Sales Pipeline Re-Architecture
Redesigned HeadLight's Salesforce sales process from scratch to support a tripling sales team — rebuilding opportunity stages, reports, dashboards, and data entry standards to give leadership reliable pipeline visibility for the first time.
HeadLight's sales team tripled in headcount within a year. The Salesforce org they were working in was not built for that — and it showed. Leadership couldn't trust the pipeline numbers, quota tracking happened in spreadsheets, and no one could say with confidence where any given deal actually stood.
The Problem
The core issue wasn't volume — it was that the Opportunity stages in Salesforce didn't reflect how the sales team actually worked. Without stages that mapped to real leading and lagging indicators, rep activity couldn't translate into pipeline visibility. Deals were being marked in whatever stage felt closest, which made the data directionally useless for forecasting or quota management.
What I Built
I ran discovery with the sales team and leadership to map the actual sales motion: what signals indicated real progress, what defined a stalled deal versus a closed-won, what leadership needed to make quota and budget decisions. From that, I redesigned the stage model to reflect real milestones rather than approximate ones.
On top of the restructured process: validation rules to enforce data standards at key stage transitions, a reporting layer rebuilt around the new model, and dashboards that surfaced pipeline health in the format leadership needed. I trained the sales team on the new process — not just the new fields.
Outcome
Leadership got reliable pipeline reporting for the first time. Forecasting became predictable enough to inform budget decisions, and adoption was high enough that shadow spreadsheets disappeared. All of this happened while the team was actively growing, which meant the architecture had to work for the team they were becoming — not just the team they were when I started.