Technical Wealth: The CTO’s Hidden Advantage in Legacy Systems

The first in a series on how engineering leaders can transform legacy liabilities into competitive advantages

The Legacy System Tax Most CTOs Are Silently Paying

Sarah, a CTO at a fast-growing fintech startup, watched as her team’s deployment frequency steadily declined:

Year 1: Weekly deployments were standard
Year 2: Monthly deployments became the norm
Year 3: Deployments happened “only when absolutely necessary”
Each deployment required three engineers for approximately six hours, with frequent rollbacks. The impact on velocity was staggering — the ability to ship new features decreased by 65% over 18 months.

Sound familiar?

As CTOs and engineering leaders, especially at growing companies, we’ve been conditioned to think about “technical debt” — that accumulation of shortcuts and deferred maintenance that eventually slows everything down.

But what about its positive counterpart?

Introducing Technical Wealth

Let’s talk about “Technical Wealth” — the competitive advantage gained from high-quality, maintainable code and efficient deployment processes that compound over time to create business value.

Technical wealth isn’t just nice-to-have engineering purity; it directly impacts business outcomes:

Companies with high technical wealth demonstrate 2–3x faster time-to-market for new features
They report higher engineer satisfaction and retention (crucial in today’s hiring market)
They show measurably better financial performance compared to technically indebted counterparts
According to DORA research, high-performing engineering teams deploy 208 times more frequently than low-performers, with lead times that are 106 times faster.

This isn’t just an engineering metric — it’s a business advantage.

The Hidden Cost Calculator

Most engineering leaders have an intuitive sense that legacy systems slow them down, but without concrete measurements, it’s difficult to prioritize and justify investments in modernization.

Here’s a simple calculation that might shock you:

Monthly Cost of Technical Debt = 
(Engineer hours spent on workarounds per month) × (Engineer hourly cost) +
(Delayed feature value per month) +
(Incident recovery costs per month)

For a team of 10 engineers spending just 10% of their time on legacy workarounds, with an average salary of $150,000, this represents over $12,500 in direct costs monthly. Add the opportunity cost of delayed features and incident recovery, and the total can easily exceed $50,000 per month — over $600,000 annually.

This “technical debt tax” compounds over time as systems become increasingly difficult to maintain. The longer modernization is delayed, the more expensive it becomes to implement.

The CTO’s Modernization Dilemma

When facing legacy system challenges, engineering leaders typically consider three traditional approaches:

• Complete Rewrites: Tempting but risky — research shows 70% exceed budgets by an average of 60%, and many never reach feature parity with the systems they replace.
• Consultants: Expensive ($200–500K for moderate projects) with limited knowledge transfer and misaligned incentives.
• Do Nothing: No immediate disruption, but technical debt compounds like credit card interest while competitors with better technical wealth eventually outpace you.
  But there’s a fourth option that most engineering leaders miss.

The Fourth Option: Incremental Acceleration

There’s a better approach that balances risk and reward: incremental acceleration.

This methodology focuses on:

• Improving deployment pipelines for legacy systems without changing the systems themselves
• Gradually refactoring critical components based on business impact
• Building technical wealth alongside existing development work
• Measuring and demonstrating progress continuously

The DORA State of DevOps reports consistently show organizations implementing these practices achieve significant improvements:

• Multiple times faster deployment frequency
• Substantial reduction in production incidents
• Improved engineer satisfaction and retention
• Better alignment between technical teams and business stakeholders
• And all without the risk of rewrites or the expense of consultants.

The Technical Wealth Score

How do you know if you’re building technical wealth or just treading water?

The Technical Wealth Score measures your engineering organization’s ability to create and sustain business value through technology. It consists of five key components:

• Deployment Velocity: How efficiently you deliver code to production
• Code Maintainability: How easily your codebase can be modified and extended
• System Stability: How reliably your systems operate
• Engineering Velocity: How efficiently your team converts effort into value
• Knowledge Distribution: How well information is shared across your organization

Each component can be measured objectively and improved systematically.

Next Steps: Assessing Your Technical Wealth

This is the first in a series of articles exploring the Technical Wealth framework and how it can transform your approach to legacy systems.

In the next article, I’ll share the detailed methodology for calculating your Technical Wealth Score and identifying your highest-leverage improvement opportunities.

For now, I encourage you to reflect on a simple question: What would your business be capable of if your legacy systems were 5x faster to deploy and maintain?

References & Further Reading

_We’re building Swift to help engineering leaders implement the Technical Wealth framework with big tech-like dev tooling at a budget price. We’re sharing our journey publicly as we build this solution. Follow along on Twitter/X or connect with me on LinkedIn.

If you’re a CTO or engineering leader struggling with legacy systems, I’d love to hear about your challenges. Reply to this article or DM me — your input will directly shape the solution we’re building._