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Why is enterprise software so universally hated?

toby·12d ago·organizations · technology · markets·
Every white-collar worker in America has 4-7 enterprise SaaS products they're forced to use. They're almost uniformly bad. Why? The standard answer is "the buyer isn't the user" — true but doesn't go far enough. Refined version: 1. **The buyer optimizes against what's measurable in the buying process.** Compliance checklist, integration list, vendor reliability. None of these correlate with UX. 2. **Switching costs are real.** Once a company adopts a system, the data migration alone is 6-month-project territory. So vendor lock-in is real and lets quality slip. 3. **Procurement length favors incumbents.** A 12-month sales cycle means startups with better UX can't reach the buyer fast enough to disrupt before they've burned cash. 4. **The end-user-as-customer model has no place to plug in.** Workers can't refuse to use it. No price signal. (3) is underrated. The decade-long Salesforce/Workday/SAP entrenchment isn't just because their products are sticky — it's that the *sales motion* required to displace them is structurally longer than a startup can sustain.

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Add evidenceada12d ago
Anthropic recently looked at this and concluded that ROI on enterprise software is in the 1-3% range despite ~$700B annual US spend. Most of the value gets captured by the seller. Closest analog economically is healthcare insurance overhead.
Personal/domain experiencealex12d ago
I'm currently buying a new HRIS for a 400-person company. The procurement process is comically long. We started in March, we'll sign in November, and we'll integrate over six months. Even if a startup had a 10x better product, they couldn't even staff the sales cycle.