u/Upstairs_Employe

I build software for field service contractors.

I spend a lot of time reading why businesses switch software. The ServiceTitan pattern keeps coming up and I can't stop thinking about it.

Real BBB complaints, real numbers:

• $67,230 charged to an HVAC company, full remaining balance of a 24-month contract, even though implementation was allegedly incomplete
• $39,375 charged to a small business that cancelled 10 days into a 2-year contract
• $19,596 sent to collections

This isn't a niche problem. ServiceTitan is the dominant software in the trades industry, HVAC, plumbing, electrical. Most contractors don't have lawyers reviewing contracts before signing.

For context: the company did $772M in revenue last year and posted a $239 million net loss (SEC filing, FY2025). A public company under that pressure needs retention, and the contract structure reflects that.

My question for this community: how do you evaluate exit risk before signing a multi-year software contract? Is there a checklist you use?

Asking genuinely because I'm trying to understand what questions buyers are actually asking before they sign, because most of our customers tell us they didn't ask any of this until it was too late.

Lately I’ve been thinking about how much ChatGPT changed user expectations around software.

You type what you want.
It understands context.
It reasons.
It takes action.

But then you open most CRM/FSM/operations software and it’s still:

• dashboards
• filters
• forms
• tabs
• manual workflows
• endless clicking

So I’m curious:

Has anyone here found software that actually feels conversational and agent-driven instead of just “AI-powered” as a feature?

Something where you can genuinely say:

• “reschedule tomorrow’s jobs”
• “follow up with overdue estimates”
• “assign the nearest available tech”
• “handle after-hours calls”

…and the system actually understands and executes it.

Feels like business software UX hasn’t caught up to where AI is heading yet.