Before I tell you about the apps, I should tell you how far I was willing to go before they existed.
In the early 90s I was working the sugar mills in South Florida. Cell towers weren’t everywhere yet, and down among the steel you couldn’t hold a signal at all. So when a proposal had to go out, I’d climb to the top of a tall roof structure — the one spot with enough signal — and send it from my Palm Pilot, using my flip phone as the fax modem.
Standing on a roof, holding a phone to the sky so a piece of paper could appear in somebody’s office. That was state of the art. That was me trying.
The long war on paperwork
It didn’t stop there. Over the next thirty years I threw everything I had at one stubborn problem: getting a record of the work from the field to the office while it was still true.
I gave every one of my foremen a fax machine so the day’s documents could come in every night. I taught myself Windows programming and wrote my own software to track projects and time. I learned how to build servers — then remote servers, then VPNs, back when I had to explain to people what a VPN was — so my leads could dial in and enter their hours. When that was too much, I taught myself web development and built login pages, in the days of phone modems, before anything was just connected.
Every one of those systems worked, technically. And every one of them died the same death: the tool demanded more from the person holding it than the job left room for.
That’s the part nobody building “construction software” from an office ever seems to learn. A construction crew is not a room full of clerks. I’ve had brilliant field hands — guys who could look at a bundle of steel and see the building — with every level of administrative ability you can imagine. Some of the best men I’ve ever employed can barely read or write. Hand that man a system with menus and passwords and required fields, and you haven’t given him a tool. You’ve given him a reason to procrastinate and pencil whip the bare minimum to get his check on Friday.
So the records kept getting made the old way: after the fact, from memory, close enough. Not because anyone was lazy. Because every system I built still asked the field to come to the paperwork, instead of sending the paperwork out to meet the work.
The one that almost worked
Then came the iPhone, and I built the original CrewKeeper — a timesheet app my crews carried years before “there’s an app for that” stopped being a joke.
That was the closest I ever came to getting it right. For the first time, the tool asked almost nothing of the man using it: tap your crew, tap the task, done. Almost everyone could genuinely participate — not tolerate, participate. After decades of fax machines and login pages, that alone felt like winning.
But it was ahead of its time, and it carried one flaw the technology of the day couldn’t fix: every user was on his own island. Each man’s records lived on his own phone, in his own moat. The information was finally being captured at the moment it happened — true, clean, on the spot — and then it just sat there, waiting for me to go collect it. I had solved the paperwork problem and recreated the fax machine: the field still had to send, and the office still had to wait.
Usable. Workable. Not what I was really after.
What finally stuck
The CrewKeeper on the App Store today is a ground-up rebuild, and it closes that last gap. When a foreman taps in a timesheet, the whole organization has it — live, through your own iCloud, with no server of mine in the middle. Nobody sends anything. Nobody collects anything. There is no moat; there’s one jobsite record and everyone’s standing in it. The inspection is a walk-around with your thumb. The timesheet knows the jobsite, knows who arrived, knows when. If a step can be recorded at the moment it happens, with one hand, by a guy standing on steel — it stays true, and now it’s already there.
Forty years of watching my own systems fail taught me the two things a field tool has to get right: it can ask almost nothing of the man using it, and the record has to arrive without anyone carrying it. The original CrewKeeper proved the first. This one finally delivers both.
I didn’t get here by studying contractors. I got here by being one, and by burning three decades on every wrong version of this idea first. The fax machines, the servers, the login pages, even my own almost-right first app — all of it was tuition.
CrewKeeper is what I got for it. It’s on the App Store now, and nobody has to climb a roof to use it.
— Dean Davids, Tailgate Technology