“When you're clear on how your business operates, the software piece becomes easy."
Joe Sandin, President of Onsharp, recently shared this nugget of wisdom on the RevOps Champions podcast, and by doing so, articulated something we’ve observed, too: CRM projects don’t fail because of bad tools. They fail because the business behind the tools isn’t aligned.
Sandin continued...
“You're not trying to invent yourself at the same time as implementing a piece of software.”
Sandin's point hit home for me, because we’ve lived through exactly what happens when the opposite is true.
About a year ago, we hit pause to reflect on our CRM implementation projects: which ones delivered real traction—and which ones felt more like pushing a boulder uphill.
It wasn’t about the tools or the timelines. We had those in place across the board.
The biggest difference?
Whether the organization had taken the time to document and align on how it actually works. Most hadn’t.
They were trying to implement clarity through software—when what they needed was operational clarity first.
When that clarity was missing, we saw some familiar symptoms:
- Projects veering off timeline and budget
- Lower-than-usual user adoption
- Change management that struggled to take root
So we asked ourselves: What’s really changed?
Turns out—quite a bit:
- HubSpot has become more powerful (and more complex)
- Our clients have grown—from SMBs to mid-market organizations
- Their businesses are more intricate: more people, more systems, more moving parts
We were a bit like the proverbial boiling frog—adapting to rising complexity without stepping back to re-evaluate our own structure and methods.
In the past, one sharp “HubSpot ninja” could lead an entire implementation. But in 2025? That’s just not realistic.
A modern CRM transformation actually takes an experienced team of:
- Project managers
- Change management leads
- Data and reporting analysts
- Trainers and enablement experts
- Strategic consultants
- Platform specialists—across HubSpot and the broader tech stack
CRM isn’t “just software” anymore.
It’s a transformation initiative. And as Joe put it, you can’t build the plane while you’re flying it.
The path to success starts with clarity—before a single tool gets configured.
So, we took our own advice.
- We evolved our team structure.
- We reimagined our processes—before reworking them in any system.
- And next, we’ll “re-implement” our own project management platform to support that evolution.
Here’s my takeaway for all of us leading through complexity:
The tools we choose matter. But how our business thinks and operates matters more.
When we take a step back and get clear on our internal processes—how our teams collaborate, how our data flows, how we make decisions—everything else starts to click.
🌟 Technology becomes a catalyst, not a blocker.
🌟 Our teams feel empowered, not overwhelmed.
🌟 And change becomes something we lead with confidence—instead of reacting to with stress.
This kind of work doesn’t just lead to better implementations.
It unlocks a smarter, stronger, more scalable version of the business.
If you're leading a team through change—or gearing up for what’s next—here’s your reminder:
🛫 You don’t have to fly the plane while building it.
Pause. Align. Then take off with clarity and confidence.
(As someone who loves to move fast, I’m reminding myself of this too.)
Here’s to building better businesses, together. 👩🏻🤝👨🏽
Cheers,
Kristin
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Kristin Dennewill
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