A CTO’s Perspective: How Legend Influences Strategic Technical Decisions

As a CTO, my job isn’t just about tech—it’s about making smart, strategic calls that shape where the business goes next. Let me walk you through how I approach technical decisions with long-term impact in mind, from budgeting to hiring and beyond.

Why Expertise Isn’t Optional in Tech Leadership

Good tech leadership is hard to find. It’s like hunting for rare coins: you want pieces that hold value, not just shiny objects. In my experience, the best engineers aren’t just technically sharp—they’ve been tested in real-world environments. Their work has been “stickered” by trusted industry leaders or open-source communities. You can’t fake that kind of credibility.

When a new project lands on my desk, I don’t start with tools or timelines. I start with people. Who’s already done something like this? Who’s solved this kind of problem before? Hiring isn’t a transaction. It’s building a team that can execute and scale—sometimes even rewrite the playbook.

How We Find and Vet the Right Talent

We don’t just look at resumes. We look at repos, contributions, and how people solve problems under pressure. A candidate who’s shipped code at a high-growth startup or led a critical open-source project? That’s a signal, not just a skill set.

And just like a coin dealer who can restore or grade a rare piece, we value engineers who can improve systems—not just maintain them. The ones who can take a slow, brittle API and rebuild it to handle 10x load? That’s the kind of talent that moves the needle.

Assembling a Team That Works—Not Just Wears Headphones

High-performing teams aren’t built by stacking resumes. They’re built by pairing depth with breadth. I look for a mix: architects who think in systems, developers who write clean code, and problem-solvers who ask “why?” before “how?”

Think of it like curating a coin collection. You need rare, high-value pieces—but you also need solid, consistent contributors that keep the whole set strong. Balance matters.

Planning a Tech Roadmap That Actually Matters

A roadmap isn’t a checklist. It’s a living plan that reflects where the business is going—and where tech can accelerate it. Every decision should tie back to real outcomes: faster time-to-market, better customer experience, or reduced risk.

Setting Goals That Stick

Years ago, we aimed to reduce system downtime to under 0.1%. It wasn’t just about uptime—it was about trust. When sales can promise uptime, it helps close deals. When customers see reliability, they stay.

That’s how we set goals now: always tied to business impact. Reduce latency? Yes—if it cuts support tickets. Modernize infrastructure? Only if it speeds up deployment or cuts costs. No vanity projects.

Staying Flexible When the Market Shifts

We planned a 24-month migration to Kubernetes. Then, a key vendor changed their pricing model overnight. We didn’t stick to the plan—we adapted. We paused full migration, focused on containerizing only the high-cost services, and saved six figures in cloud spend.

Flexibility isn’t weakness. It’s what keeps us moving forward, even when the ground shifts.

Spending Tech Budgets Wisely—No Wasted Dollars

I treat every dollar like it’s mine. Because in a way, it is. Tech budgets are limited, and every investment needs to earn its place.

Prioritizing What Moves the Business

We once spent months building a custom logging tool. It was elegant. It was ours. But it took engineers away from core product work. We switched to a proven third-party solution, saved $150K/year in dev time, and improved reliability.

Now, we ask: does this project enable revenue, reduce risk, or improve efficiency? If not, it waits—or gets cut.

Keeping Costs in Check Without Cutting Corners

Cost control isn’t about scrimping. It’s about smart choices. We audit cloud usage monthly. We automate shutdowns for dev environments. We renegotiate contracts every year. These small moves add up to hundreds of thousands in savings—money we reinvest in higher-impact work.

Leading Engineering Teams That Want to Win

My job isn’t to code—it’s to create space where engineers can do their best work. That means clear goals, room to experiment, and accountability without micromanaging.

Letting Engineers Build—and Learn

We run quarterly innovation weeks. No meetings. No deadlines. Just time to hack on ideas—new tools, process improvements, even pet projects. Last year, one engineer built a cost-forecasting script during that week. Now it’s used by our entire finance team.

Innovation doesn’t come from mandates. It comes from trust.

Holding Ourselves Accountable—With Empathy

We track progress, but we also talk about roadblocks. If a sprint slips, we don’t point fingers—we ask: what got in the way? Is the scope too big? Do they need support? Transparency builds trust. And trust builds high-performing teams.

Real Code, Real Impact

Here’s a script we actually use to keep AWS Lambda costs under control—simple, but effective:


/* Example: AWS Lambda cost optimization */

const AWS = require('aws-sdk');
const lambda = new AWS.Lambda({region: 'us-east-1'});

async function optimizeLambdaCosts() {
const functions = await lambda.listFunctions().promise();

for (const func of functions.Functions) {
const config = await lambda.getFunctionConfiguration({FunctionName: func.FunctionName}).promise();

// Adjust memory allocation for cost efficiency
if (config.MemorySize > 256) {
await lambda.updateFunctionConfiguration({
FunctionName: func.FunctionName,
MemorySize: 256
}).promise();
console.log(`Reduced memory for ${func.FunctionName} to 256MB`);
}
}
}

optimizeLambdaCosts().catch(console.error);


We ran this across our environment and cut monthly Lambda spend by 38%. No new tools. No team overhaul. Just a few lines of code that asked: “Can we do this more efficiently?”

What It All Comes Down To

Tech leadership isn’t about knowing every framework or running every server. It’s about making choices that last—hiring people who raise the bar, spending budgets where it counts, and building teams that solve real problems.

And sometimes, it’s about learning from unexpected places—like a coin collector who knows that value isn’t in the shine, but in the history, the craftsmanship, and the trust behind it.

That’s how we build technology that doesn’t just work—but matters.

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