Convert · Operate
Lead Sherpa
One deal, one payment: revenue operations rebuilt into a single source of truth
PeopleFinders runs a portfolio of real-estate data brands — PropertyReach and Lead Sherpa among them — billing thousands of subscribers through Chargebee and managing the funnel in HubSpot. But the two systems didn't tell a straight story: deals logged inflated contract values instead of actual cash collected, subscription revenue was tangled together with platform and wallet fees, and billing data reached the CRM through a fragile middle-layer sync that introduced errors. Leadership had no clean line of sight from pipeline to revenue. The Matchbox ran a full systems audit, rebuilt the deal architecture and billing integration from first principles, cleaned the underlying data, and consolidated two brands into a single operating model — turning a tangle of disconnected tools into one trustworthy source of truth.
one deal equals one real payment
brands consolidated into one HubSpot data model
MRR visibility by brand and segment
Key achievements
Rebuilt PeopleFinders' deal architecture into a single, payment-triggered subscriptions pipeline.
Replaced an error-prone middle-layer billing sync with a direct Chargebee-to-HubSpot integration.
Delivered real-time MRR visibility by brand and segment through a rebuilt reporting model.
Consolidated two brands into one unified HubSpot data model through a phased migration.
Deal Architecture Rebuild
Making Every Deal Mean One Real Payment
Deals that didn’t reflect the money.
The Challenge:
HubSpot’s deals were effectively unusable for reporting. Deal amounts were inflated — logging total contract value rather than the cash actually collected — annual plans pulled through incorrectly, and subscription revenue was conflated with platform and wallet fees. There was no clean line from pipeline to revenue, and MRR carried no real context.
The Matchbox Solution
We rebuilt the deal model around a single principle — one deal equals one payment — so every record maps to real cash collected.
- Created a clean Subscriptions pipeline with minimal stages: Payment Received (Closed Won) and Payment Reversed/Refunded (Closed Lost).
- Redefined deal amount as the incremental cash collected — the change in Total Amount Paid — with MRR captured as a snapshot at time of payment.
- Set a payment-triggered deal-creation rule (triggered by a rise in Total Amount Paid, not billing dates or status alone).
- Added the subscription properties needed for lifecycle reporting: Original Brand, Payment Number (sequential, for tenure), First Product, Upsell Path, and Cross-sell Date.
Billing Integration Cleanup
Straightening the Line Between Billing and the CRM
A fragile sync in the middle.
The Challenge:
Chargebee reached HubSpot through a middle-layer database sync that introduced latency and errors, and deal amounts pulled incorrectly for annual plans. The indirect path made the billing-to-CRM data flow unreliable — and impossible to fully trust for revenue reporting.
The Matchbox Solution
We mapped the existing data flow, isolated the failure points, and moved toward a direct, reliable integration.
- Evaluated a direct Chargebee → HubSpot integration to bypass the error-prone middle-layer sync.
- Defined the exact deal-creation trigger (a Total Amount Paid delta) to stop annual-plan miscalculations.
- Set a clear division of labor: operational, real-time metrics in HubSpot; complex executive reporting in Power BI.
- Documented the known limitation (totals-only sync) so reporting stayed honest about what the data could and couldn’t show.
Data Hygiene & Reporting
Turning Clean Data Into Real-Time Visibility
Good decisions need trustworthy numbers.
The Challenge:
The account had accumulated redundant and test fields, inconsistent naming, and no way to see MRR by brand or segment. Conversion definitions weren’t aligned across brands, and contacts created through integrations lost their original-source attribution — so funnel reporting couldn’t be trusted.
The Matchbox Solution
We cleaned the foundation, then built the reporting layer on top of it.
- Cleaned up and merged redundant and test fields and standardized naming conventions across the account.
- Added an Original Brand field and a PQL field to make funnel reporting possible across both brands.
- Built a HubSpot dashboard for MRR by brand and segment for real-time business visibility.
- Built cross-sell and upsell automation workflows to act on the newly reliable data.
- Aligned conversion definitions across brands so funnel metrics finally meant the same thing everywhere.
Brand Consolidation
One Data Model Across Two Brands
Two brands, two sources of truth.
The Challenge:
Lead Sherpa and PropertyReach ran on separate, duplicative HubSpot structures, which meant divergent stages, duplicated effort, and no unified view of the combined business as the two products converged.
The Matchbox Solution
We unified the two brands onto a single operating model through a phased plan designed to avoid disruption.
- Unified deal stages and the underlying data model across both brands.
- Consolidated Lead Sherpa into PropertyReach in HubSpot and updated all branded assets.
- Sequenced the work as a phased migration — foundation, deal architecture, integration, then consolidation — to minimize disruption.
- Retrained the team on the unified data model so the new structure would actually be used.
The outcome
The Matchbox transformed PeopleFinders' revenue operations from a set of disconnected tools into a single, trustworthy source of truth. By rebuilding the deal architecture around real payments, straightening the billing-to-CRM integration, cleaning the underlying data, and consolidating two brands into one model, we gave leadership a clean line of sight from pipeline to revenue for the first time — proving that reliable growth reporting starts with the plumbing, not the dashboard.
Focus
Operational Efficiency & Scalability
FAQ
About this
engagement.
A rebuilt revenue operations system in HubSpot: a payment-triggered subscriptions pipeline where one deal equals one real payment, a direct Chargebee integration replacing an error-prone middle-layer sync, and a reporting model with real-time MRR by brand and segment.
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