The tools that made sense then
Software buying decisions at mid-market organisations are rarely revisited with the same rigour as the original selection. A Salesforce instance implemented five years ago with a different team, a different use case, and a different org structure now costs $350 per user per month for a team that uses 15% of the functionality. The renewal comes up. Someone complains. Nothing changes.
There are two reasons organisations stay on tools they have outgrown: the switching cost is real, and nobody has produced an honest analysis of what it actually is versus what staying costs.
Licence cost misaligned to usage
Enterprise tier pricing with mid-market usage patterns. Features that are licensed and never used. Add-on modules that were activated and forgotten.
Tool rigidity masquerading as complexity
Teams have built workarounds for the things the tool cannot do. The workarounds have become standard operating procedure. The tool is effectively a constraint on how work gets done.
Proliferation without rationalisation
Point solutions have been added to fill gaps in the primary platform. The organisation now pays for three tools that partially overlap, none of which does the job completely.
AI features locked behind higher tiers
The AI capabilities being sold by the incumbent require an upgrade to a tier that costs materially more — for functionality that is available in alternatives at current or lower cost.
Switching cost mythology
The belief that migration is prohibitively complex, expensive, or risky — in many cases installed by the vendor during renewal negotiations rather than established through independent analysis.
AI readiness stalled
Automation and AI initiatives are blocked because the current tooling cannot support the integration architecture they require. The roadmap is ready. The stack is not.