Melissa Cutler Fractional CMO and Revenue Architect

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Melissa Cutler Fractional CMO and Revenue Architect Fractional CMO & CRO
⚙️AI Systems Architect
🧠 Turning Emotionally Intelligent Marketing Into Revenue

I went into a client project thinking I was building an Instagram booking flow.The first version of the problem was pret...
09/21/2026

I went into a client project thinking I was building an Instagram booking flow.

The first version of the problem was pretty straightforward: someone shows interest, gets workshop dates in a DM, chooses one and registers.

Then we followed what had to happen next.

The date still had to be available when they actually booked. The CRM needed to recognize the person without creating duplicates. Calendar invitations, confirmation emails and reminders had to stay accurate if the booking changed. Support needed somewhere to go. And eventually the business needed to know whether that original Instagram interaction led to attendance, a sales conversation or revenue.

Somewhere in the middle, the project stopped feeling like a chatbot.

It had become a question of whether the business could follow a customer from first interest to commercial outcome without losing the thread.

If you have active marketing already, you may know this feeling. Nothing looks completely broken. Ads are running. Content is going out. There is a CRM. People are following up.

But ask what happened to one specific enquiry, and suddenly the answer lives across three tools and two people.

That is where this project ended up: making that path clear enough that when something slips, you actually know where to look.

I accidentally ran a better test of my Content Agent before I even got on stage.I was at an AI x Creativity event to dem...
08/30/2026

I accidentally ran a better test of my Content Agent before I even got on stage.

I was at an AI x Creativity event to demo AI UGC. Before it started, I got talking with Aaron. He described himself as pretty low-tech and was trying to figure out where AI might actually be useful to him.

A few minutes in, I asked if I could record us.

“This can become my content for tomorrow.”

Not an interview. Just a conversation I was already having.

Later, I gave the recording to the system.

It separated who said what, kept uncertain parts uncertain, compared it against what I’d already talked about, and surfaced what was actually new.

The conversation became the test.

I don’t have a shortage of source. It’s already in client calls, events, voice notes, random conversations, or while I’m actually doing the work.

What I want is to stop losing the useful parts in between.

Someone recently gave me a better phrase for the life I’m trying to build:

work-life integration.

To me, work-life balance sounds like work and life are two separate things competing for space.

Integration feels more like one life where they can feed each other without every useful moment becoming another admin task.

That’s much closer to me. 😂

The conversation can become source. Something I learn over dinner can change a decision next week. The event can feed the work, and the work can open the next room.

That made Aaron being “low-tech” even more interesting.

The value wasn’t in him becoming more technical. It was in the technology disappearing further into the background.

That’s the version of AI I’m building toward:

Not more content for the sake of content.

Simply put: I want to just live my life and have everything fall into place.

I kind of just show up places and then things fall into place.I was leaving Builders Club and ran into Prabal. I’d meant...
08/27/2026

I kind of just show up places and then things fall into place.

I was leaving Builders Club and ran into Prabal. I’d meant to help with one of his previous events, so I asked:

“Do you need help with Thursday?”

Nope. All good.

“Do you have all your speakers?”

Actually… no.

They were still looking for people to demo creative AI, so I kept asking questions. What are people interested in? What are they struggling with? What would actually be useful to show?

UGC came up. That familiar:

“Why does it never come out how I want it to?”

I know that feeling very well. 😂

A few questions later, I’m speaking tonight.

But I don’t want to put a beautiful AI image on a screen and go:

“Look what AI can do.”

Okay…but how did you get there?

So I’m testing the same idea three ways:

1. Start with only a prompt.
2. Add references.
3. Start with a real image and build from there.

What I’m interested in isn’t which one makes the prettiest picture. It’s what happens to control as the quality of the source changes.

Because:

“Make me good UGC”

is very different from:

“Make this look like me, feel like me, communicate what I actually mean, and still look like somebody took the photo.”

That’s what I want people to leave with tonight. Not just a prompt.

A better understanding of what information helps the machine understand what you actually mean.

So yeah. I offered to help with an event, and somehow that turned into getting to share something I’ve been learning with a room full of builders.

Which feels pretty full-circle, considering how much of this I learned because people in my own circle were willing to share what they knew with me.

Register for free at the AI x Creative Luma Event Link:
https://luma.com/jt6witdi?tk=Hih5mU
📍Builder’s Club, 165 King St W, Kitchener, ON
📆 Thursday, August 27th @ 6pm-10pm
PS: There will be networking and pizza 🍕

The annoying thing about building one system that works is:You still don’t know if you built a system.Or a very elaborat...
08/27/2026

The annoying thing about building one system that works is:

You still don’t know if you built a system.

Or a very elaborate coincidence.

So I kept going.

I’ve now rebuilt the same underlying architecture across different businesses, different source material, and different jobs.

Two have been tested and are working well.

Today I’m building the fourth.

And this one is interesting because the output is completely different.

The first system was heavily used for content: articles, emails, workshop scripting, product copy, Stories.

This one needs to take messy client calls, customer conversations, old brand work, examples of what’s good and bad, current strategy, objections, voice, offer thinking…

…and turn that into the foundation for a brand kit.

Different business.
Different people.
Different source.
Different deliverable.

Same underlying architecture.

That’s the test I care about now.

Because one client working could mean I accidentally built something perfectly suited to that client.

What I want to know is:

Can I keep the reasoning structure and swap the business underneath it?

Can it understand that one business needs content today, while another needs brand voice and objection handling, and another might need help figuring out how to turn interest into high-ticket clients?

Without me rebuilding the entire brain every time.

I’m still early.

Four systems is not proof of some universal architecture.

But two working well is enough for me to stop calling the first one luck.

Now I want to see how far the pattern holds.

That’s a much more interesting test.

I’ve been quiet because I’ve been building something I didn’t really want to talk about until I could see it work.
For a...
08/26/2026

I’ve been quiet because I’ve been building something I didn’t really want to talk about until I could see it work.

For a while, I thought better AI meant more.

More context. 
More files. 
More agents. 
More automation.

Right now, I have roughly 2,486 files sitting behind what was supposed to be my client’s “second brain.”

Except every time I wanted something good out of it, I still had to explain the business, what mattered, what changed, and correct the assumptions.

Basically, I was still the middleware.

So I changed the problem.

Instead of asking:

How do I write a better prompt?

I started asking:

What context and judgment need to already exist underneath it so the human doesn’t have to carry everything every time?

That changed what I built.

I stopped trying to automate everything first.

I separated the slower stuff from what changes constantly:

Who the business is.
What’s true right now.
How I make decisions.
What happened this run.
What the customer actually said.

Then I made the interface almost stupidly simple.

We tested it on real work today.

The commands were basically:

PROCESS THIS CAPTURE
SHOW ME THE CONTENT INVENTORY
GO DEEPER ON THIS
WRITE IT

And it produced work good enough to move to the actual subject-matter expert for her pass instead of me rebuilding the strategy from scratch.

It’s not fully handoff-proven yet. I was still guiding parts of the run, and that distinction matters.

But I think this is the first time I’ve seen the thing I was trying to build.
Not a better prompt.

Not a bigger second brain.

Not an AI that magically “knows everything.”

A system where the intelligence lives far enough underneath the interface that the human can ask for what they need in normal language.

A simple prompt isn’t necessarily a less sophisticated use of AI.

Sometimes it’s evidence that the sophistication finally moved somewhere else.
I wasn’t trying to get better at prompting AI.

I was trying to build enough context and judgment underneath it that the prompt could finally become simple.

Last week, I spoke with a business owner who has run a business for 30 years.He spent $100,000 between consulting and a ...
08/05/2026

Last week, I spoke with a business owner who has run a business for 30 years.

He spent $100,000 between consulting and a custom build. They made progress, but the path kept changing. Then he found ActiveCampaign, scrapped the build, and stayed with it.

He wasn’t resistant. He was curious, willing to invest, and kept moving.
What I noticed was the order: they chose the solution before ranking the everyday problems it needed to solve.

I’ve been interviewing leaders across insurance, aerospace and defence, and brokerages because I don’t want to assume what businesses need. I’ve built and handed off custom AI systems. Now I’m listening for what is still unsolved.

One of his clearest problems was painfully small: when a client hits Reply instead of Reply All, his assistant disappears from the thread. He has to catch it and add her back inside an inbox with 37,000 unread emails.

In a business where one contract can be worth $7 million, a missed reply is not admin clutter. It can mean responding after the client has chosen someone else.

I know this pattern because I’ve built several things to 50%, 75%, or 90%, called them good enough, and moved on. The unfinished pieces kept taxing my attention.

Now, for myself and my clients, I’m taking one small, valuable problem to 100%, letting the time it frees create room for the next solve, then repeating.

I’m gathering context. If you have 15 or 30 minutes to share the tiny friction carrying expensive stakes inside your business, I’d love to listen.

More perspectives can make the solutions sharper, simpler, and easier to carry.

We don’t need to know what we’ll do with the time before we’re allowed to want it back.

04/09/2026

You’ve been throwing spaghetti for years.
�Good.�Watch this.
I don’t need a clean slate.�I need your history.
�Hot streaks. Cold streaks. All of it.�That’s where your best spaghetti recipe already lives. 🍝

For the first time in I don’t know how long
 I’m building from pleasure.Not anxiety.
 Not survival mode.
 An actual pull...
04/09/2026

For the first time in I don’t know how long
 I’m building from pleasure.

Not anxiety.
 Not survival mode.
 An actual pull toward something.

I’ve been staying up til 1 or 2am
 working on software I can barely explain.
 There are no tutorials for this.
 What the f*** are we all doing?
 We’re making it up as we go.

I’ve hit the hundred K month.
 Felt nothing.

It’s the build. The ride.
 The problems nobody has solved yet.

I’ve been recording everything for over a year.
 Voice notes. Calls. Reflections.
 I didn’t know what I was recording for.
 Now I do.

The four minute mile I have my sights set on
 is self-optimizing businesses.
 I’m not saying that’s close.
 I’m saying that’s the direction.

I consider myself an explorer more than anything else.
 It just so happens the outputs are useful for businesses.

I got these words I like from Alex Hormozi:
“Never let go of the goal.
Let go of the timeline.”

Most people call it a funnel.I call it a revenue system.
 Because a funnel implies one direction.
 And what actually dri...
04/09/2026

Most people call it a funnel.

I call it a revenue system.
 Because a funnel implies one direction.
 And what actually drives sales
 is never just one thing.

It’s the DM conversation.
 The content that was live
 the week those leads came in.
 The email sequence running in the background.
 The AI bot - saying the right thing
 or the wrong thing
 at exactly the wrong moment.

All of it together.
 Reading human behaviour across every touchpoint.

Not a dashboard.
 A zoom in and a zoom out mirror
 on what’s actually happening.

One client. New city. No traction.
 $3,700 her second month.
 Stopped discounting.
 People driving an hour to see her.

That’s the revenue system.

Address

Waterloo, ON
N2J, N2K, N2L, N2T, N2V

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