, bootstrapping) thru Series A + B stages ($millions raised, scaling). I then promoted a senior engineer to the CTO role, around the time that we had ~20-30 engineers organized into sub-teams with engineering leads. As part of that, I ran an engineering management book club internally for the new CTO and engineering leads (which was also open to any engineers to join). I then published that reading list as a neatly organized blog post.

The team wrote web / SaaS / analytics software in Python and JavaScript, deployed on Linux + AWS, using lightweight planning tools like GitHub and Notion. It was also a fully distributed team long before the pandemic. Over time, the company (Parse.ly) gained hundreds of enterprise customers and established itself via profitable growth in a straightforward SaaS business model. In 2021, less than a year after this blog post was published, the company was acquired by one of the largest open web internet companies (Automattic, creators of WordPress.com).

"Managing software teams: the definitive reading list"

https://amontalenti.com/2020/11/28/definitive-reading-list

The blog post is organized into a few sections, each featuring a few relevant books:

- Management as a high-leverage activity

- Product marketing and product management

- Debugging dysfunctional product cultures

- The psychology of deep work

- Fully distributed teams

- Programmer mindset and philosophy

It's easy to skip around to find a good starting point or make your own (smaller) reading list. Hope that helps. Good luck!