Escaping Technical Purgatory

Engineering Evolved

Why Mid-Sized Companies Are Stuck (And How to Break Free)

You've achieved product-market fit. You're generating real revenue. You have 200-1000 employees and a tech team of 20-150 engineers. You're not a startup anymore—but you're also not Google.

And you're stuck in hell.

The VP of Engineering reads all the right blogs, follows all the thought leaders, and decides to implement microservices like Netflix. Six months later, deployments take longer, bugs multiply, engineers threaten to quit, and leadership is asking why you just spent half a million dollars to make things worse.

This isn't incompetence. This is the reality of being in the missing middle—too big for startup playbooks, too small for enterprise frameworks.

In this episode, host Tom Barber breaks down:

• The 6 types of debt suffocating your company: code, documentation, process, architecture, testing, and knowledge debt
• Why startup methodologies fail at scale (and destroy your company faster)
• Why enterprise playbooks will kill you just as quickly (change advisory boards, anyone?)
• How to build your own playbook with three critical questions every leader must ask

Stop trying to copy Spotify. Stop implementing frameworks designed for 10,000 employees. Start building systems that match your actual reality.

Perfect for: CTOs, VPs of Engineering, and technical leaders at mid-sized companies who are tired of advice that doesn't fit their world.

• (00:00) - Intro
• (01:01) - Titles
• (01:44) - Techincal Purgatory
• (05:37) - Why Startup Methodologies Fail At Scale
• (12:25) - The Importance Of Documentation And Ownership
• (22:14) - The Pitfalls Of Enterprise Engineering Playbooks
• (30:45) - Building Your Own Playbook