Overcoming legacy systems: Strategies for successful upgrades

Upgrading from legacy systems to modern solutions can feel overwhelming. It demands a significant investment, effort, and a well-thought-out strategy to tackle challenges like system complexity, project fatigue, and scope creep. It’s no surprise that many equipment finance businesses stick with outdated tech and processes to avoid the hassle of digital transformation. But it doesn’t have to be that hard.

In a recent webinar, Colin Fleischmann, VP of Business Development at Odessa, and Regina Russ, Managing Director of Asset Finance at Accenture, discussed the challenges faced by equipment finance businesses trying to maintain the status quo. They also explored the steps these businesses can take to break free from a cycle of compromise and move toward long-term success.

The conversation covered key issues like technical debt, security risks, non-future-proof software, and the shortage of specialized talent for these projects. Regina wrapped up the session by addressing some of the most pressing questions from the audience.

In this blog, we’re revisiting the key insights Regina shared in her answers:

• Embrace API-First Architecture: Legacy technology limits scalability. Adopt a modular, API-first approach to meet agile business demands.
• Ensure Vendor Long-Term Viability: Ask vendors about their future product evolution and support plans to ensure long-term relevance and avoid obsolescence.
• Start Small: Pilot systems to reduce complexity, gather data, and prove ROI before scaling.
• Prioritize Customer Value: Gather substantial user feedback to ensure the new software meets the needs of users and adds value to their experience.

Ask vendors the right questions

Choosing the right vendor for modern systems is crucial to ensure your investment remains relevant in the future. Regina outlined key questions to evaluate a vendor’s readiness:

• What technology stack does the vendor currently use?
• How often are vulnerabilities patched, and what is the upgrade model?
• What are the vendor’s release cycles and long-term evolution plans?
• Are future updates part of the package, or will they incur additional costs?

“It’s important to not only assess what the vendor offers today but also how they’ve evolved in the past and how they plan to evolve in the future,” she stressed. This ensures you’re investing in a solution that won’t become obsolete in a few years.

Regina highlighting why thoroughly evaluating vendors is crucial for choosing a future-ready solution.

Start small, simplify, then scale

Overcoming implementation challenges starts with simplification. Regina highlighted the importance of piloting systems on a smaller scale before a full rollout to avoid unnecessary complexity. This approach allows you to test solutions, address problems early, and ensure the program delivers real business value.

“Start with one or two key use cases that will deliver the most impact,” Regina suggested. “Trying to do too much at once creates contract complexities, confuses your teams, and undermines success.”

By piloting systems, you can measure success using relevant metrics, gather meaningful data, and quantify ROI. Once the foundation is established, it becomes much smoother to scale the solution to additional processes or markets.

Furthermore, to prevent scope creep, you should concentrate on the true business needs rather than perceived solutions, allowing for flexibility in how features are delivered.

Regina sharing how to implement a new system incrementally by focusing solely on core business needs.

Customer feedback is the true measure of success

The success of a system implementation isn’t defined solely by defect counts or performance metrics. “Your customers’ experience is the ultimate benchmark,” Regina stressed. By engaging with end users early in the implementation process, you can ensure the solution aligns with real-world needs and expectations.

She highlighted an MVP (Minimum Viable Product) approach to gather quick, iterative feedback from customers. This ensures that the system provides practical value while enabling teams to refine features before full implementation.

“Involve your users as key stakeholders,” Regina explained. “It builds trust, enhances user adoption, and ensures the system delivers measurable results.”

A strategic approach is non-negotiable

Successful system implementations require more than just technological change—they demand a redefinition of processes and a focus on delivering customer value. Start small, prioritize user needs, and partner with trusted experts to guide your journey. With the right strategies in place, your business can overcome challenges and deliver sustainable success.

Schedule a conversation with us to discuss how you can approach this digital transformation and protect your business from the limitations of legacy software.