
Roy Osherove
Chief Architect @ Verbit.ai
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Roy Osherove is a software architect and thought leader whose career spans writing The Art of Unit Testing, advising development teams, and teaching leadership principles directly from software trenches. He’s also author of Elastic Leadership: Growing Self-Organizing Teams, a framework for adapting your style as teams evolve. His specialty: building systems, teams, and tools that survive real world mess — and sharing where they break first.
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Cursor: Notes, Tips & Tricks from a Hardcore User (2025 Edition)
Cursor is one of those tools that seems “nice” until you realize it can completely change how you work — if you actually learn its hidden commands, rules and other hidden features. Over the past 2 years, I’ve used Cursor as my main editor for real production work: onboarding new devs, refactoring ugly legacy repos, and working on full features and bug fixes.
The amount of actual MANUL code lines Ive written in the past year is less than 100.
This talk is a practical, no-fluff tour of Cursor’s most useful commands, the weird edge cases, when we change models for different tasks, and the little prompts that make a big difference when you’re deep in the zone. Think of it as “things I wish someone told me before I started yelling at my AI assistant.”
Outline:
• My daily workflow: refactors, context jumping, debugging, onboarding
• The commands that save hours — and the ones that waste them
• Advanced commands , Spec-Kit
• Common pitfalls, fixes, and a few command recipes that actually work
A developer's introduction to web3
What makes web3 development different? What does a basic decentralized app architecture look like? What skills can you dive into in this world? All this and more will be shown by Roy Osherove.
RepoSwarm: Giving AI Agents Architecture Context Across All Your Repos
If you’ve got 30+ repos, you know the pain: every “AI code tool” you try feels blind outside its little sandbox. RepoSwarm , a new open source tool, started as an experiment to fix that — a way to give AI agents full context across multiple repos, docs, and readmes. I’ll share what we built, how it actually works under the hood, and what surprised us when agents started reasoning across projects (both the good and the frustrating parts that still aren't great).
Topics:
* Why AI tools are blind in multi-repo setups
• RepoSwarm’s architecture: Temporal, Prompting, scraping, embedding, permissions
• What happens when agents “see” your whole org
• Practical takeaways for dev teams
Mapping a company AI Tool Stack in 2025
Everyone talks about building an “AI stack,” but few people show what that actually looks like when you’ve got researchers, developers, and non-technical folks across multiple teams, all trying to use it at the same time. I’ll walk through how I mapped our AI stack — what goes where, who uses what, and how we avoid burning weeks integrating shiny tools that don’t talk to each other. It’s part architecture, part survival guide, from the point of view of a chief architect.
Topics:
* What an “AI stack” actually means in practice
• My mapping process: dev, research, and non-tech zones
• Where tools clash (and how to keep the peace)
• Lessons from shipping this setup in production
The Enterprise DevOps Challenge
DevOps is the implementation of continuous delivery and agile concepts across the organization, focusing on pipelines as the main building blocks for delivery value internally and to the customer.
But getting to that state is complicated because it requires several facets of work: People, process and tools.
In large organizations ,we have the added complexity of :
" Multiple dependencies and sub systems
" Multiple teams, groups, business units with competing interests
" Varying degrees of agility, culture, tools, technologies and processes
" Security, compliance and policy gates
In this talk we will discuss main patterns and anti patterns for adopting and implementing DevOps pipelines throughout the organization.
The Coaching Leader & Architect
In this session Roy looks at one of the biggest problems in technical work today: lack of training for tech leads and architects in skills such as leadership, people skills and becoming change agents in organizations. Roy will also cover the ideas of Elastic Leadership and how they can apply in many different software work situations.
Things covered will include, among others:
- How should you measure your success in your role?
- What to do in difficult situations such as conflicts at work with peers
- How to grow the people on your team to gain more skills
- When to break the rules
- When to make the rules
- When to coach, and how
You can find more info on this at 5whys.com
Feature Flags, Source control Branching Myths, strategies, dragons and tactics
In this talk Roy presents several strategies for managing source control branching when working with multiple teams and their dependencies. We will also cover pros and cons of various strategies, relating to CI/CD.
Creating a QA/DEV Collaborative Testing Strategy
In the new software world, Testers are expected to know more and more automation and rely less and less about manual testing strategies.
In an agile driven, devops world, testers are also expected to collaborate and work on testing related activities during development, and not after.
In this talk we will discuss what such a process might look like in real life, what meetings, documents or artifacts are created by DEV and QA relating to tests,
and what strategies we can use to decide what types of tests to apply to a specific feature.
All this, in a collaborative manner along with QA & developers.
If we can make this work, we will all be much more productive.
recommended as a keynote.
Lies, Damned Lies, Metrics and KPIs
They say that "you get what you measure", and we've all seen it happen. "We need to get the coverage up!" followed by people frantically writing tests that might not test anything.
Coverage is up. Quality? not so much.
So what metrics can we use to drive the things we believe in?
In this session, Roy Osherove covers leading and lagging indicators we can use in software delivery, including some major anti-patterns to watch out for, and how each metric could drive our team towards a bleaker, or brighter future.
The Pipeline Driven Organization
Why are some organizations able to implement true continuous delivery, and others are endlessly struggling and striking out on the path there?
I this talk we will introduce the idea of pipeline-driven processes - and how those are different from "we just have a few Jenkins jobs lying around".
By delegating Tactical day to day IT related decisions to pipelines, instead of letting humans make them, we can slowly achieve true continuous delivery.
In a pipeline-driven world, testers need to learn new skills (coding, automation, coaching). Ops need to learn new skills (coaching, infra as code, testing). Security folks need to learn new skills (coaching, testing, automation and coding, ops). Devs need to learn new skills (coaching, testing, ops, security). Compliance need to learn new skills (automation, testing, coaching).
Everyone is affected.
Pipeline driven organizations pull us out of our silos and into more collaboration. It can be really painful if we don't know what to expect.
In this talk we will discuss what such a process might look like in real life, what types of possible collaborations can exist, and what challenges we face making it happen.
Test Driven Development with Modern Javascript
Javascript has evolved into an ecosystem with many choices and multiple paradigms of programming. In this session Roy will show how test driven development can still work and be applied to backend and frontend situations using ES2015 as well as the core concepts of TDD and why it can be helpful in your day to day job
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