The Costly Mistakes I Made in My First CRM Onboarding (And How to Avoid Them)
The Day I Knew We Needed a CRM
My boss had never even heard of a CRM before, and he resisted the idea from day one. Our “system” was entirely subjective.
One day, on a company-wide call, he declared that a certain colleague was the top salesperson in the company.
I knew there was no way that was true.
I became obsessed with proving it through tangible data—something our current way of working simply couldn’t provide. That’s when my two-year odyssey to find the right CRM began.
My Four Non-Negotiables for Choosing a CRM
I wasn’t going into this blind. I had a very specific set of needs:
Multi-Client Structure
We were a multi-client brokerage—one company managing multiple sub-companies. I needed to ensure the CRM would let us act on behalf of each client and maintain privacy in reporting.
Revenue Tracking
We needed to track not just sales, but commission by client and customer. Brand A, Brand B, and Brand C needed to roll up into one dataset, and each customer needed to be assigned to a rep/territory. Bonus: the ability to log POs and start predicting cash flow.
Ease of Use
If it was clunky, with a broken user interface and too many manual steps, no one would use it. Integration with email was a must. A monkey needed to be able to operate this thing.
Executive Dashboards & Client Reporting
I needed tools to give managers real insight and clients clear visibility into our activity—especially because in brokerages, reps are often working hard in the field without directly communicating with every client.
The CRM Sales Pitch Problem
I started with five CRM demos, asking each vendor the same set of questions.
Every. Single. One. told me they could meet our needs. My gut told me otherwise—what we needed was complex, and I doubted most of them could deliver.
My boss slowly warmed up to the idea, joining calls and asking for specific examples of how the system would work for us. None could really prove it.
We interviewed about 15 more CRMs. Finally, we found one that could do exactly what we needed—at a price so astronomical it was in a neighboring city to our budget.
Two Years Later… and a Setback
The process dragged on for two years. Somewhere in that stretch, I was written up for the first time in my career. I was pushing too hard for change, and my frustration was showing.
I backed away. I stopped caring.
Then one fall, we lost four clients in two weeks—including one “A-potential” account worth millions. The stakes were now undeniable.
The Twist No One Saw Coming
When we finally had a system in place and the numbers came through, the truth was impossible to ignore.
Our “top salesperson”? The one my boss championed? He wasn’t just not number one—he was dead last in revenue. Smooth talk, great perception, but the lowest actual contribution to the company.
And me? I was at the top.
That moment cemented my belief in data-driven sales operations: without a CRM built and implemented the right way, you’re managing on perception, not reality.
Lessons I Carry Into Every CRM Project Today
That experience taught me what most companies get wrong about CRM onboarding:
Believing software alone will fix a broken process
Choosing a tool without mapping actual workflows and data needs
Underestimating the importance of user adoption and simplicity
Ignoring the cost of wrong or missing data
It’s why I now help $1–10M companies implement CRMs with structure, clarity, and the right processes from day one—so they can trust the data and make better decisions.
Before You Choose Your CRM…
If you’re about to onboard a new CRM or rebuild your current one, don’t leave it to guesswork. Start with a RevOps Audit to uncover exactly what you need—and what to avoid.
It’s the fastest way to skip the two-year detour I lived through and launch a system your team will actually use.
