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CTO Toolbox: 22 Resources For Building Great Engineering Teams

Billy Robins
April 09, 2024

In January, the Jellyfish team held our Company Kickoff in Boston. These annual kick-off meetings often lead me to reflect on what I’ve learned about the Engineering persona over the past 18 months, whether from customers, partners, colleagues or fantastic industry resources.

Before we get into it, here is some context on me and the company. 

For the past nine years, I’ve worked with a range of buyers: Customer Service (Zendesk), Product (Productboard), and now Engineering (Jellyfish). Unintentionally, this has been a great way to progress into increasingly sophisticated and complex buyers. 

Jellyfish sits at the intersection of two megatrends: Remote work and “every company is a software company.”  Executives want to understand how to make their entire company more effective. Historically, the research and development (R&D) function at software companies has been a black box, leading to confusion and occasionally distrust of the go-to-market (GTM) functions. Look no further than the Mckinsey vs Pragmatic Engineer intellectual battle royale on whether an engineer could and should be measured. 

It’s been a great 18 months to better understand the engineering function and how engineers work. Engineers are unique from product and customer service leaders. They are passionate about their work and motivated to solve complex problems. Additionally, they are very independent and looking to automate every task with technology. When it comes to software vendors, they are skeptical, especially when it comes to bold data claims.  

There are some common rules or laws that Engineering leaders know (that I’ve learned here at Jellyfish):

  • Goodhart’s Law. When a measure becomes a target, it ceases to be good. Engineers are brilliant and will likely take that path if there’s a way to cheat a system.
  • Brook’s Law. “Adding manpower to a late software project makes it later.” Best captured in “Mythical Man Month: Essays on Software Engineering.” by Fred Brooks.
  • Einstellung Effect. This psychological phenomenon refers to the tendency to approach a problem with a mindset that has worked in the past. The best engineers are creative, collaborative, and open-minded with problem-solving. 

I have learned a ton from our customers, calling out a few of them: Ian Lees, Andy Wright (Submittable), Scott Holland (Kaleris), Jamey Miller (OneTrust), Sidd Ramm.

I am sharing a list of resources that have helped my learning curve in engaging with engineers and engineering leaders. Here’s a list of resources (Substacks, Podcasts; Essays, etc) I’ve found incredibly useful (in no particular order). 

Substacks

Resources and Research

Podcasts

Slack Communities

  • Lenny Rachitsky. The first Product Manager at AirBnb and a savvy angel investor, Lenny has built an incredible community of people, resources and engagement.  Lenny also does an amazing job with essays and podcast.
  • Rands’ Leadership Slack. A very deep set of resources and active Slack community of Engineering leaders.

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