Aligning Commissions to

Scale Priority Segments

The Client:

A US-based company with 20+ sales reps and a short sales cycle that needed clarity on the effectiveness of their sales performance

The Challenge:

Leadership struggled to answer deeper questions about rep, product, and stage-level conversions that drive the team’s efficiency and profitability

Project Achievments

Deal loss clarity

Stage-level loss reasons showed which deals fall through, where, and why, enabling targeted coaching and stronger objection handling.

Aligned incentives

Data-backed commission realignment rewarded ICP-fit opportunities and de-emphasized low-quality volume, steering reps toward the segments leadership wanted to grow.

Weekly GTM visibility

Auto-delivered dashboards gave leaders reliable conversion views by rep, product, industry, and company size.

This project, like most of my projects, started with an audit to see how the sales team was operating. During this process, I made the unsurprising and industry-cross revelation that this company's sales reps didn’t really care about the CRM - they had a singular focus - to sell.

With the knowledge that the sales reps would be the ones operating this machine, I attempted to build a solution to fit their needs. I wanted to create something that would actually add value to the sales team, not just satisfy their managers.

The audit surfaced broader issues beyond rep behavior: generic training that missed real gaps, heavy manual data entry, and inconsistent processes across reps.

In order to make informed decisions they needed data, and in order to get reliable data they needed an aligned sales approach and a data gathering infrastructure.

Together with sales leadership, we defined a structured pipeline with measurable, event-based, binary stage criteria. We added stage properties and automated tasks, reminders, and emails to capture context with minimal friction. After a few full-team training sessions and documented guides, adoption followed naturally.

From there, we could accumulate the data needed for rep, product, industry, and company-size conversion insights. I built a weekly dashboard with continuously refined analytics, automatically delivered to decision makers ahead of GTM meetings.

For the first time, the company gained in-pipeline conversion visibility - revealing where deals fell off and why. Previously, managers mainly saw who closed the most; now they could judge the quantity and quality of each rep’s pipeline and coach with confidence.


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Interested in finding the best commission structure for scale enablement?

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Scale Enablement Focused CRM Migration