Been in operations for 8 years across 3 companies and these “features” have caused more damage than any competitor or market downturn:

1. Auto-categorization of contractors

Sounds great until the system decides your UK contractor is actually an employee. happened at the last company I worked for, triggered a full audit… and thousands in penalties

1. ‘Smart’ payment scheduling

Gusto’s system “optimizes” payment dates for cash flow. except banks flag irregular payment patterns as risk indicators. almost lost our credit line over this

1. Bundled compliance packages

Paying $599/month per international employee for “full compliance” when most of that is just automated filings you could do for $50. we didn’t realize until switching providers cut costs by 80%

Learned these the hard way. Any “helpful” features have backfired for you?