Following up on my earlier piece: Build, Buy, or AI-Build, in which I noted Marty Cagan’s view that AI will not easily replace enterprise solutions, even in the age of “vibe coding.” His reasoning is sound: enterprise products are deeply embedded in intricate workflows, with business rules and integrations that can’t be swapped out overnight. Today, tools like Copilot or low-code builders tend to play a helper role rather than a wholesale replacement.

But this window may not stay open forever. While complexity and business rules protect enterprise vendors today, poor user experience erodes that advantage over time. Teams will always find creative ways to avoid clunky workflows, even when tools are mandated. The danger for product managers is assuming that mandates equal adoption.

Today, in this piece, my focus is on enterprise systems used by the employees.

Captive Audience, Hidden Costs

Enterprise software often treats UX as an afterthought. The assumption is that because IT or executives require the system, employees will use it regardless. In practice, small UX friction — extra clicks, confusing workflows, poor defaults — compounds across large organizations:

  • Lost productivity: Minutes wasted per task multiply across thousands of employees.

  • Shadow IT: Teams quietly adopt easier alternatives when friction gets unbearable.

  • Weak adoption: Data quality and feature usage lag, eroding the intended ROI.

This isn’t just about tools with a user interface. Even workflow solutions orchestrated via APIs can create friction. If APIs don’t align cleanly with the way teams work, developers build brittle workarounds, or worse, they bypass the official system altogether.

Everyday Examples

Expense management systems are a classic case. Legacy tools require multiple steps to upload receipts, so employees procrastinate or submit incomplete data. Finance teams chase reports, audits become harder, and everyone loses. Meanwhile, lighter consumer-grade apps with auto-scanning features become the quiet alternative, even in “mandated” environments.

The same pattern shows up in CRMs. If logging an activity takes too many clicks, sales reps stop doing it. The CRM may be deployed company-wide, but the data quality is unreliable, undercutting pipeline forecasting.

The Risk Ahead

Cagan is right that enterprise solutions are not trivial to disrupt. But the UX gap is a growing vulnerability. AI and automation are advancing fastest, where they can simplify repetitive workflows and connect disparate systems. That’s exactly where small UX friction accumulates.

If PMs continue to treat UX as optional, they risk leaving the door open for AI-first competitors who don’t need to replace an entire system at once. They just need to replace the pain points — and once adoption shifts, switching costs fall.

The Internal Disruption Threat

Even if external competitors struggle to break in, disruption often starts inside the same company. In large organizations, different teams experiment with progressive solutions that sit closer to real customer pain points. These aren’t full system overhauls at first — they’re lightweight workflows, AI helpers, or specialized tools that relieve specific friction.

Over time, those internal solutions build momentum. They spread across teams, win executive sponsorship, and before long, they’re positioned as the “better way.” The once-mandated solution is gradually sidelined. It’s not easy, and it doesn’t happen overnight, but it does happen — especially when users are frustrated by persistent UX pain.

Takeaway for PMs

  • Don’t mistake mandates for adoption. Measure friction in time, errors, and workarounds, not just logins.
  • Treat both UI interactions and API-driven workflows as UX challenges. Orchestration that feels natural to developers and operators is as critical as clean screens for end users.
  • Make the case for UX improvements by tying them directly to business outcomes: faster workflows, fewer tickets, higher data quality.

Conclusion

Mandates buy you an entry point with users, but not engagement. The enterprise moat of complexity is real, but it’s shrinking. PMs who treat UX as strategic, not cosmetic, can keep their solutions indispensable. Those who don’t may find that “helpers” — whether external AI products or internal workarounds — become replacements faster than they expect.