JW Tech Strategies
I help growing companies identify when to scale organizational structure, infrastructure, and security – and when scaling would destroy them. After 25 years of leading technology teams and writing extensively about scaling features, I’ve learned that timing isn’t everything. It’s the only thing.
The Two Ways Companies Destroy Themselves
Scaling Too Late looks like this: A startup that worked beautifully at 50 people starts cracking at 200. Leadership insists on preserving the “flat culture” that made them successful, eliminating management layers and resisting process. They call it empowerment. Their best engineers call it chaos—right before they leave. By the time leadership acknowledges the problem, they’ve lost institutional knowledge that took years to build.
Scaling Too Early looks like this: A company with 20 employees builds infrastructure designed for 2,000. They implement enterprise security frameworks before they have enterprise revenue. They hire directors before they need directors. The overhead consumes resources that should fuel growth. They’ve built a mansion when they needed a foundation.
Both failures share the same root cause: leadership that couldn’t recognize where they actually were versus where they wanted to be.
Signs You’re Scaling Too Late
– Your “flat organization” has informal hierarchies that everyone knows but no one acknowledges
– Senior engineers are drowning in coordination work instead of engineering work
– You’ve lost more than one key person who cited “lack of growth opportunity”
– Decisions that used to take a conversation now take a month of meetings
Your best people are training their replacements at other companies
Signs You’re Scaling Too Early
– You have more process than product
– Your infrastructure costs are growing faster than your revenue
– You’ve implemented compliance frameworks your customers don’t require
– You have managers managing managers before you have teams that need management
– Your technical architecture could handle 100x your current load, but you can’t make payroll for six months
Signs You’re in the Danger Zone
– Leadership disagrees on which problem you have
– You’re solving last year’s scaling challenge instead of next year’s
– Your technical decisions and organizational decisions are made by different people who don’t talk to each other
The Scaling Equation
Most business books tell you what to do. They assume you know when to do it.
That assumption destroys companies.
I wrote The Scaling Equation series because I kept watching smart leaders make smart decisions at exactly the wrong moment. The books follow Sarah Brennan, a DevOps leader who walks into organizations that look successful on the surface but are weeks away from catastrophic failure. The warning signs are always there. They’re always ignored.
The Accountability Gap: Why Flat Organizations Fail at Scale examines what happens when companies refuse to scale their organizational structure alongside their growth. GlobalTech’s leadership eliminated management layers to preserve their startup culture. Within eighteen months, they’d lost their best engineers, botched their most critical product launch, and destroyed decades of institutional knowledge—all while insisting the “culture” was stronger than ever.
The Goldilocks Principle (forthcoming in 2026) explores the opposite failure: companies that build for scale before they’ve earned scale. They implement enterprise solutions for startup problems, burning resources and creating complexity that actively prevents the growth they’re preparing for.
The DevOps Assessment Guide provides the diagnostic methodology I use in every engagement. Assessment must precede implementation. You cannot fix what you haven’t accurately diagnosed, and most organizations are treating symptoms while the disease spreads.
How We Can Work Together
Every company’s scaling challenge is different—but the patterns are remarkably consistent. Whether you need a second opinion before a critical decision, an honest assessment of where you actually are, or a partner to navigate the transition with you, the work starts in the same place: figuring out your timing.
Pattern Recognition at the Inflection Point — Architecture and infrastructure reviews when growth is outpacing what you’ve built. Organizational design conversations when your team structure no longer fits your company size. Technology due diligence before acquisitions, investments, or major platform bets. Board-level translation of technical scaling risks into business language.
Diagnostic Assessment Using the DevOps Assessment Framework — A concentrated evaluation of your systems, infrastructure, security posture, and organizational structure against your actual growth trajectory. You walk away with a written diagnostic report, a 90-day action plan, a 12-month strategic roadmap, and an executive briefing document—all built around the question that matters most: Are you scaling at the right time, in the right places, in the right order?
Ongoing Strategic Partnership — For organizations actively navigating the shift from one stage of growth to the next. Scaling sequence planning, team development, security and compliance implementation, vendor management, and continuous pattern recognition as conditions change. Designed for growing companies between 50–500 employees who have outgrown one stage but haven’t yet built for the next.
The engagement scales to what you need—a single conversation, a half-day workshop, or an ongoing partnership. The goal is always the same: help you see where you actually are so you can make the right decision at the right time.
About
I’m Josh, the founder of JW Tech Strategies and a Marine Corps Veteran.
I’ve spent over 25 years in technology leadership – building infrastructure, leading engineering teams, and watching organizations succeed and fail based on decisions that seemed minor at the time. My career has taken me through wireless technologies, gaming, aerospace, cybersecurity, and multi-media/marketing – always in roles where I was responsible for making systems work and scale.
What I’ve learned is that technical problems are rarely just technical. The code, the infrastructure, the security posture – these are symptoms. The disease is almost always organizational: leadership that can’t see where they actually are, teams structured for a company size that no longer exists, processes designed for problems that have evolved.
I started writing about these patterns because I kept having the same conversations. Smart leaders, capable teams, companies with real market opportunity – all making the same timing mistakes I’d seen destroy previous organizations. The books in The Scaling Equation series aren’t abstract theory. They’re the patterns I’ve witnessed and repeatedly, documented so that others might recognize the warning signs before it’s too late.
Published Work
The Accountability Gap: Why Flat Organizations Fail at Scale
Sarah Brennan was the DevOps Manager who kept GlobalTech running. For eight years, she built the systems, developed the talent, and solved the problems that executives never saw. Then leadership decided to “flatten” the organization and eliminate management layers to preserve their startup culture.
They called it empowerment. Sarah called it chaos.
Within eighteen months, the company lost its best engineers, botched its most critical product launch, and destroyed decades of institutional knowledge—all while leadership insisted the “culture” was stronger than ever. Sarah documented every warning sign. She proposed solutions. She fought for her team.
They fired her anyway.
The Accountability Gap is a business fable about the most common—and most ignored—failure mode in growing companies: the refusal to scale organizational structure alongside business growth. Through Sarah’s story at GlobalTech, you’ll witness how flat organizations that work brilliantly at 50 people collapse catastrophically at 500.
Book One of The Scaling Equation Series – available on Amazon
The DevOps Assessment Guide: A Practical Framework for DevOps Leaders
You’ve just stepped into a DevOps leadership role. Now what?
You inherited a complex environment with pipelines you didn’t build, processes you didn’t design, and technical debt no one warned you about. Leadership expects results. Your team is watching. And somewhere in your organization, there’s a problem waiting to explode.
The pressure is real—but you don’t have to figure it out alone.
THE DEVOPS ASSESSMENT GUIDE is the diagnostic manual every DevOps leader needs but few have. Unlike other DevOps books that teach you what DevOps is or how to implement it, this book answers the question that matters most in your first 90 days:
What have I actually inherited, and how do I systematically evaluate it?
Assessment must precede implementation. – available on Amazon
Let’s Figure Out Your Timing
Whether you’re worried you’re moving too fast, too slow, or can’t tell which – let’s talk.