One of my four free pilots finally signed a paid contract

Ken Washington· B2B software for HVAC dispatch, pre-revenue, four pilot customers· Registered, SaaS & Software·4w

Eleven months of free pilots, and on Tuesday one of them signed for $400 a month.

For anyone who hasn't done B2B software for a trade: I build dispatch software for HVAC companies. The pilots were free because I needed to watch real dispatchers use it, and because I was scared to ask. Somewhere around month seven, free pilot quietly turned into free software, and I had four companies depending on me, a support burden, and zero dollars.

What broke it wasn't a better demo. I stopped asking whether they'd consider paying and sent an email saying the pilot ends on the 30th, here's the price, here's the link, and I'd love to keep going. Two said yes eventually, one said not this year, and one, the one I'd bent over backwards for, never replied at all.

$400 a month is not a business. It's my hosting bill plus a little. But something changed in how I talk about it. I have a customer now instead of four people doing me a favor, and I've noticed I'm much less willing to build whatever anyone asks for on a Friday night.

To everyone still in free-pilot land: set the end date. The conversation is far shorter than the year you'll spend avoiding it.

3 replies

Priya Natarajan· Named it·4w

This is the post I needed. I'm building scheduling software for independent physical therapists and I have three people using it free who all say they love it, and I have been treating 'they love it' as progress.

The line about it becoming free software is uncomfortably accurate. I did a data migration for one of them last Sunday night. Did you give the two who converted anything to soften the deadline, a pilot discount or a ramp, or did you just send the price? I keep wanting to build an elaborate off-ramp instead of writing four sentences.

Ken Washington· Registered·4w

Just the price. I drafted the elaborate version, grandfathered rate, three-month ramp, an entire tier I invented for them, and my wife read it and asked which of those things I actually wanted to be selling in five years.

I did give them sixty days instead of thirty, and I said thank you for the year properly, in a paragraph, at the top. That was the whole off-ramp. The one who never replied wouldn't have replied to a better email either.

Cheryl Dunn· Open·4w

Congratulations, and now something boring from the bookkeeper corner: sort out how you're invoicing and where that $400 lands before it becomes twelve customers.

Recurring B2B revenue is the easiest kind to lose track of, because it works by itself until it doesn't. Make sure the subscription charges land in the business account and not on a personal card you meant to switch over. I have a client who found eight months of customer payments sitting in a personal account, and untangling it for their first tax year cost them more than they'd paid me all year.

Also, in my state the moment you have recurring software revenue is worth a five-minute conversation about whether any of it is taxable. Yours will differ.

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