In this episode of Technical Debt: Design, Risk and Beyond, Maxim Silaev speaks with Erioluwa Asiru, CTO at CircleFunds, about what technical debt really looks like inside a fast-growing fintech operating in an emerging market.

CircleFunds is digitising traditional thrift savings in Nigeria: a problem that turns out to be far more complex than “building an app.” Erioluwa shares how early architectural decisions were shaped by human behavior, cultural practices, and the reality that some processes are initially "technically impossible" to digitise without breaking trust.

The conversation explores how technical debt rarely appears in one place. Instead, it emerges as a blend of architectural shortcuts, shifting product logic, regulatory pressure, and team dynamics in an environment that changes faster than most systems can adapt. Erioluwa explains the early warning signs, such as constant firefighting, repeated fixes, and system instability, that signal debt accumulation long before failure is visible from the outside.

We also dive into leadership tradeoffs: how to balance speed with system health, how to ask engineers for compromises without losing trust, and why many long-term technical problems are rooted in product and leadership decisions rather than code. Erioluwa shares her perspective on intentional debt, architectural simplicity, documentation as a first-class artifact, and why infrastructure debt is the one category she would never knowingly accept.

The episode closes with a practical discussion on AI in fintech engineering: where it accelerates delivery, where it becomes dangerous, and why critical financial systems still demand human judgment, strong standards, and rigorous testing.

This conversation is a grounded look at technical debt as a leadership and risk problem, shaped by pressure, ambiguity, and real-world constraints.

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https://www.linkedin.com/in/dr-nikita-golovko

In this episode of Technical Debt: Design, Risk and Beyond, Maxim Silaev is joined by Rob Broadhead, a technology leader with more than 30 years of experience across enterprise systems, startups, and consulting.

Together, they explore how technical debt actually creeps into systems: not through bad engineering, but through reasonable decisions made under pressure. Rob shares early-career scars, leadership failures without happy endings, and hard-earned lessons about how debt becomes normalised inside teams.

A large part of the conversation focuses on modern tooling and AI. While AI promises speed, Rob explains how “vibe coding” and unreviewed AI output can quietly amplify existing problems: shifting debt from code into architecture, design, and assumptions. When teams stop asking the right questions, systems slow down, trust erodes, and recovery becomes expensive.

This episode also dives into leadership responsibility: why strong teams still fail, how lack of authority distorts decision-making, and why delaying cleanup for “one more release” almost always backfires.

If you are a CTO, architect, or technical leader navigating growth, AI adoption, or mounting complexity, this conversation will feel uncomfortably familiar.

Topics covered:

• Where technical debt is really born
• How bad patterns become “normal”
• AI as an accelerator of existing habits
• Early non-technical warning signs of dangerous debt
• Why cleanup efforts fail — and how to avoid that
• Leadership habits that prevent debt from becoming a way of life

Connect with Rob on his website.

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https://www.linkedin.com/in/maxim-silaev
https://www.linkedin.com/in/dr-nikita-golovko

In this episode of Technical Debt: Design, Risk and Beyond, hosts Maxim Silaev and Nikita Golovko break down one of the most widely documented technical-debt disasters in modern enterprise IT: the failed 2018 TSB Bank migration. More than two million customers lost access to their accounts, systems malfunctioned for weeks, and leadership was forced to answer to regulators.

But behind the headlines lies a deeper lesson: technical debt exists at multiple layers: strategic, product, and architectural, and TSB’s collapse showed how these debts compound when communication fails.

Maxim and Nikita unpack:

• Strategic debt: rushed timelines, misaligned goals, and a pressured migration from Lloyds to Sabadell’s platform
• Product debt: incomplete integrations, insufficient testing, and delivery pressure that forced release of known defects
• Architectural debt: brittle interfaces, undocumented dependencies, and an infrastructure designed for a different business context
• Communication debt: silos between leadership, engineering, and vendors, amplifying risk until it became unavoidable

Drawing from their own experience assessing technical debt for organizations, the hosts explain how to recognize early warning signs, measure debt at every level, and communicate risks effectively to leadership.

TSB is more than a failure story, it is a blueprint for understanding how technical debt grows, how it hides, and how it can paralyze an entire company when left unmanaged.

Next episode: How to quickly evaluate the technical debt volume in your organization.

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Reach us @ LinkedIn:

https://www.linkedin.com/in/maxim-silaev
https://www.linkedin.com/in/dr-nikita-golovko