Software Modernization Challenges and Solutions: Expert Opinions Unveiled

It is quite some time now that we have been providing services on application modernization and we can safely say that it has been enriching from both ends. However, we have been receiving some questions that left us wondering if the modernization of software applications is a one-and-all solution for outdated legacy applications.

We reached out to industry experts, seasoned professionals, and stalwarts in the field for their invaluable insights, and indeed, we discovered the answers we were seeking.

The exact question that we asked was – “Software if not modernized starts to lose its edge, become expensive to maintain, and adding new features becomes challenging. Have you been in such a situation and how did you overcome it?”

Let us navigate through the various responses we received.


Vladimir Terekhov
CEO of Attract Group

I’ve encountered numerous situations where software applications become outdated, leading to increased maintenance costs and difficulties in feature expansion. Here’s how we’ve tackled these issues:

  1. Assess and Plan: We start by assessing the current state of the software to understand its architecture, dependencies, and the technical debt it carries. This helps us create a detailed modernization plan that aligns with business goals.
  2. Incremental Modernization: Rather than a complete overhaul, we often recommend an incremental approach. This allows us to modernize parts of the system systematically, minimizing disruption and spreading costs over time.
  3. Embrace Agile and DevOps: Implementing Agile methodologies and DevOps practices helps streamline the modernization process. This ensures continuous integration and delivery, allowing for faster feature updates and more efficient maintenance.
  4. Refactor and Re-architect: We refactor code to improve its structure without altering external behavior, and re-architect systems to be more modular and scalable, making future updates less cumbersome.
  5. Update Tech Stack: Updating the technology stack is crucial. We introduce modern frameworks, programming languages, and tools that are better supported and allow for easier feature integration.
  6. Focus on User Experience: Modernization isn’t just about the backend. We also revamp the user interface and experience to meet current standards and expectations, which helps in retaining and growing the user base.


Billy Parker
Director at Gift Delivery

In my role as Director at Gift Delivery, I have overseen the modernization of our software to keep up with the ever-changing e-commerce landscape. This process involved updating our systems and implementing new technologies to improve efficiency and enhance user experience. I have also worked closely with our IT service company representatives to ensure a smooth transition and minimize any potential challenges.

From my experience, I have learned that modernizing software is crucial for businesses to stay competitive and meet the evolving needs of customers. Not only does it improve the overall performance and functionality of the software, but it also reduces maintenance costs in the long run. However, I understand that this process can be daunting and challenging for many companies, especially when it comes to adding new features. That is why it is essential to have a strategic plan in place and work closely with experienced professionals.


Mervyn O’Callaghan
Co-Founder and CEO of CameraMatics

It is essential to modernize software to stay competitive in the vehicle safety tech space. Software that needs to be updated can quickly become a liability with ballooning maintenance costs. It also makes it challenging to roll out new features that meet customers’ needs today.

We’ve had moments where our software started showing its age. Recognizing the risks of falling behind, we took a proactive approach to improve and innovate continuously. This wasn’t just patchwork fixes – we fundamentally reevaluated our entire software architecture to make sure it could scale, integrate the latest technology, and be flexible for the future.

A key strategy was adopting a modular design. This allowed us to update pieces of software without disrupting everything, reducing maintenance costs and making it smoother to launch new capabilities. Embracing cloud tech gave us more scalability and performance to meet demands efficiently.

We also nurtured a DevOps culture, improving collaboration between development and operations teams. This sped up development cycles, boosted software quality, and made us more responsive to user feedback. Moreover, we prioritize customer-driven innovation by regularly talking to users. This keeps our modernization focused on solving real-world problems they have and adding value to their operations.

Staying ahead of software aging took a blend of new architectural principles, teamwork, and nonstop customer focus. This approach has kept our software current and at the leading edge in providing cutting-edge fleet safety solutions.


Connor Ondriska
Co-Founder and E-learning Expert from SpanishVIP

We have encountered the challenges that come with outdated software. When our software started to lose its edge, it became expensive to maintain, and adding new features became increasingly challenging. However, we were determined to overcome this situation and ensure our technology remained up to date.

To tackle the issue, we adopted a two-pronged approach. First, we conducted an in-depth analysis of our existing software, identifying its limitations and areas that needed improvement. This assessment helped us understand the specific pain points and allowed us to prioritize the most critical aspects of modernization.

Once we had a clear understanding of the areas requiring attention, we embarked on a comprehensive software modernization process. Our team collaborated closely with experienced software developers and industry experts to revamp our technology stack. We focused on adopting modern programming languages, frameworks, and architectures that would enhance the performance, scalability, and maintainability of our software.

During this process, we faced several challenges, including the migration of existing data and the integration of new features seamlessly. To address these challenges, we followed a systematic and phased approach. We started with a thorough testing and quality assurance process to ensure the stability and reliability of the updated software. We also implemented robust data migration strategies and performed rigorous testing to minimize any disruptions to our operations.

To ensure the successful adoption of the modernized software, we placed a strong emphasis on user training and support. We provided comprehensive training sessions to our instructors and staff, ensuring they were well-equipped to utilize the new features and functionalities effectively.

We also established a dedicated support team to address any issues or concerns that arose during the transition period, ensuring a smooth user experience for our students.


Aziz Bekishov
DC Mobile Notary, Founder of UNmiss

As the founder of, I’ve navigated the complex journey of software modernization firsthand, ensuring our tech remains competitive and efficient.

Embracing Agile and Continuous Integration: Software modernization is imperative for staying ahead. At, we faced increased maintenance costs and difficulties in implementing new features due to outdated technology.

We overcame these challenges by adopting an agile development approach, focusing on continuous integration and deployment. This allowed us to iteratively update our software, integrating modern technologies and methodologies gradually, rather than attempting a complete overhaul at once. This incremental update strategy reduced risk, improved efficiency, and ensured our software could easily adapt to new requirements.


Lilia Stoyanov
CEO of Transformify

One key hurdle we encountered was the disconnect between HR software selections and existing IT infrastructure. Witnessing the frustrations caused by incompatible tech stacks, we now emphasize seamless integration as a core value. This means offering solutions that easily connect with existing systems, minimizing costly customizations, and ensuring a smooth implementation process.

Beyond the technical, I firmly believe in the power of community and the exchange of ideas with fellow entrepreneurs. By constantly learning and sharing experiences, we fuel innovation and overcome challenges together. And when it comes to funding our growth, we prioritize maintaining control and building a sustainable, profitable model. This has led us to explore diverse options beyond traditional VC funding, allowing us to expand globally while staying true to our vision.


Molly Haines
Owner of Cash Home Buyers

Let me share my point of view based on my personal experience.

Assessment and Planning:

  • Start by thoroughly assessing the software, examining its technology stack, architecture, codebase, and potential risks.
  • Formulate a detailed plan based on the assessment findings to guide the modernization process effectively.

Choosing the Right Approach:

  • Consider various modernization approaches such as re-platforming, re-architecting, refactoring, or rebuilding from scratch.
  • Choose the approach that best suits the project’s specific needs, constraints, budget, timeline, resource availability, and desired outcome.

Incremental Modernization:

  • Instead of overhauling the software all at once, adopt an incremental approach.
  • Break down the modernization process into smaller, manageable tasks and tackle them one at a time.

This approach minimizes disruption to ongoing operations and allows for continuous improvement.


Brenton Thomas
Founder and CEO of Twibi

The modernization of software applications is crucial for staying competitive in the digital landscape. Evidence suggests that updating legacy systems enhance efficiency and agility, driving business growth. For example, migrating to cloud-based platforms improves scalability and accessibility, facilitating seamless user experiences.

This underscores the importance of embracing modern technologies to meet evolving consumer demands. As a SaaS SEO agency, assisting clients in software modernization efforts aligns with our expertise. By optimizing applications for search visibility and user engagement, businesses can maximize their online presence and attract a broader audience. Thus, prioritizing software modernization ensures long-term success in today’s dynamic marketplace.


Abhishek Deshpande
Founder of Peenak Solutions

In the ever-evolving landscape of technology, the imperative to modernize software applications is not just a choice but a necessity for sustainability and growth. As the founder of Peenak Solutions, I’ve navigated the complex journey of software modernization, balancing the cutting-edge with the time-tested.

Software modernization is akin to renovating a historic building; it’s about preserving the essence while upgrading the infrastructure for the future. In my experience, maintaining relevancy and efficiency in software applications is an ongoing process of adaptation and foresight. We’ve tackled the challenge of modernization by focusing on three pivotal strategies:

Embracing Cloud Technologies:

Transitioning to cloud-based services has been a game-changer, offering scalability, flexibility, and a significant reduction in maintenance costs. This move streamlined our operations and enabled us to integrate advanced features seamlessly.

Investing in Continuous Learning:

The tech field’s constant evolution demands perpetual learning. At Peenak Solutions, we prioritize upskilling and reskilling, equipping our team with the latest programming languages, frameworks and best practices. This approach has empowered us to tackle modernization challenges head-on, with a toolkit ever-ready for innovation.

Fostering Community Engagement:

Leveraging the collective wisdom of the WordPress community and beyond has provided invaluable insights into modernization pitfalls and successes. Through active participation in meetups, WordCamps and online forums, we’ve exchanged strategies with peers, staying abreast of trends and technological advancements.

A notable instance of our modernization effort was overhauling a client’s aging content management system. The project involved:

  • Migrating to a more flexible, scalable WordPress solution.
  • Integrating modern SEO practices.
  • Enhancing user experience with responsive design.
  • This transformation resulted in a 50% increase in user engagement and a significant reduction in maintenance costs, exemplifying the tangible benefits of modernizing with purpose and precision.

In essence, the modernization journey is about upgrading software and fostering an ecosystem of continuous improvement, innovation, and community collaboration. It is a testament to the fact that while technology may evolve, strategic foresight, adaptability, and community engagement remain constant.


Praveen C

CTO at eTakeaway Max UK

The pace of technological advancement makes keeping software up-to-date an essential yet tricky balancing act for companies nowadays. Transitioning to a modernized ePOS for takeaway and food delivery systems can accelerate an organization’s broader software modernization efforts. As both a CTO and occasional consultant, the strain legacy systems can put on organizations firsthand when core applications start showing their age.

Sure, at first it seems easier to keep the status quo running. But soon the cost and headaches of maintenance pile up, performance lags, and any new features require unpleasant hacks. Before you know it, your company feels stuck, frustrated, and hemorrhaging money into ancient tech – not great for morale or the bottom line!

The key is being proactive and setting aside dedicated resources for modernization projects before dire situations appear. We advise CEOs to collaborate closely with their CTOs and product leads early, map out priority areas in need of updates, invest in skills training for personnel, and migrate to more agile frameworks.

This way pieces can modernize gradually without a huge disruption overnight. Does this mean extra upfront work? Absolutely. However staying on top of regular improvements, cloud migrations, and modular architecture pays for itself quickly via enhanced security, efficiency, and developer velocity. Plus, it prevents the business risks of sudden legacy failures.

Trust me, we’ve been on both sides! Whether an outdated legacy app or acquiring outdated companies, incremental modernization comes with short-term growing pains but keeps technology and processes moving in the right direction. And it beats waiting until an old system finally dies, taking your operations down with it. Set aside the time now to future-proof. Your customers and employees will thank you!


Matt Aird
CTO at Custom Neon

Software modernization is a challenge we’ve faced at Custom Neon. We need to update and maintain our software to guarantee scalability and cost-effectiveness while preserving our competitiveness. When software starts showing its age, it indeed becomes a resource sink, both in terms of maintenance efforts and the added complexity of introducing new features.

One key instance where we encountered this issue was with our internal order management system. As we grew, the system, which was initially strong, began to lag in performance and flexibility. The development team had to commit substantial resources to every new feature request, and maintenance costs went up.

Our strategy for conquering this obstacle was diverse. To determine which parts of the current system were necessary and which we could live without, we first thoroughly audited it. This made figuring out which essential components needed maintenance and enhancement easier.

After that, we made the decision to use a microservices design, which divided the system into more manageable, smaller parts. By allowing numerous teams to work on several services at once, extending the system’s lifespan, and simplifying updates, this enhanced development.

Additionally, we leveraged cloud technologies since they gave us the scale and flexibility we needed to grow. Our system’s overall reliability increased and our hardware maintenance costs decreased when we made the switch to the cloud.

To further automate our deployment and testing processes, we also invested in continuous integration and deployment (CI/CD) pipelines. This made it possible for us to promptly roll back modifications in the event that problems developed, and it also greatly decreased the time and work needed to introduce new features.

It was also essential for creating a culture of lifelong learning among our IT staff. To keep our developers aware of emerging technologies and industry best practices, we provide them with training and information. They may now tackle difficulties creatively and innovatively as a result.


Vasyl Magometa
CTO at Reenbit

Software modernization is important, but unfortunately, it’s often neglected. This leads to a scenario where product owners initially receive outdated working software, resulting in technical limitations and slower development.

Finding a balance between time spent on feature development and product gardening is significant. It’s all about the active cooperation of technical leadership (architects, tech/team leads) and product owners who naturally care about the business and need assistance from a technical perspective.

Judging from personal experience, the sooner you start modernization, the higher your chance is to stay tech-trendy and competitive. Ideally, conversations about upgrading dependencies, replacing not-supported ones, and rewriting critical parts with new technology (a better one) must happen regularly and turned into actions.


Sergiy Solonenko
Founder and CMO of Algocentric Digital Consultancy

As an expert, I would like to add some insights on this topic.

Embracing a DevOps Culture:

One of the pivotal steps in application modernization is the transition from traditional development and operations silos to a more integrated DevOps approach. This shift not only fosters better collaboration between teams but also significantly enhances the deployment and scalability of applications. It’s about creating a culture where continuous integration and continuous delivery (CI/CD) pipelines become the backbone of your development process, enabling faster rollouts and more reliable applications.

Integrating AI and ML:

Modernization also means reimagining applications to be more dynamic and intelligent. By embedding AI and ML capabilities, applications can transition from static tools to assets that continuously learn and adapt to new data. This transformation not only elevates the user experience but also unlocks new efficiencies and capabilities, making your applications more responsive to the needs of your business and your customers.

Navigating Legacy System Challenges:

Legacy systems, with their deep-rooted architectures and outdated technologies, present significant hurdles to modernization efforts. The key challenge lies in balancing the preservation of valuable legacy functions with the adoption of modern architectures and cloud technologies. This often involves strategic decisions about what to retain, what to retire, and what to completely reimagine, all while ensuring business continuity and minimizing disruption.

Leveraging Cloud Computing:

Cloud computing has emerged as a cornerstone of application modernization, offering unmatched scalability, flexibility, and cost-efficiency. Transitioning to cloud-native applications allows organizations to fully leverage the cloud’s potential, from infrastructure and platform services to software as a service (SaaS) solutions. This shift not only reduces operational costs but also accelerates the deployment of new features and services, thereby enhancing your competitive edge.

Bridging the Skills Gap:

A significant aspect of modernization is addressing the skills gap within teams, particularly in programming and cloud technologies. Investing in training and fostering a culture of continuous learning is critical to equipping your teams with the necessary skills. Encouraging experimentation and staying abreast of technological advancements can empower your organization to navigate the complexities of modernization with confidence.


Final Thoughts

The responses were overwhelming, no doubt! What we learned from these is that there are certain myths around application modernization. One among them is that modernizing is expensive, which is clearly busted from the responses we received. The other is that only revamping the UI interface is modernization.

The process that goes, in a nutshell, can be streamlined as – Assessing and Planning, Incremental Modernization, Embracing Agile and DevOps, Refactoring and Re-architecting, Updating Tech Stack, and Focusing on User Experience.

The other benefits that come with app modernization include enhanced overall productivity, additional revenue streams, and a competitive edge.

Don’t let outdated software hold your organization back from achieving its full potential. Our experts at Dignitas Digital can help you assess your current systems, identify areas for improvement, and develop a customized modernization plan that aligns with your specific needs and budget.

Get in touch for a free consultation.

Dignitas Digital