Legacy software modernisation is one of the highest-risk decisions a board of a small or mid-sized software company will ever oversee. When it goes wrong, the damage is rarely contained. Growth stalls, churn rises, customers lose confidence, teams burn out, and the company’s strategic options narrow.
Software companies that have been around for 10–15 years or more typically face one of two challenges. The first is migrating a long-standing desktop or on-premise product to a SaaS model. The second is modernising an early-generation SaaS product that, over time, has accumulated technical debt, UX complexity, brittle integrations, and architectural constraints that make innovation slow and expensive.
As a CEO I’ve had my fair share of such challenging projects. As a board member of small-medium sized software companies, I’ve experienced first-hand what success and failure look like when it comes to product modernisation.
SaaS product modernisation is not an IT project. It is a business transformation that touches pricing, packaging, customer success, revenue predictability, data strategy, operating model, and ultimately company valuation. Treating it as a technology upgrade materially reduces the likelihood of success.
Yet, in too many boardrooms, the same pattern repeats.
The board approves a budget. The CTO is tasked with “modernising the product”. Progress is monitored through delivery milestones. The board re-engages only when warning lights are flashing: missed deadlines, cost overruns, unhappy customers, deteriorating SaaS metrics.
Boards that allow the conversation to start with:
“Engineering estimates X months and X headcount. Can we approve the budget?”
have already missed the point.
That is an execution question. The board’s job is to insist on answering the strategic ones first.
The most effective way boards can support executive teams is by ensuring that modernisation is anchored in a clear and explicit product strategy.
In a SaaS context, modernisation moments represent a rare opportunity to rethink not just how the product is built, but what kind of SaaS business the company wants to be. Markets evolve quickly. Customer expectations are shaped by category leaders. AI capabilities are resetting baselines. Pricing and packaging models change. Distribution and GTM motions mature.
While the company’s original mission may still be valid, the way value is delivered through the product almost certainly needs rethinking.
Key questions must be answered upfront:
- Who is our ideal customer profile today and in the future?
- What problem do we solve better than anyone else?
- What outcomes are customers willing to pay for on a recurring basis?
- How do we design for adoption, expansion, and retention, not just feature parity?
- How do data, integrations, and AI capabilities fit into the product’s future?
This is the role of product strategy.
Product strategy is the master plan for achieving sustainable product success in a SaaS model. It explicitly connects product decisions to customer value, commercial outcomes, and long-term scalability. Without it, modernisation often results in a technically improved product that still struggles with adoption, monetisation, or retention.
Roman Pichler’s Product Vision Board is a highly effective framework for aligning boards and executive teams on product direction. It provides clarity on vision, target users, unmet needs, differentiated value, and business goals, creating a shared foundation for decision-making.
What a SaaS-focused product strategy enables
Discussing and reviewing such a product vision board during board meetings is a very constructive way of getting a holistic view of the product modernisation project and align the board and the executive teams.
Given the overarching nature of the Product Vision Board this approach requires the collaboration of all business functions which is critical. Furthermore, it provides the teams a decision-making framework for the required aspects of all successful product modernisation project. In particular:
- Decide on the right modernisation approach. The typical approaches are refactoring, rebuilding, replatforming or encapsulation. The product strategy will help to decide on the right way forward with important consequences, as each approach will have different risk profiles, different resource requirements, timelines and impacts on existing users.
- Decide on team structure and who will lead the project. This can be a difficult one for small-medium sized companies as in many cases they don’t have an established product management team. Working on the product vision board and resulting product strategy will help clarify the required human resources, highlighting any skills gaps and will help establish the best project leadership structure. A controversial thought but I have experienced that in most cases it is better if the individual who was the leading figure in designing and developing the legacy product is not leading the product modernisation project. This can increase the opportunity to have a fresh perspective when developing the new product.
- Establish the product modernisation roadmap. Only after the product strategy is defined, the modernisation approach chosen, and the product leadership clarified does it make sense to establish a product roadmap. When it comes to product modernisation projects the related data migration plan is often an underestimated component in the roadmap.
- Creating AI and data optionality. Modern SaaS strategies must explicitly consider data foundations and AI readiness. Even if AI is not immediately monetised, architectural decisions made during modernisation will either enable or severely limit future differentiation.
For small and mid-sized software companies, product modernisation must be treated as a core SaaS business strategy, not an engineering initiative. It requires active board engagement, cross-functional alignment, and a clear view of how the product supports recurring revenue, scalability, and long-term value creation.
When product strategy is clear, execution becomes focused, trade-offs become explicit, and modernisation shifts from a risky rebuild exercise to a strategic reset.