
How Simplifying My Tech Stack Reduced My Software Costs (and Finally Made My Business Feel Coherent)
February 20, 2026If you had told eleven-year-old me that I would one day be a fractional CMO, hold ownership stakes in multiple companies, advise founders on growth and strategy, lead marketing teams, produce large-scale digital events, and spend my days thinking about systems, psychology, and leverage, I would have laughed directly in your face.
Not politely.
Not modestly.
Out loud, probably while standing in a gas station parking lot with a paintbrush in my hand, trying not to drip white paint onto freshly poured asphalt.
Because that is where this story actually starts.
Not with a vision board.
Not with a carefully plotted career path.
Not even with a marketing degree.
It started with curb painting, garbage pickup, bathroom cleaning, snow shovelling before and after school, and learning very early that work was not something you avoided — it was something you showed up for, even when it was uncomfortable, boring, or deeply unglamorous.
The First Lesson I Didn’t Know I Was Learning Yet
I was eleven years old when I started working at my parents’ gas station.
Every Saturday.
Eight in the morning until four in the afternoon.
No sleeping in. No excuses.
Summers were longer. Winters were colder. And if it snowed, it didn’t matter how early it was — you were outside dealing with it.
My parents were tough in the way that only people running a family business can be, but they were also fair. They believed in contributing, pulling your weight, and understanding that effort mattered long before titles did.
At the time, the lesson felt simple: show up and do the work.
Looking back, it was something much bigger.
If you want security, you create value that’s hard to ignore.
I didn’t have language for that yet. I just knew that when things needed doing, I did them.
The Costco Years, or How I Made Myself Un-Firable on Purpose
Fast forward to university.
The gas station chapter had ended.
Money was tight.
Tuition was very real.
I applied to Costco Wholesale before the warehouse near my house had even been built, which is not a metaphor — the building literally did not exist yet. When I was hired, part of my early “training” involved helping with landscaping and prep before opening day.
I was seasonal.
Part-time.
Entirely expendable.
And I made a very conscious decision early on that if they were cutting people after the seasonal period, it was not going to be me.
So I cross-trained. Everywhere.
Front end. Bakery. Deli. Meat department. Receiving. Sales audit. Vault. Accounts payable and receivable. RTVs. Merchandising. Cart pushing in the rain with plastic bags stuffed into my running shoes so my feet wouldn’t soak through before my shift ended.
If no one wanted the job, I took it.
If it was inconvenient, I learned it.
If it made me useful, I leaned in.
I wasn’t trying to climb a ladder. I was trying to become essential.
That instinct — to solve the problem no one else wanted to touch — would quietly follow me for the rest of my career.
The Pattern That Changed Everything
About five years in, I needed a minor medical procedure, which meant I was put on modified duties for a few weeks.
Management parked me in a freezing back office with stacks of printed reports and a phone.
My job was simple and soul-crushing: call expired members and ask if they wanted to renew.
It was boring. Repetitive. Easy to phone in.
Until my brain did the thing it has always done — it started noticing patterns.
Names were repeating. A lot.
People weren’t actually lapsing. They were cancelling and re-signing every year to take advantage of a sign-up perk. Which meant retention numbers were off, marketing data was skewed, and warehouses were losing budget because their membership base looked smaller than it actually was.
That tiny loophole was quietly costing the company real money.
So I flagged it.
With the help of a marketing leader who saw potential instead of hierarchy, we rebuilt the system, closed the loophole, corrected the data, and rolled the fix out more broadly.
It saved my warehouse thousands.
Then it saved the company millions.
I also uncovered a fraudster gaming the numbers — someone who had just won a prestigious internal marketing award.
That irony still makes me laugh.
That moment changed my trajectory overnight.
From English Major to Marketing Supervisor
Somewhere along the way, the liberal arts girl with an English degree became a marketing supervisor.
I ran teams.
Managed budgets.
Opened and closed warehouses.
Trained staff.
Oversaw campaigns.
Made sure the numbers actually meant something.
And that’s when marketing clicked for me.
Not the shiny parts, although I do enjoy those too.
The systems.
The psychology.
The behaviour patterns.
Why people do what they do.
Why messaging works or doesn’t.
How small operational changes create outsized results.
Marketing, at its best, isn’t about noise. It’s about clarity.
The Gold Mining Plot Twist
After nearly fifteen years, I needed a new challenge, so I moved into corporate communications and investor relations for two global gold-mining companies.
Different world.
Different pressure.
Much higher stakes.
I learned crisis communications, speech writing, investor messaging, and in-person event planning at a level that leaves no room for fluff. I helped build an internal communications program that won a Golden Quill Award from the International Association of Business Communicators.
It was intense. It was fascinating.
And after four years, I knew two things with absolute certainty:
I was very good at translating complexity into clarity.
I did not want to spend my life doing it in boardrooms.
The Leap (No Plan, Just a Strong Gut Feeling)
So I left.
No backup plan.
No shiny safety net.
Just a very strong sense that I was meant to build something of my own.
This was early digital business — pre-Zoom, barely Skype, when being a virtual assistant still required explanation.
I learned everything I could: VA work, project management, launch strategy, copywriting, and client delivery.
Then one day, a client casually asked, “Can you help me build a virtual summit?”
That question changed everything. Again.
From Tasks to Strategy
One summit turned into dozens.
Dozens turned into hundreds of webinars.
Then consulting.
Then, a full-scale marketing strategy.
I stopped being the person who executed tasks and became the person who made things work.
That’s how It All Works was born with my partner Jason. Alongside my podcast Acquire, fractional CMO work, and collaborations with companies doing genuinely meaningful work in healthcare, media, and education.
I’ve helped generate millions in revenue, build systems that scale, and lead marketing for businesses that actually matter.
And I still think about those curbs.
What All of This Taught Me
Every phase left its mark.
Do every job once — it builds empathy and sharper strategy.
Look for patterns others miss — that’s where leverage lives.
Solve real problems — that’s how you become indispensable.
Let go to grow — every pivot requires releasing an old identity.
Systems are not boring — they turn chaos into clarity.
Where I Am Now
These days, I split my time between fractional CMO work, agency leadership, my podcast, speaking, and writing my first book, coming in 2026.
And honestly?
It still blows my mind that all of this started with a paintbrush and a curb.
The Thread That Ties It All Together
Here’s the real lesson.
Nothing you learn is wasted.
Every skill stacks.
Every “crap job” teaches you something.
Every detour matters.
I didn’t plan on becoming a marketer.
But every step pointed me here.
And if you’re somewhere between where you started and where you think you should be, keep going.
You never know which overlooked task, side job, or uncomfortable yes is about to rewrite your entire story.
I'm Jennie, and trust me, I've been where you are.
You’re trying to scale your business, and it’s not just about growth, right? It’s about finding those clever tweaks and big moves that really pay off. It’s about knowing which lever to pull and when. I get it because I’ve been through that maze too. That’s exactly why I started my business.
I wanted to create a place where driven folks like us could get our hands on the strategies that make a real difference. I’m all about sharing the insider secrets, the ones that help you scale smart and keep your business steady while you climb.
I believe that it’s not just about tips and tricks. I’m your guide, your support, and your biggest fan, all rolled into one. I’m here to show you the ropes, so you can make those bold moves and watch your business soar.
Ready to take the leap? I’ve got your back.
The Benefits of a Fractional CMO
More Bang for Your Buck
Life’s all about change, especially in business, and a fractional CMO’s got the agility to switch gears fast to keep your strategy fresh and focused.
Ready to Pivot at a Moment’s Notice
With a fractional CMO, you’re tapping into a goldmine of know-how from all kinds of industries – they’ve seen it all and know what sticks.
Treasure Trove of Tricks from Every Trade
With a fractional CMO, you’re tapping into a goldmine of know-how from all kinds of industries – they’ve seen it all and know what sticks.
Fast-Track Your Growth
A fractional CMO is like a boost button for your business, spotting opportunities and setting them in motion quicker than you can say ‘scale up’.
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