I’ve spent the last year trying to figure out why automation still feels broken — even when it’s working exactly as designed.
Triggers fire. Sequences run. Messages go out on time. On paper, everything is functioning. But in practice, automated communication often feels disconnected, mistimed, or oddly unaware of what’s actually happening.
That gap isn’t caused by a lack of tools. It’s caused by a lack of context.
Most automation systems are built around rules, not understanding. Something happens, so something gets sent. There’s no awareness of why the event occurred, what came before it, or whether the message still makes sense in the larger story.
That distinction matters more than most teams realize.
Why Rules Alone Don’t Scale Relationships
Rules are binary. Either a condition is met or it isn’t. But real business interactions don’t work that way.
A lead fills out a form after a sales call, not before it. A customer opens an email while already deep in a buying process. A follow-up arrives after the decision has been made — just not in your system.
When automation ignores those realities, communication becomes noise. It may still get opened. It may still technically “perform.” But it stops feeling intentional. At scale, that’s costly. Not just in unsubscribe rates, but in trust.
Context Changes Everything
Context-aware automation behaves differently. It doesn’t ask, “Did this event happen?” It asks, “What does this event mean?” That shift requires seeing more than one data point at a time. It means understanding engagement history, sales activity, timing, and intent — and using that broader picture to decide whether a message should be sent at all.
AI doesn’t fix this by default. Most AI in email tools is just a faster way to send the wrong message. The problem was never speed. It was awareness.
Fragmented Systems Can’t See the Whole Story
I’ve watched this firsthand. CRM data in one tab. Email platform in another. Sales notes in a third. Each system confident it’s doing its job, none of them aware of the others.
When systems can’t see the whole story, automation can’t act intelligently.
Bringing those signals together — behavior, engagement, timing, and outcomes — is the difference between automation that executes and automation that understands.
What I’m Building Toward
This is the gap I’ve been thinking about for the last year. Not smarter emails. Not cleverer sequences. Better decisions.
At LeadMachine.fyi, I’m designing automation around shared context — not just email triggers. The goal isn’t to send more messages. It’s to surface the right action at the right moment, based on what’s actually happening across a business, not just inside an inbox.
When automation understands context, it stops feeling automated. It starts feeling considered.
That’s the direction I’m pushing — both in how I think about systems and in what I’m building.
Because communication doesn’t break when tools fail. It breaks when understanding is missing.
~jt
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