Latest
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“Vibe hacking” signals seismic shift for engineering leaders
Blackhat hackers have an addition to their armoury. Here’s how engineering leaders can safeguard their systems and stay on high alert.
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Is GitHub’s coding agent your newest junior dev?
GitHub’s new coding agent has some perks, but is still showing signs of significant growing pains. What are the current pain points?
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Why most developers hate their tech stack
Outdated tech stacks are a top reason for developers to quit.
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Software engineering with GenAI
A look at how AI coding tools are reshaping software engineering, how teams are adapting, and what remains unchanged in the development process.
Editor’s picks
October 15 & 16, 2025
Agendas for New York events are live! 🙌
Essential reading
How to build an effective technical strategy
Building a tech strategy requires a lot of moving parts. Learn about what routes to take and whether decisions should be top-down.
On our Technical Direction playlist
Modernizing legacy systems: A technical strategy for evolving monoliths into modern architectures at HelloFresh
Gain insights into transforming legacy systems into scalable architectures, with practical strategies for balancing stability, managing technical debt, and enabling growth opportunities at HelloFresh.
Technical Vision vs. Technical Strategy: The difference and why it matters
Jonathan Maltz digs into the nuts and bolts of setting a successful technical strategy. Startin by talking about the difference between technical vision and technical strategy.
How to implement platform engineering at scale
In this webinar, we’ll hear from enterprise engineering leaders who’ve overcome cultural barriers and team silos, and successfully adopted platform engineering practices in their orgs.
Good technical debt
Jon Thornton discusses how this framework was used to rapidly build and ship Squarespace’s Email Campaigns product in less than 15 months. Along the way, you’ll get several practical guidelines for how tech debt can supercharge your technical investments.
Creating, defining, and refining an effective tech strategy
Having a defined tech strategy creates alignment and keeps everyone on the same page. So how can you ensure yours is most effective? Panelists Anna Shipman, Randy Shoup, Papanii Nene Okai, Nimisha Asthagiri and Anand Mariappan share their tips.
Agendas for New York events are live!
Lineup includes Addy Osmani, Kevin Goldsmith, Robin Bonatesta, and more…
New York • October 15 & 16, 2025
More about Technical Direction
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Managing technical risk
Understanding the motivations behind an engineer’s desire to affect your tech stack
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Conversations you need to have before moving from monoliths to microservices
Are you making the move for the right reasons?
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Embracing simplicity in your engineering team
The prevention of inherent, project-lifecycle-induced, and self-inflicted complexity
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Gathering requirements: techniques for building a solid backlog
Leverage domain knowledge to establish a foundation for your projects
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Achieving speed and quality without sacrifice in engineering
Combining curiosity and focus to unite two traditionally opposing forces
Top Technical Direction videos
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Do the hard stuff
Polina Giralt talks about how some of the most impactful technical work is about unwinding a humungous mess. This talk is about lessons learned over my career about executing challenging projects. The types of projects with politics, drama, tech debt, or past failed attempts. How do we know if the project is worth doing? Why has it failed before? Who’s blocking it? How do we know when to cut our losses and pause or cancel the project?
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Everything is a migration: Putting evolutionary architecture into practice
Jason Blanchard explores the idea that we can model and de-risk change by thinking of everything as a migration from a current state to a desired state and what that means for our architecture and teams
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Terraform practices to enable infrastructure scaling
Hila Fish covers useful best practices, pitfalls to avoid and major obstacles to anticipate so that you can scale them across many teams, avoid refactoring, and get a flying start now — AND optimize for the future.
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Technical Vision vs. Technical Strategy: The difference and why it matters
Jonathan Maltz digs into the nuts and bolts of setting a successful technical strategy. Startin by talking about the difference between technical vision and technical strategy.
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The (updated) story of why we migrate to gRPC and how we go about it
Matthias Grüter addresses technical discussions of advanced gRPC concepts such as interceptors, load balancing, and traffic management and how they are essential in large distributed systems.
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Good technical debt
Jon Thornton discusses how this framework was used to rapidly build and ship Squarespace’s Email Campaigns product in less than 15 months. Along the way, you’ll get several practical guidelines for how tech debt can supercharge your technical investments.
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Strategies for cloud migration
Constantinos Svendinoglou talks about the Data Group at Squarespace which has been on a transformational journey to migrate our systems to the cloud. At the beginning of 2022, we were running entirely on our own hardware; but by the end of 2023 we expect to be 100% cloud native. This talk will cover the strategy, tactics and execution that went into effect to make the migration to being cloud native over possible.
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Building koi pond: simulating millions of slack clients
Join Maude Lemaire for a roller coaster ride of a story and a thrilling live demo of what Slack’s load testing systems can do!