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Dan Van Tran (DVT) is the CTO of Collectors Holdings, a leading player in the collectibles industry. Since its $850 million dollar acquisition in 2021, Tran has spearheaded efforts to integrate machine learning, robotics, and microservices to enhance collectors' experiences. In two years, Collectors Holdings' valuation skyrocketed to $4.3 billion dollars largely due to its technical and operational transformations.  

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Tran talked through one of the most difficult challenges tech and product leaders must solve: building transformational technology on top of aging technology. Here are four takeaways for building on top of existing tech debt.

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Craft a vision for the future

Bringing legacy technology into the modern era requires defining the future state of the organization. This means, not only envisioning where the company should be in the future but also clearly articulating the goals and desired outcomes. To achieve this technological vision, it is crucial to assess each existing system comprehensively, understanding their strengths, weaknesses, and dependencies. Creating relationship diagrams helps map out the connections between different systems, providing a holistic view for strategic planning.

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Prioritization is king

While sequencing and planning are essential, ruthless prioritization and assertive decision making are critical for success. Dedicating sufficient resources towards the transformation and being willing to make tough decisions, including leaving behind old systems, is important. Tran’s advice is to be aggressive in moving away from legacy code and focus on building new, more efficient systems. This might involve allocating a significant portion of engineering resources to migration efforts, even if it means diverting attention from developing new features.

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How do you get further faster? Identify the key components, even beyond the foundation, that will make the biggest difference in helping to build a new technical foundation. Then, remove all distractions and laser focus your efforts. If you do not, it only makes the process longer, less ambitious, and less effective.  

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Simplify complexity and tailor your approach

Legacy systems are inherently complex, so you should adapt your strategies accordingly. In cases where the code resembles a tangle of spaghetti and modularization is challenging, take a focused approach to future state planning. Rather than attempting to modularize everything, concentrate on key components and understand enough about inputs and outputs to replicate desired outcomes in a different way. Additionally, tailoring migration strategies to each system is crucial. This involves developing specific plans for migrating individual systems as well as establishing an observability and incident management layer early on to address issues promptly.

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Technical transformation requires cultural transformation

Cultural shifts lay the foundation for any lasting organizational transformation. To drive a successful transformation, it is essential to prepare the team mentally and align them with the change to come. Tran’s experience exemplified this challenge. At Collectors, where a small team of engineers, with an average tenure of 10 to 15 years and even upwards of 24 years, became ingrained in their established ways.

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Inspiring the team with a compelling vision, challenging their preconceived limitations, and instilling the belief that they could transcend the status quo is essential to influencing your team to achieve great feats. Cultural transformation rooted in an inspiring collective vision can become the catalyst that propels a team to embrace and execute change.

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Breaking down your tech debt and applying a customized strategy for each situation will allow you to balance innovation and tech debt resolution. While you will never escape technical debt, you must manage it. The companies that can overcome their technical debt hump, however, can achieve amazing outcomes and reach new heights.