Awesome CTO

— Hello, my name is Dima and I’m a CTO

— (chorus) Welcome, Dima

A curated and opinionated list of resources for Chief Technology Officers and VP R&D, with the emphasis on startups and hyper-growth companies.

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Contents

• CTO Position
• Hiring
• People management
• Career growth
• Project management
• Handbooks
• Development process
• Architecture
• Technologies
• Data
• Startups
• Due Diligence
• Money / Finance
• Related stuff
• Product
• Marketing
• Books
• More links

CTO Position

• The Different CTO Roles - Werner Vogels (Amazon CTO)
• Is it required to be a developer to become a CTO? (Quora)
• Three Golden Rules to Finding a CTO
• Becoming a CTO
• VP Engineering vs CTO - Fred Wilson (Union Square Ventures)
• What makes for a successful CEO and CTO relationship in a startup? (Quora)
• #define CTO - Greg Brockman (Stripe CTO)
• How my role as CTO has changed as we’ve grown to 100 engineers
• Your first 90 days as CTO or VP Engineering - Will Larson
• How to spend your first 30 days in a new senior-level role
• The difference between a CTO and a VP Engineering
• Evolution of my role as a founder CTO, Year 4 Update, Year 5 Update - Miguel Carranza

Hiring

• The Guerrilla Guide to Interviewing - Joel Spolsky (StackOverflow co-founder)
• The Joel Test: 12 Steps to Better Code - Joel Spolsky
• Why Can’t Programmers.. Program? - Jeff Atwood (StackOverflow co-founder)
• We Hire the Best, Just Like Everyone Else - Jeff Atwood
• Getting the Interview Phone Screen Right - Jeff Atwood
• Engineering interview process at Stripe (Quora)
• Improving Our Engineering Interview Process (Foursquare)
• Hitting the High Notes - Joel Spolsky
• Top 10 System Design Interview Questions - (HackerNoon)
• How To Hire World-Class Engineers (angel.co)
• Trouble hiring senior engineers? It’s probably you
• The Real 11 Reasons I Don’t Hire You - Charity Majors
• How to Interview at Amazon
• Lessons from Keith Rabois: How to Interview an Executive
• Lessons from Keith Rabois: How to Become a Magnet for Talent
• GitLab Talent Acquisition Framework
• Visualizing Tech Company Layoffs in 2022

People Management

• The mythical 10x programmer - Salvatore Sanfilippo (author of Redis)
• The Engineer/Manager Pendulum - Charity Majors
• Maker’s Schedule, Manager’s Schedule - Paul Graham (Y Combinator)
• Software Engineering at Google
• Google re:Work
• 44 Engineering Management Lessons (correct link to non-violent communication for lesson 34)
• The Secret To Discussing Pay With Employees
• Awesome Leading and Managing (Github)
• A Review Process - Cap Watkins
• 12 manager readmes from top tech companies
• Predictable Delivery
• How people rise up to EVP level in big organizations (Quora)
• Should I Become a Manager? - Cap Watkins
• How to fail as a new engineering manager
• Design Patterns for Managing Up
• A Tactical Guide to Managing Up
• Engineering Management (Github)
• On-boarding Software Engineers
• Hold Your Team Accountable
• The Manager FAQ
• The Power of Performance Reviews
• Performance reviews are coming up - Gergely Orosz
• Principles of Engineering Management
• Draw The Owl and Other Company Values You Didn’t Know You Should Have
• A MANAGER’S BILL OF RESPONSIBILITIES (AND RIGHTS)
• After Being A Manager, Can I Be Happy As A Cog?
• Increment: Teams
• Hacking team communications
• How to build a startup engineering team
• Hug your manager
• Lessons from Keith Rabois: How to be an Effective Executive
• How Context Switching Sabotages Your Productivity
• 10,000 Hours with Reid Hoffman: What I Learned
• 7 Ways to Set Up a New Hire for Success
• How to get promoted
• Individuals matter
• Mandate Levels
• 10 ideas for building great culture in a distributed (remote) team
• Adapting to Endure / Crisis management - Sequoia
• Mochary Method Curriculum - Matt Mochary
• Meetings for an effective eng organization - Will Larson
• The One Key to Dealing with Senior Executives: Answer the Question!
• Step by step guide to building high performing teams
• Cycle times - Andrew Bosworth

Career growth

• Career Growth Frameworks in Software Engineering: A Review
• Software Engineers Growth framework
• Software Engineering Ladders (GitHub)
• Awesome Engineering Ladders (GitHub)
• Reverse Interview
  • The Reverse Interview: How To Choose Your Next Company
  • Reverse Interviewing — How to interview a company as well as they interview you
  • Reverse Interview Questions (GitHub)

Project management

• Evidence Based Scheduling - Joel Spolsky (StackOverflow co-founder)
• How Big Tech Runs Tech Projects and the Curious Absence of Scrum - Gergely Orosz
• The Secret to a Great Planning Process — Lessons from Airbnb and Eventbrite
• What TPMs Do and What Software Engineers Can Learn From Them - Gergely Orosz
• How to Scope a New Feature
• Measuring an engineering organization - Will Larson

Handbooks

• The Atlassian Team Playbook
• Valve Employee Handbook
• Basecamp Employee Handbook
• GitLab Team Handbook
• How HashiCorp Works

Development process

• Scrum / Agile
  • Introduction to Scrum for Managers and Executives
  • Writing User Stories, Examples and Templates In Agile Methodologies
• CI / CD
  • What are the fundamental principles of continuous integration?
  • The Product Managers’ Guide to Continuous Delivery and DevOps
• Git
  • Comparing Git workflows
  • A successful Git branching model
  • Alternative: Trunk Based Development (focused on DevOps and CI/CD)
• Tech debt
  • Why You Should Learn to Stop Worrying and Love Technical Debt
  • It’s Time to Rethink Technical Debt Management
• Crisis
  • How to Write a Postmortem
  • List of Post-mortems (GitHub)
  • Startup Lessons Learned - Five Whys - Eric Ries (creator of the Lean Startup)
  • On Call Rotations: How Best to Wake Devs Up in the Middle of the Night
  • Testing in Production, the safe way
• Error handling
  • When life gives you lemons, write better error messages

Architecture

• Twelve-Factor App
• Reactive Manifesto
• An introduction to distributed systems - Kyle Kingsbury (aphyr, author of Jepsen)
• Microservices – Please, don’t (also: HackerNews discussion)
• GitHub CTO – Biggest architectural mistake was going full microservice (also: HackerNews discussion)
• The Death of Microservice Madness in 2018
• Shrinking microservices to functions
• Design patterns for microservices
• Serverless architecture (Quora)
  • Serverless framework
• Best Practices for Designing a Pragmatic RESTful API
• 10 Modern Software Over-Engineering Mistakes
• How I Write Tests
• Lambda Architecture
• Awesome Scalability (GitHub)
• The Single Most Important Internal Email in the History of Amazon
• Build Your Own X (GitHub)
• Accentuate the negative: making the non-perfect decision. Technical decision making

Technologies

• General
  • Developer Roadmaps (GitHub)
  • Coding Interview University (GitHub)
  • Big-O explained in plain English
• Javascript
  • JS: The Right Way
  • Frontend developer handbook 2019
• Big scale
  • What is CAP Theorem? (Quora)
  • CAP Theorem: Revisited
• Security
  • Awesome Security (GitHub)
  • SaaS CTO Security Checklist
• Search
  • Open Guide to Search Engineering (GitHub)
• Cloud
  • Open Guide to Amazon Web Services (GitHub)
  • Amazon AWS in Plain English
  • Microsoft Azure in Plain English
  • Google Cloud Services for the AWS expert
• Pricing
  • Awesome Billing (GitHub)
  • Awesome PriceOps (GitHub)

Data

• NoSQL Databases: a Survey and Decision Guidance
• Evolutionary Database Design (Martin Fowler)
• Database Migrations Done Right
• A reference guide for fintech & small-data engineering
• Building a data team at a mid-stage startup: a short story
• DataOps
• Databases in 2022: A Year in Review
• Data Science
  • Building a data science team
  • Managing Data Science Teams
  • How to Structure a Data Science Team
• Machine Learning
  • Awesome Machine Learning (GitHub)
  • Best resources of everyday ML learning (Quora)
  • Machine Learning Crash Course: with TensorFlow APIs (Google)
  • Deep Learning For Coders
  • Awesome Production Machine Learning (GitHub)
  • Weapons of Math Destruction

Startups

• What are the things startups have to get right? (Quora)
• 85 Things I learned being a CEO
• What’s the Second Job of a Startup CEO?
• Things I will tell my kids if they become entrepreneurs
• What do VCs really look for when making investments? (Quora)
• As an employee of a startup, how do you know when to quit? (Quora)
• Pitch deck collection from VC funded startups
• YC’s Series A Diligence Checklist
• Startup Playbook - Sam Altman
• Y Combinator Startup Class
• Lean Canvas + Miro template
• Open Source Pitch Deck Templates for Figma
• List of startups that had successful pivots (GitHub)

Due Diligence

• Technology Due Diligence Checklist
• Technical Due Diligence Questions (GitHub)
• IT Department Tech Due Diligence Checklist
• A Guide to Surviving Tech Due Diligence

Money / Finance

• Startups
  • IPOs and Beyond: A Guide to Exit Options for Companies
  • What would a CTO equity be for a small startup? (Quora)
  • Options vs Cash
  • How To Invest In Startups - Sam Altman
  • A Guide to Seed Fundraising
  • Startup Economics equity calculator
  • Option grants at seed
  • Joining the new startup, with a handsome stock option allocation - Gergely Orosz
  • Equity 101 for Software Engineers at Big Tech and Startups - Gergely Orosz
• Big companies
  • Financial Planning & Analysis @ GitLab
  • Framework for balancing and budgeting engineering resourcing
  • Negotiate the right deal with suppliers
  • Strategic Procurements 10 Commandments for Managing the Buying Process

Related stuff

• Knowledge-Sharing Architects As An Alternative to Coding Architects
• Ten Rules for Negotiating a Job Offer (also: HackerNews discussion)
• Salary Negotiation: Make More Money, Be More Valued
• What are best practices of experienced programmers? (Quora)
• Falsehoods Programmers Believe About Names
• 2016 European Software Development Salary Survey (O’Reilly)
• DevOps: Bringing development and operations together (Atlassian)
• How to Prepare a Talk
• Undervalued Software Engineering Skills: Writing Well - Gergely Orosz
• The Pyramid Principle
• Senior Engineer’s Checklist
• How to Use OpenAPI and Swagger for Documentation

Product

• What Makes a Great Product Manager
• If You Don’t Think You Need a VP of Product…
• Red Oceans: How to Find Profitable Startup Ideas
• Product North Star Metric
• What distinguishes the Top 1% of product managers from the Top 10%? - (Quora)
• How to Hire a Product Manager
• The Secrets Of Creative Thinking
• StellarPeers - Product Management Interviews
• Product vs. Feature Teams
• Most Startups Should Be Deer Hunters
• Shape Up: Stop Running in Circles and Ship Work that Matters
• How to Write Your First Strategic Roadmap
• Execution at Facebook
• 8 Product Hurdles Every Founder Must Clear
• The Top 10 Deliverables of Product Managers
• Product Manager Career Ladders - Lenny Rachitsky
• Awesome Product Management (GitHub)
• Awesome Product Manager (GitHub)

Marketing

• Developer Marketing Guide
• Top Resources for Startup Marketing and PR
• SaaS Email Marketing Handbook
• How today’s fastest growing B2B businesses found their first ten customers

Books

• Epic CTO Reading List
• The Mythical Man-Month
• Startup CTO’s Handbook

More links

• Awesome Falsehood (GitHub)
• Engineering blogs (GitHub)
• Awesome Awesomeness (GitHub)
• Awesome.re (GitHub)
• Chief Technology Officer vs Coder Thinker Organizer (GitHub)
• Senior Software Engineer
• Socal CTO
• Curated list of CTO resources (GitHub)
• Awesome CTO Resources (GitHub)
• Free Tools for Developers
• NfX - The Founder Library
• foundr - Advices from founders
• The Leadership Library for Engineers
• Rands Leadership Slack
• Engineering Managers Slack
• CTO Framework
• CTO Insights Podcast

Other

• Awesome CEO (GitHub)
• Awesome TPM (GitHub)

License