APIs, data models, and integration decisions don’t sell in a product tour, but they determine whether software can survive at scale.
The most important decisions in software are rarely the ones users see.
After two decades in vertical SaaS, I’ve learned that the hardest problems in technology don’t show up in demos, feature comparisons, or roadmaps. They live underneath, quiet, unglamorous, and mostly invisible until something breaks.
Usability gets attention early, and rightly so. If a tool isn’t intuitive, it won’t be adopted. That’s why smaller, focused products often gain momentum quickly. They’re fast, opinionated, and excellent at solving a narrow problem.
But scale changes the rules.
As systems grow, the work shifts away from screens and toward structure. APIs. Data models. Security boundaries. Permissioning. Versioning. Backwards compatibility. Auditability.
This layer doesn’t sell well. It doesn’t fit cleanly into a product tour. And because it’s invisible when done right, it’s easy to underestimate.
Experience teaches you to be cautious of anyone who says this part is “easy.”
Enterprise-grade connectivity isn’t something you sprinkle on later. It’s not a feature you toggle on when customers ask for it. It’s an architectural posture, a set of early decisions that trade short-term velocity for long-term resilience.
That doesn’t diminish the importance of usability. It reframes it.
There’s a sequencing problem in software that many teams and buyers misjudge. Interfaces can be refined. Workflows can be simplified. Software can become more human through iteration and partnership.
Core architecture is different. Once customers depend on your data contracts, your integrations, and your system boundaries, rewrites aren’t improvements, they’re existential events.
No technology company has everything figured out. Every buyer is making a bet, whether they realize it or not.
The bet isn’t about who has the most polished experience today. It’s about which organization made the harder decisions earlier that don’t show up immediately, but compound over time.
The most enduring platforms are rarely the flashiest. They tend to look restrained, even boring, in their early years. What they’re really doing is buying optionality, earning the right to evolve without breaking the systems people rely on.
At its core, software exists to create value. That value shows up in two forms: reducing risk and enabling growth. The best systems do both, quietly and consistently.
In complex domains like preconstruction, table stakes are well understood. Cloud access, collaboration, SSO, keyboard shortcuts, drawing tools, these are expectations, not advantages. The deeper question is whether the systems behind them are designed to adapt as the world changes.
Roadmaps are promises. Architecture is proof.
As technology accelerates, the cost of architectural shortcuts increases. The decisions teams make today will determine not just what their software can do next year, but what it can survive five or ten years from now.
Those decisions rarely get applause. They do, however, leave scars.
And scars tend to be the best teachers.
Mike Roy
STACK VP of Sales
Mike Roy joined STACK in 2024 as Vice President of Sales, driving exponential growth and hitting record revenue goals within his first few months. Mike leads the entire sales organization, executing strategies to scale STACK’s footprint across general contracting, subcontracting, and supplier/manufacturers segments.
