In Brief

Before the full read, here’s the short version I’d share with another pricing leader over coffee:

• Pricing software succeeds or fails based on people, structure, and alignment—not features. Technology only amplifies what’s already there.
• Organizations get more value by following a realistic maturity curve than by rushing to advanced tools too early.
• Sales adoption improves when pricing systems protect autonomy while reinforcing profitable behavior.
• Clean, governed data enables better decisions—but waiting for perfection delays real impact.
• Sustainable pricing change depends as much on change management and education as it does on system configuration.

Over the past several years, I’ve led pricing software implementations at multibillion-dollar distribution companies. Each one taught me something different. But the biggest lesson showed up again and again:

Software doesn’t solve problems. People do.

Early on, I thought the right platform would do more of the heavy lifting. That once the system was live, better pricing behavior would naturally follow. What we learned—sometimes the hard way—is that technology only amplifies what’s already there. Clear structure gets stronger. Misalignment shows up faster.

That’s why the gap between successful pricing implementations and stalled ones rarely comes down to features. It comes down to readiness.

Here are the lessons that stuck with me most.

Lesson 1: Don’t jump ahead of your maturity

You can’t go from spreadsheets to AI any more than you can crawl straight into the Olympics.

Every successful implementation we’ve seen followed a maturity curve:

Crawl → Walk → Run → Optimize → Automate → AI

Each phase delivers value on its own. The trouble starts when teams skip the muscle-building required for the next step. We’ve watched organizations invest in advanced tools before governance, training, or decision clarity were in place—and then wonder why adoption stalled.

Pricing transformations work best when they respect where the organization actually is, not where leadership wishes it were.

Lesson 2: Prioritize structure before software

One of the most common mistakes we’ve seen is starting an implementation without a clear organizational foundation.

Pricing touches sales, finance, operations, IT, legal, and compliance. If ownership and decision rights aren’t defined up front, the software becomes a battleground instead of a tool.

When structure is clear, alignment follows more naturally. When it isn’t, every configuration choice turns into a negotiation. The system may still go live—but it won’t stick.

Lesson 3: Build buy-in early, and keep building it

Buy-in isn’t a kickoff meeting. It’s an ongoing process.

In one implementation, sales raised a concern almost immediately:

“Are we going to need approval for every price change now?”

That wasn’t resistance. It was experience.

They’d lived through rigid systems that slowed deals and stripped autonomy. If we had ignored that concern, adoption would have suffered from day one. Instead, we redesigned. We built self-service tools with guardrails—enough freedom to move quickly, enough protection to preserve margin.

That single decision changed everything. Sales felt supported instead of policed. Trust followed. Usage followed.

Pricing has to flex to different perspectives if change is going to last.

Lesson 4: Clean data is nonnegotiable—but perfection isn’t

During one implementation, we discovered contracts everywhere. Shared drives. Email inboxes. Personal folders. Even the trunk of a sales associate’s car.

That was the moment it clicked: pricing wasn’t broken because people didn’t care. It was broken because institutional knowledge had nowhere to live.

Centralizing and governing that data wasn’t glamorous work, but it was essential. At the same time, we learned not to let the pursuit of perfect data halt progress.

Good enough to launch beats perfect but never live.

Clean what you can. Launch. Improve continuously.

Lesson 5: Not everything can—or should—be automated

Most of the business will follow clear rules. Some agreements won’t.

We’ve seen customer contracts that were simply too complex to automate without risking relationships. Early on, that’s okay—as long as exceptions stay exceptions.

In those cases, we built white-glove processes with manual oversight. Not as a permanent solution, but as a bridge. Over time, those contracts could be simplified and brought into the system naturally.

Automation should accelerate the majority, not break trust over edge cases.

Lesson 6: Change management matters as much as configuration

System change is easy compared to behavior change.

People need to understand not just how pricing is changing, but why. We spent as much time talking about mindset shifts as we did system features.

After go-live, we kept feedback loops open through regular focus groups. That’s where we learned what was actually working, what wasn’t, and what needed refinement.

Those conversations did more for adoption than any training deck ever could.

Lesson 7: Teach the financial impact—patiently

Reps make pricing decisions every day. Helping them understand the financial impact of those decisions took longer than we expected.

We focused on contribution margin because it reflects reality—what’s left after freight, service, returns, and complexity. That shift didn’t happen overnight. It required repetition, real examples, and a lot of dialogue.

But once it landed, conversations changed. Pricing stopped feeling like a tug-of-war between departments and started feeling like a shared responsibility.

Lesson 8: Align with the IT roadmap

Timing matters more than most teams expect.

If IT is already rolling out a major system—CRM, ERP, anything enterprise-wide—splitting attention rarely ends well. We learned to pause when needed, sequence initiatives thoughtfully, and protect trust across teams.

Flexibility kept projects moving forward instead of burning people out.

A Closing Thought

None of these lessons came from theory. They came from sitting in the tension between what the business wanted and what the organization was ready for.

Pricing software can move the P&L quickly—but only when people trust it, understand it, and see themselves reflected in how it works.

If you’re leading a pricing change, don’t rush past the human work. Get the structure right. Earn alignment. Teach patiently.

The technology will do its job once the organization is ready to let it.

If any of this sounds familiar, it’s because most pricing leaders are navigating the same tradeoffs—often quietly, and often under pressure.

We spend a lot of time comparing notes with peers who are in the middle of pricing change. If you’re wrestling with readiness, adoption, or sequencing and want to pressure-test your approach with people who’ve been in the seat, we’re always open to that conversation.