After more than three decades advising and leading technology and product teams across sectors from Telecoms to Healthcare, I’ve seen a familiar story unfold time and again—particularly in smaller services-based businesses. It starts with a team building their own bespoke system, perhaps as a natural extension of their service model or out of necessity. What begins as a pragmatic, lightweight platform—often stitched together from open-source tools—grows over time into a critical business asset.
And then, eventually, it becomes a liability.
At this point, these organisations face a fundamental crossroads: continue investing in their proprietary system, or transition to an established commercial or SaaS platform. This is often more than a technical or operational decision, it frequently coincides with a strategic funding event (whether a growth investment, M&A process, or internal restructuring). The path taken can dramatically affect future scalability, valuation, and operational resilience.
Let’s explore how companies get here and why Product Management is so critical in navigating what I call the platform dilemma.
The early build phase: Necessity breeds innovation
Smaller services businesses, especially those in niche or process-heavy sectors like insurance services, compliance, or specialised B2B operations, often find commercial platforms too inflexible or expensive in the early years. So, they start small:
- A bespoke CRM or scheduling tool to match a unique workflow.
- Custom reporting dashboards built atop open-source databases.
- Light automation platforms to streamline internal tasks.
These systems work beautifully for a while. In fact, they often give the business a competitive edge in the early years, allowing them to operate lean and deliver high-value service at pace.
But as the company scales, these tools are asked to do more than they were ever designed for: support a growing client base, integrate with external partners, comply with security regulations, or enable new business models. And that’s where the cracks begin to show.
The crossroads: Build further or buy in?
This decision point is one of the most strategically significant junctures a services business will face.
- Continue building? This path maintains control but demands increasingly significant investment in engineering, compliance, and maintenance.
- Buy or migrate? This offloads technical risk, but can force compromises in workflows, IP differentiation, or customer experience.
It’s also often the moment when new capital is on the table. Investors or acquirers will probe deeply: Is the tech stack an asset or a liability? Can it scale? Is it compliant? Does it increase or reduce risk?
This is where Product Management should be at the centre of the conversation; too often, it isn’t.
Why Product Management matters here more than ever
A strong Product team brings three critical lenses that are essential at this stage:
- Strategic clarity
Product Managers help define what’s core to the business. What capabilities truly differentiate you? What is commodity? Without this clarity, companies risk rebuilding the wrong things or prematurely abandoning capabilities that matter. - User-centric transition planning
Whether you rebuild or migrate, your users (internal or external) will experience disruption. Product teams are uniquely skilled at managing change in a user-centred way, mapping journeys, designing for minimal friction, and sequencing rollouts intelligently. - Roadmap governance and trade-offs
This stage is full of trade-offs: speed vs. robustness, feature-rich vs. sustainable, open vs. proprietary. Product Managers are trained to manage these tensions transparently and in alignment with business outcomes.
Risks of going without a Product function
Many founder-led or ops-centric services businesses grow without a dedicated Product team. But at this pivotal juncture, flying blind can lead to serious consequences:
- Technical dead-ends: Engineering teams, without product guidance, may continue building in ways that don’t align with future scale or customer needs.
- Underestimated migration pain: Businesses may assume switching platforms is simple – until they realise how embedded their bespoke workflows really are.
- Fragmented customer experience: Without product ownership, customers feel the inconsistencies as systems change, support falters, or interfaces shift.
- Misalignment with investors: Lack of clear product strategy can raise red flags during due diligence, affecting valuation or delaying funding rounds.
What to do now
If your business is approaching this crossroads, or you sense it’s not far off, here’s where to start:
- Assess the system’s true role. Is it a core differentiator or an operational tool?
- Bring in Product expertise early. Even a fractional Product Leader or consultant can help shape the early roadmap and avoid major pitfalls.
- Balance ambition with realism. A phased approach of keeping the bits that work and transitioning the bits that don’t, can often outperform a big-bang rebuild or rip-and-replace.
- Align the roadmap to funding milestones. Whether pitching to VCs or preparing for acquisition, a clear product strategy inspires confidence.
This decision point is not just about technology but is about what kind of company you want to become. Product Management helps translate that vision into tangible systems, customer outcomes, and long-term value.
Don’t wait until your system breaks to realise you need a Product team. By then, it may already be costing you more than you think.
If you’d like to discuss your business’s current tech stack or transition options, feel free to connect: we’ve helped clients in exactly this spot navigate the path forward with clarity and confidence.