Leading Outdoor
I built and run the deal system behind Leading Outdoor's site acquisition. It carries every location from first screen to signed lease to filed permit.
- 1,350+
- locations tracked
- 25
- connected databases
- 19
- pipeline stages
- Multi-market
- acquisition footprint
- 15-year
- leases signed to permit
One deal record per site, built from an empty workspace and running end to end today.
A deal operating system.
Built from an empty workspace and run end to end — the CRM, outreach, lease, and permitting layer behind an LED billboard operator's site acquisition.
- Record depthEvery site is a ~40-field due-diligence record
- Pipeline modelA 19-stage lifecycle with a branch state for every way a deal dies
- Screening logicPass/fail bylaw screening kills 500+ weak sites in minutes
- AutomationFormulas, buttons, rollups, mail-merge, and AI search handle the busywork
Prospect
Qualified sites enter one record with ownership, constraints, outreach context, and next action attached.
Source of truthQualify
Traffic, visibility, zoning, and ownership get checked before a site moves to proposal.
Screening layerLease
Proposal, negotiation, redlines, and signatures track against the same record.
Commercial closePermit
Survey, engineering, design, and application work stays tied to the deal file until the permit package is ready.
Build readinessTwenty-five databases across five connected systems.
Five regimes, codified to pass/fail.
Separation distances, height caps, setbacks, and variance odds across five regimes, codified into reusable pass/fail criteria.
Sign-bylaw rules250+ stakeholders, one record.
177 property owners plus municipal officials and legal, survey, engineering, design, and traffic partners route through one deal record.
Owners · officials · partnersDaily list, weekly email.
Over 3.5 years: a Rolling Task List, a working-session dashboard, and an auto-compiling weekly summary that keeps leadership current.
RTL · dashboard · metrics email