[agentultra]

If you don't care, I can't help change your mind.

I took a small company that was living contract to contract into a world where they started making millions in annual recurring revenue.

There's no secret, magic bullet. All I did was make sure we were delivering progress at a regular cadence. Kept communication channels open. And tried to, but ultimately failed at, training the sales team to stop with the secret deadline negotiation.

I understand the sales cycle at the enterprise SaaS level is a long song-and-dance of promises and and punishments. I understand that money only changes hands when the customer feels like they will get their money's worth or else your business will go out of existence. It's a difficult game to play.

However... they were never unhappy. Steady, reliable, and consistent beat out guessing, promising, and hoping to deliver every time. The dollars proved it.

[Hasu]

I think we're talking past each other.

> I took a small company that was living contract to contract into a world where they started making millions in annual recurring revenue.

> There's no secret, magic bullet. All I did was make sure we were delivering progress at a regular cadence. Kept communication channels open. And tried to, but ultimately failed at, training the sales team to stop with the secret deadline negotiation

This is what I call hitting deadlines.

[agentultra]

> I think we're talking past each other.

Perhaps. I'm not saying that deadlines don't exist or shouldn't. I am saying that they're often unnecessary and most software teams can deliver value without them.

If you're in the embedded space there's no dodging deadlines. If you need to flash ROMs it could be months before you can do a release if you miss your deadline. You might not have enough money to survive until then.

If you're shipping boring, line-of-business enterprise SaaS you don't need deadlines. Customers want software that solves their problems and are happy with something that works for 80% and a steady rate of improvements over time. They want progress and milestones. There's nothing wrong with taking an extra week or month to reach the next milestone.

Where you get the "deadlines equal dollars," mentality in enterprise software is from the long sales cycle with the big price tags. A business is going to have reservations about dropping a few hundred thousand on a new software product. And so you end up with these negotiations between sales, management, and the software teams where you're lying about the deadlines to different parties in order to keep everything in line. I don't think that's a good way to go about it.

Especially when most of the time it's not even necessary. This was the finer point I was often finding myself in opposition to the sales folks with. Their reality was that deadlines are a negotiating chip they can't ignore. The software developers' reality was that any estimate about a deadline is completely made up of hopes, dreams, and unicorns. The easiest way to get people to work together, in my opinion and experience, is to cut out the lying and just be honest.

Some organizations like that, some don't. I went back into being an IC because I just can't operate at that level and keep my sanity/energy.