Inspection Report Writing Software Transformation
Situation
I was leading product, finance, and operations at WIN, one of the largest and fastest-growing home inspection companies (300+ inspectors across 40+ states). Despite our rapid growth, issues with our inspection report writing software were limiting growth and creating business risks. Midway through addressing these issues, the software vendor announced immediate end-of-support and sunset of the software with only 10 months to complete our transition.
Task
The challenge was to:
- • Identify or build a replacement inspection report writing software platform
- • Build an engineering and product organization from scratch
- • Train and migrate 300+ inspectors within 10-month deadline
Action
- • I consolidated findings from 100+ user interviews and analyzed user feedback to identify critical pain points. I analyzed 20+ alternative vendor solutions and found that other options had similar pain points. It was clear that we would need to build our own software and team in-house.
- • I developed a product strategy and created initial prototypes to secure stakeholder buy-in. I oversaw MVP development and led weekly inspector meetings and feedback loops via Test Flight. I designed a scalable microservices architecture for platform performance and AI-powered workflows to reduce inspector writing time.
- • I built a product / engineering team of 12. I established sprint cadences and led code reviews.
- • I led the effort to get inspector buy in, achieve production readiness and execute the migration.
Result
WIN transformed a critical business threat into a major competitive advantage by establishing in-house technical capabilities, dramatically improving inspector productivity and satisfaction, and unlocking new revenue growth.
Key Metrics
- • 50% reduction in inspection time (6-7 hours → 3-3.5 hours)
- • 300+ inspectors migrated within 10 months
- • 22 month timeline start to full deployment
- • 0% data loss vs. 15-20% in legacy system
- • 99.9% system uptime zero critical failures during migration
- • $5M+ new revenue unlocked through 30+ inspection types
Inspector Feedback
"The app is awesome, I get the reports done basically the moment I complete the inspection, super great." — Don D., CA
"I just wanted to let you know that I completed a full inspection home report in under 90 minutes yesterday. That is an absolute first for me." — Tim R., VA
"The new report writer is a game changer—it saves me significant time, reducing the time spent on each report from 2 hours to 20 minutes." — John M., CA
"Full home, appliance recall, wind mitigation, four-point, pool inspection. Five hours, reports submitted on site." — Josh S., FL