worst field sales software i've wasted money on and what to avoid

I've probably demoed or bought more CRM and field software than anyone should have to. Some of it was genuinely useful. A lot of it was expensive noise.

The worst offenders aren't always the priciest ones either. They're the ones that solve a problem you don't actually have while ignoring the real work - which is getting reps in front of customers and closing deals.

GPS tracking software that's so granular it becomes surveillance. Your reps know they're being watched at the minute level, and suddenly they're defensive about windshield time. But windshield time is where deals get thought through, you know? It's not wasted. Yet these tools treat it like theft. We dumped one that cost us $8k a year because it created more friction than it solved. Reps were gaming the system, management was obsessed with metrics that didn't move the needle at all...

Then there's the mobile CRM that requires WiFi or a strong signal. A rep's in a rural territory, needs to pull up a contact or log a call, and the app just hangs. So they don't log it. Pipeline visibility gets worse, not better. You're literally paying for data quality to deteriorate. I mean, what's the point.

Lead assignment automation that doesn't account for territory. It'll dump 50 leads on someone already crushing quota while another rep's territory sits dry. Looks efficient on a spreadsheet. Doesn't work when you're actually running routes and managing windshield time across a region.

The implementation time killed us on one platform. Two months. Promised plug and play, actually took two months. My reps lost momentum, some of them never really recovered their productivity that quarter, honestly. The software wasn't broken exactly, but the ramp time cost us real money and it wasn't worth what we got out of it.

Most of these vendors don't understand that a rep's focus needs to stay on the customer and the sale. The software should capture what happened, not require them to think about the software. But nobody's really selling that because it's boring and doesn't justify a six-figure contract, so. Yeah.