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Engineering Evolved
Tom Barber
11 episodes
2 days ago
Where business meets innovation and technology drives transformation. Engineering Evolved is the podcast for leaders navigating the forgotten ground between startup chaos and enterprise bureaucracy. If you're building and scaling teams at organizations in the middle — where startup rules no longer apply and enterprise playbooks are far too large — this show is for you. Hosted by Tom Barber, each episode explores the real challenges facing today's engineering leaders: scaling systems without breaking them, building high-performing teams, aligning engineering strategy with business goals, and making technical decisions that drive measurable impact. Whether you're a Director of Engineering, VP of Technology, CTO, or an IC engineer stepping into leadership, you'll find practical insights drawn from real-world experience — not theoretical frameworks that only work on whiteboards. Topics include: Scaling engineering teams and systems for growth Building effective engineering culture Bridging the gap between technical and business strategy Leadership tactics that actually work in the messy middle Making architectural decisions with limited resources Navigating organizational complexity Engineering Evolved — guiding today's leaders through the evolution of engineering. New episodes drop weekly. Subscribe now and join the conversation about what it really takes to lead engineering in the modern era.
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Technology
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All content for Engineering Evolved is the property of Tom Barber and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Where business meets innovation and technology drives transformation. Engineering Evolved is the podcast for leaders navigating the forgotten ground between startup chaos and enterprise bureaucracy. If you're building and scaling teams at organizations in the middle — where startup rules no longer apply and enterprise playbooks are far too large — this show is for you. Hosted by Tom Barber, each episode explores the real challenges facing today's engineering leaders: scaling systems without breaking them, building high-performing teams, aligning engineering strategy with business goals, and making technical decisions that drive measurable impact. Whether you're a Director of Engineering, VP of Technology, CTO, or an IC engineer stepping into leadership, you'll find practical insights drawn from real-world experience — not theoretical frameworks that only work on whiteboards. Topics include: Scaling engineering teams and systems for growth Building effective engineering culture Bridging the gap between technical and business strategy Leadership tactics that actually work in the messy middle Making architectural decisions with limited resources Navigating organizational complexity Engineering Evolved — guiding today's leaders through the evolution of engineering. New episodes drop weekly. Subscribe now and join the conversation about what it really takes to lead engineering in the modern era.
Show more...
Technology
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Escaping Technical Purgatory
Engineering Evolved
39 minutes
1 week ago
Escaping Technical Purgatory

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
Engineering Evolved
Where business meets innovation and technology drives transformation. Engineering Evolved is the podcast for leaders navigating the forgotten ground between startup chaos and enterprise bureaucracy. If you're building and scaling teams at organizations in the middle — where startup rules no longer apply and enterprise playbooks are far too large — this show is for you. Hosted by Tom Barber, each episode explores the real challenges facing today's engineering leaders: scaling systems without breaking them, building high-performing teams, aligning engineering strategy with business goals, and making technical decisions that drive measurable impact. Whether you're a Director of Engineering, VP of Technology, CTO, or an IC engineer stepping into leadership, you'll find practical insights drawn from real-world experience — not theoretical frameworks that only work on whiteboards. Topics include: Scaling engineering teams and systems for growth Building effective engineering culture Bridging the gap between technical and business strategy Leadership tactics that actually work in the messy middle Making architectural decisions with limited resources Navigating organizational complexity Engineering Evolved — guiding today's leaders through the evolution of engineering. New episodes drop weekly. Subscribe now and join the conversation about what it really takes to lead engineering in the modern era.