How do I turn four free pilot customers into paying ones without losing all four?

Ken Washington· B2B software for HVAC dispatch, pre-revenue, four pilot customers· Registered, SaaS & Software·1w

Nine months ago I gave four HVAC companies free access to my dispatch tool in exchange for feedback and a phone call when something broke. They have been unbelievably generous with the feedback. One of them has three dispatchers in it every single day and called me on a Sunday in July because a schedule wouldn't refresh, which I took as a compliment.

None of them pay me anything. I filed the LLC in the spring, I have an accountant asking reasonable questions, and I have a spreadsheet that says I can do this for about five more months.

Where I'm stuck is the shape of the price, not just the number. Per dispatcher punishes the one company that actually uses it. Per truck is closer to how they already think about cost, but two of them are seasonal and the truck count moves. Flat monthly is the easiest to say out loud and probably leaves money behind.

I'm also scared of the conversation itself. These four people helped me build it. Charging them feels like changing the deal.

Has anyone done the free-to-paid conversation with early pilots? Did you grandfather them at a lower rate forever, or give them a year and then move them up with everyone else?

3 replies

Priya Natarajan· Named it·1w

Per truck, and I say that as someone at the stage before yours so weigh it accordingly. The dispatcher who lives in it all day is the person who has to defend the renewal internally, and per-seat pricing quietly tells them to share a login.

On the conversation: they helped you build it, which means they have more sunk time in it than you have in them. Nine months of daily use isn't a favour they're doing you anymore, it's a tool they'd have to rip out. I'd name a founding-customer rate, put an end date on it, and say the words 'I need this to be a business' out loud. The Sunday call is your evidence, not your debt.

Cheryl Dunn· Open·1w

I do the books for a handful of software people and the free-pilot stall is the most expensive habit I see, so I'll be the boring voice here. Nine months of unbilled work is real money that never shows up anywhere you can look at it.

One practical thing: whatever you land on, put it on a simple written order form with a start date and a renewal date, even if it's one page. Half my clients invoice from memory and then can't tell me in January what they actually agreed to in June. I'm not your accountant and your situation may differ, but 'five months of runway' is a sentence that should make this conversation happen this month, not next quarter.

Ken Washington· Registered·1w

The order form is a fair hit. I have four different agreements living in four email threads and one Slack message. I couldn't tell you today what I promised the seasonal one about adding trucks in the spring, which is embarrassing for someone who sells scheduling software.

Going to do per truck with a floor, a founding rate for twelve months, and a one-page order form before I send any of it. Then I'll call the Sunday guy first, because if he says no I'd rather know before I've rehearsed it three more times.

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