Case Study

Strategic Alignment Saves Critical Refactor at Realpad

As Fractional CTO for Realpad, I conducted a comprehensive strategic audit that uncovered critical misalignments threatening a 90k EUR refactoring project. Through skip-level interviews and rigorous analysis, we avoided a potential disaster and established the foundation for sustainable engineering leadership.

Vojtech Gintner
June 1, 2025
14 min read
Fractional CTOTechnical DebtStrategic AlignmentEngineering LeadershipOrganizational Change
Strategic Alignment Saves Critical Refactor at Realpad

Every successful software company eventually faces the same demon: Technical Debt. Realpad, a leading provider of software for real estate developers, was at a crossroads. Their core legacy Java codebase had served them well, but it was becoming a bottleneck. Innovation was slowing down, and the engineering team was pushing hard for a massive "Tech Debt Removal" project—specifically a migration to a modular architecture using modern Spring Boot standards. The challenge wasn't technical; the engineers knew how to code. The challenge was strategic alignment.

The Challenge: The "Black Box" of Refactoring

The leadership team was facing a common dilemma that threatens many growing software companies:

The Black Box: The refactoring project threatened to become a resource sink where budget (estimated at 90k EUR initially) and time would be poured in with vague promises of "future speed."

Conflicting Priorities: While engineers wanted to refactor, the business frantically needed a critical new feature set to stay competitive.

The "Bus Factor": The knowledge was siloed among a few key individuals, creating a fragile ecosystem.

They brought me in to audit the strategy, challenge the assumptions, and ensure this engineering overhaul didn't capsize the business roadmap.

The Diagnosis: Uncovering the "Kraken"

My approach as a Fractional CTO is never to just look at the code—it is to look at the decisions behind the code. To get the full picture, I conducted individual, private interviews with every key stakeholder, ranging from the C-Suite leadership down to the individual engineers on the ground.

This "skip-level" discovery process allowed me to bypass the filtered reports usually reaching the top and hear the raw, unfiltered reality from the trenches. Through this, we uncovered uncomfortable truths that were previously ignored.

Discovery 1: The Motivation Disconnect

I challenged the "Why." Was this refactor driven by business needs or engineering curiosity?

The Insight: The push was bottom-up. Engineers were frustrated with legacy code.

The Risk: During our sessions, we discovered a critical misalignment. The Lead Engineer—who was supposed to lead the business's #1 priority feature—didn't actually believe that feature was important. They were mentally checked out, focusing instead on the refactor.

The Result: The CEO realized that their top revenue-generating initiative was in the hands of someone who didn't view it as a priority.

Discovery 2: The "Agency Mode" Legacy

Realpad was suffering from what I call "Agency Mode" thinking. The engineering culture had historically been "give me specs, I'll give you features."

The Insight: Engineers were not asking why they were building things; they were just building. This meant they couldn't justify the ROI of the refactor in business terms (e.g., "This refactor will save us X hours per sprint," vs. "It cleans up the code").

The Fix: I pushed for a culture shift where engineers must understand the P&L implications of their architectural choices.

Discovery 3: The Budget Illusion

The project had a theoretical budget, but no "kill switch."

The Insight: Budget approvals were described as "pretend." There was no mechanism to stop the project if it burned 50% of the cash with only 10% of the results.

The Strategy: I introduced the "Ship Building" Framework. Treat internal teams like external contractors. Release budget in small increments (e.g., 6-week cycles). If the "ship" doesn't sail or the milestone isn't hit, funding pauses for a post-mortem.

The Intervention: Strategic "Shock Therapy"

I didn't write a single line of Java code. Instead, I re-architected their decision-making process.

1. Enforcing Radical Prioritization: I advised the CEO to institute a public "Company Priority List." We moved away from vague goals to a strict hierarchy. If an engineer is working on Task B, they must be able to explain why Task A (the revenue driver) is blocked. This exposed the fact that the team was "playing soccer while the other half was playing football." We aligned the sport.

2. Mitigating the "Bus Factor": The audit revealed that a certain sub-group of engineers were effectively irreplaceable. I advised against a siloed "Refactoring Squad" that works in a dark room for 6 months. We shifted toward Early Adoption & Rotation—as soon as a module is refactored, other teams must use it immediately. This forces knowledge transfer and prevents the "Ivory Tower" architecture that looks good on paper but fails in production.

3. The "Side Quest" Anti-Burnout Strategy: Long refactors destroy morale. Engineers turn into robots moving legacy code from File A to File B. I suggested implementing "Side Quests"—short, creative tasks unrelated to the refactor to keep the engineering mind sharp and prevent tunnel vision.

The Outcome: From Confusion to Leadership

The most valuable result of a consultation isn't always "fixing" the project—sometimes it's realizing the project needs a different captain.

Through our rigorous Q&A process, the Realpad leadership realized they lacked the internal seniority to manage a transformation of this magnitude. They were trying to navigate a storm with a crew of fishermen, when they needed a naval captain.

The tangible results:

Hiring Decision: The realization of the "gap" led them to immediately hire a senior Head of Engineering to take ownership of the execution.

Saved Resources: They avoided launching a 90k EUR project with a misaligned team, which would have likely ballooned in cost and delayed critical business features.

Strategic Clarity: The CEO and Product Leads gained a "dashboard" for decision-making—knowing exactly what questions to ask their engineering teams to validate ROI.

"I wanted to thank you for your help during this transitional period; it helped me very much. We have now onboarded an experienced Head of Engineering to take this forward." — Marián Škvarek, CEO, Realpad

Why This Matters for Your Business

As a Fractional CTO, I don't just "manage devs." I bridge the gap between business strategy and engineering execution.

Whether you are a startup facing growing pains or an established company drowning in tech debt, you need someone to ask the expensive questions before you spend the expensive money.

Are you about to undertake a major technical overhaul? The questions I ask can save you from costly misalignments before they derail your roadmap.

Conclusion

The Realpad engagement demonstrates a critical truth: the most valuable technical leadership often happens before a single line of code is written. By conducting rigorous skip-level discovery, challenging assumptions, and exposing organizational misalignments, we saved the company from what could have been a costly and demoralizing failure. The real success wasn't in executing the refactor—it was in helping leadership understand what kind of leadership they needed to execute it successfully. Sometimes the best intervention is helping a company recognize when they need to level up their internal capabilities before tackling transformational projects.

Key Takeaways

  • Technical debt projects fail more often from organizational misalignment than technical challenges
  • Skip-level interviews reveal uncomfortable truths that filtered reports miss
  • Engineers disconnected from business priorities create execution risk
  • "Agency Mode" thinking prevents teams from justifying technical investments in business terms
  • Projects need "kill switches"—clear metrics to pause and reassess if milestones aren't met
  • Radical prioritization exposes when teams are working at cross-purposes
  • Knowledge silos create fragile systems—force rotation and early adoption
  • Long refactors require "Side Quests" to prevent burnout and tunnel vision
  • Sometimes the best outcome is recognizing you need more senior leadership
  • Strategic clarity about resource allocation prevents budget waste
Vojtech Gintner

About the Author

Vojtech Gintner - CTO @ Finviz

"Turning Engineering Chaos into Business Value"

Real-world leadership, not just theory. As the active CTO of Finviz, I don't just advise on strategy—I execute it daily. I navigate the same market shifts, technical bottlenecks, and leadership challenges that you do.

With 20 years of hands-on engineering experience (from React/Node to distributed infrastructure), I specialize in turning chaotic software organizations into scalable, high-performing assets. I bridge the gap between business goals and technical reality—speaking the language of your board and your developers.

Interested in similar results for your organization?

Let's discuss how I can help your engineering team overcome challenges and achieve ambitious goals.

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