The Curious Engineer

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A guide to scaling product & engineering teams from $0 to past $100M ARR.

Engineering management / careersSoftware / engineering practiceEssays / personal

’20’21’22’23’24’25’26
Posts
190 from 6 Apr 2020 to 14 Oct 2026
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monthly (20 in the last year)
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personal blog
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2026 15

  1. Management in the Age of AI
  2. Hiring Breakpoints
  3. Defensive Driving For Your Career
  4. Book the Meeting Before You Need It
  5. The Same Side of the Table
  6. The Big Management Lie: Overpromising
  7. The Best Prioritization Is No Prioritization
  8. What I’d Tell My Team About Competition
  9. Riding Technology Waves
  10. Don’t Stack Weaknesses
  11. What It’s Like to IPO
  12. High Amplitude Disagreeableness
  13. Management In The Age Of AI
  14. Avoiding a Culture of Emergencies
  15. The Most Important Teams in Tech

2025 27

  1. 2025: Another SaaSy Year In Review
  2. Advice For Individual Contributors
  3. The Compensation Commandments
  4. Own A Graph
  5. The Two Jobs of a CPO
  6. Leveling Up Teams Fast and Slow
  7. Specialization Is For Insects
  8. How to Compete in SaaS
  9. No Pain, No Gain
  10. You Know What To Do
  11. You Have Too Many Metrics
  12. Naming Software Teams
  13. We Tried That
  14. Your Manager Is Not Your Best Friend
  15. AI Makes Bad Managers
  16. Setting Startup Policies
  17. Leading From The Front
  18. The Precise Language Of Good Management
  19. First Principles Problems, Secondhand Solutions
  20. Managing People You Can't Fire
  21. Tips For Better Interactions
  22. Blameful Post-Mortems
  23. Delegating Complex Tasks
  24. Mutually Assured Mediocrity
  25. This Is How You're Eroding Accountability
  26. Management Mantras
  27. Bottleneck Dirty Webs

2024 25

  1. 2024: A SaaSy Year In Review
  2. Problem Driven Development
  3. Networking For People Who Don't Network
  4. A Practical Guide to Executive Presence: Earning Respect
  5. Don't Act Differently After You Give Notice
  6. Questions for Orienting Your SaaS Strategy
  7. Stop Trying To Replace Your SaaS Products With AI
  8. Harvesting, Fishing, Panning for Gold
  9. Standardizing
  10. Fighting With Your Boss
  11. I Like Dumb Plans
  12. Don't Try To Step-Function Everyone All At Once
  13. Unspoken Startup Folk Wisdom
  14. Managing High Performers
  15. Platform Support
  16. Consistent Traits of the Best Startup Scalers
  17. Have Concerns And Commit
  18. Advice That I Can't Get Out of My Head
  19. Getting Things Done In A Chaotic Environment
  20. A Technology Leader's Non-Technical Reading List
  21. Engineers Are Not A Commodity
  22. Hiring Experienced Executives At Your Startup
  23. How To Fix Broken Teams
  24. Performance Reviews Matter
  25. This Is the Person Selling Your Product

2023 31

  1. 2023: A SaaSy Year In Review
  2. Practical Ways To Increase Product Velocity
  3. Hidden in Plain Sight: Unraveling Big Problems Disguised as Small Unrelated Issues
  4. Weak Power Gets Tested
  5. Your Small Imprecise Ask Is a Big Waste of Their Time
  6. Startup Make-Believe
  7. Thoughts on Product-Market Fit
  8. Fair but Unequal
  9. (People on) Nice Teams Finish Last
  10. Dont Bring Me Problems, Bring Me Solutions
  11. New Hires: Learn How The System Breaks
  12. When To Hire Your First PM
  13. Moving From IC to Engineering Manager
  14. The Future of Remote Work
  15. Stop Making People Make Up Their Mind
  16. Twitter, Threads, and the Great Social Implosion
  17. On Achieving Goals
  18. SaaSy Questions #1: Compensation Heuristics
  19. How To Be An Engineer That PMs Don't Hate
  20. A Practical Guide to Executive Presence
  21. Finding and Fostering Great Product Sense
  22. Starting Software Teams: Avoiding Big Mistakes
  23. Rooting Out Red Tape At Your Startup
  24. DEI For Dummies
  25. Numbers To Know For Managing (Software Teams)
  26. How to Be a PM That Engineers Don't Hate
  27. Culture Viruses
  28. How Acquirers See Your Company
  29. Selling to the Enterprise: Challenging SaaS Incumbents
  30. Management Debt
  31. The Pendulum Swings: How To Respond To Tech's Downturn

2022 26

  1. Enterprise Retention Means Solving Hard Problems
  2. Management Lessons From Elon's Twitter
  3. Traits You Can Change, and Traits You Can't
  4. Negativity Bias, I Love You But You're Bringing Me Down
  5. How to Run a Department
  6. The SaaSy Guide to Hiring
  7. Why Figma is Special
  8. Build Your Career on Dirty Work
  9. How to Give Bad News
  10. How to Be a Senior Leader
  11. Notes and Errata (from previous posts)
  12. Small Performance Cues
  13. Good Managers Write Good
  14. Low Context - Software's Silent Killer
  15. Value Sell Recruiting
  16. How to Improve Your Gross Margins
  17. Battlefield Product Management
  18. Don't Build Useless Features
  19. The Most Important Performance Management Rule For Software Engineers
  20. Ways to Expand Your SaaS Business
  21. Working Across Departments
  22. Selling to the Enterprise: Be Enterprise-Ready
  23. Stop Writing Great Runbooks
  24. The Swiss Army Product Management Team
  25. Working with Integrity
  26. Complexity Debt

2021 25

  1. Your Head of Product and Your CEO
  2. Managers Should Optimize Job Satisfaction, Not Happiness
  3. Debugging My Work Health
  4. Behold the Power of Small Data
  5. Where to Innovate, Where to Imitate
  6. Give People Something To Look At
  7. Stop Looking For Mentors
  8. Managing Engineering Managers: A Primer
  9. Selling to the Enterprise: Crafting Product Narratives
  10. What To Do When Your Team Quits
  11. Goals, Problems, Solutions
  12. Simple Ways To Be Less Divisive
  13. Check Up On Your Team's Kids
  14. Things 10x People Do
  15. Competitive Analysis For Product Engineers
  16. The Intangible Skills You Can't Interview For
  17. A Year Of SaaSiness
  18. How I Read Product Manager Resumes
  19. Low Priority Issues + Time = Relationship Killer
  20. Machine Learning Won't Save Your Startup
  21. The Most Valuable Question When Interviewing Managers
  22. Reframing Imposter Syndrome
  23. Avoiding The One Step Back
  24. Have Bad Days and Let Others Have Them Too
  25. Proactive vs. Reactive Teams

2020 41

  1. Data: Use, With Caution
  2. How Satisfied Are You With Your Job, On a Scale of 1-10?
  3. Unlimited is a Ponzi Scheme
  4. Selling to the Enterprise #4: Which Competitors Matter?
  5. Maximizing the Value of Reference Calls
  6. Selling to the Enterprise #3: Expand the Playing Field
  7. Three Types of Management Problems
  8. A Blessing and a Curse
  9. Unforced Errors
  10. My Startup Reading List
  11. Management Scrutiny
  12. 7 Reasons Your Growth Startup Is Hiring Too Junior
  13. Soft Skills for Managers
  14. Selling to the Enterprise #2: Avoid Saying No
  15. Optimize Onboarding
  16. Post Series: Selling to the Enterprise
  17. The 3 Minute Guide to One-on-Ones
  18. Consistent Caliber Teams
  19. Transparency is the Key to Accountability
  20. Grow Skills With Work, Not Extracurriculars
  21. The Rogue Wave of Enterprise SaaS
  22. Why It's Easier to Manage 4 People Than It Is to Manage 1 Person
  23. Manager Superpower Series #2: Optimism
  24. Don't Create Chaos
  25. Stop Blocking Things at the Last Minute
  26. The Hardest Part of Working at a Growth Startup
  27. Promote Imperfect People
  28. The Goldilocks Management Structure
  29. Stop Sabotaging Your Career With Short Stints
  30. A VP Product's Reading List
  31. Advice to New Managers: Don't Joke About Firing People
  32. Picking Your Tech Stack For Dummies (and the future)
  33. The Perils of Startup Engineering
  34. My Superpower: Waking Up Early
  35. I'm Building a Startup – Is This Normal?
  36. Everything I’ve Learned About Running Meetings Comes From Not Wanting to Be There
  37. Product Management Career Ladder Archive
  38. Engineering Career Ladder Archive
  39. Writing Performance Reviews 101
  40. Product Roadmap Detours
  41. Creating Good Process