When my company first subscribed to HubSpot, it wasn’t my idea.
What I didn’t realize at the time was that this decision would quietly reshape how we ran the business - not just how we sold.
We were a 30-year-old company with a three-person sales and marketing team: one marketer and two salespeople. They were very clear about one thing: We needed a better way to manage outreach and business development.
They were right.
But I was also very comfortable doing things the way we’d always done them.
Despite delivering tech-forward solutions to our clients, our own internal systems had always taken a back seat.
Business development lived in:
It wasn’t elegant, but it worked. Or at least it felt like it worked.
Like many mid-market business owners, I had a deeply ingrained bias: Invest in client-facing deliverables first. Internal systems can wait.
CRM software felt like a “nice to have,” not mission-critical infrastructure.
To their credit, my sales and marketing team didn’t just ask for a tool. They built a real case.
They talked about:
They landed on HubSpot.
I agreed. Reluctantly.
Here’s the part that still makes me smile.
I was too cheap (and too naive) to invest in formal onboarding.
I assumed:
So we skipped it.
Instead, my team worked directly with HubSpot, learning as much as one marketer and two salespeople reasonably could on their own.
And they loved it.
They were energized. Genuinely excited.
They showed me dashboards.
They asked me to log in.
They encouraged me to “poke around.”
I refused.
Not because I didn’t support them, but because I was running a growing company and had zero interest in learning another piece of software.
From my perspective:
All I wanted to see was one thing: increasing sales numbers.
Sales did increase.
Outreach improved.
Follow-up became more consistent.
The team was more organized.
So from where I sat, HubSpot was doing exactly what it needed to do without requiring anything from me.
I was glad they loved it.
I was glad it was working.
And I was very happy to stay out of it.
What I didn’t understand at the time was this: Revenue can grow while operational risk quietly compounds in the background. A CRM is not just a sales tool. It is operational infrastructure.
And when leadership treats it as “their system” instead of “our system,” something subtle but important starts to form: silos.
In hindsight, those first couple of years set the stage for everything that came later, both the growth and the hard lessons.
At the time, I thought I was being practical:
What I didn’t yet see was how central HubSpot would become and how much ownership leadership would ultimately need to take.
That realization didn’t happen overnight
But it changed everything.
In Part 2, I’ll share the moment HubSpot stopped feeling like a sales tool and started behaving like something much bigger and much more fragile.
If you’re a business owner who once said, “I don’t have time to learn another system,” you may recognize yourself in that turning point.