WINspect Home Inspection Report Writer Software
A complete replacement of mission-critical inspection report writing software.
Company
WIN Home Inspection
Year
December 2022 - November 2023
Role
Product Manager & Technical Lead
The Challenge
WIN's inspectors relied on vendor software that was failing on multiple fronts: browser-based architecture caused 15-20% image loss due to cache failures, inspectors spent 6-7 hours per inspection (2-3 hours on-site, then 3-4 hours at home), new inspectors required 14 days of technical training due to confusing UI/UX, and the same software was used by competitors with no differentiation. In November 2023, the vendor announced immediate end-of-support with complete shutdown by September 30, 2024.
The Solution
I led the complete replacement of the system in 9 months, transforming from checklist-driven to input-driven inspection with photo-first and search-first workflows. Built a mobile-first, AI-enabled platform with offline reliability, reducing clicks from 15+ to 3 per defect and total inspection time by 50%.
Situation
I joined WIN as a leader in Product Development, inheriting a complex technical and business challenge. WIN was a leader in home inspection services with 200+ franchisees across 40+ states generating $30M+ in systemwide revenue, but our core technology was holding us back. Our inspectors relied on vendor software that was failing: browser-based architecture caused 15-20% image loss, inspectors spent 6-7 hours per inspection, new inspectors required 14 days of training, and there was no competitive differentiation. In November 2023, our vendor announced immediate end-of-support with complete shutdown by September 30, 2024, transforming a strategic initiative into an existential crisis.
Task
I was tasked with leading both the product strategy and technical architecture to: Replace the entire system in 9 months (typically requiring 18-24 months), transform inspector productivity with 40%+ time reduction target, enable business growth supporting 30+ inspection types (vs. 5 in legacy system), create competitive advantage through proprietary technology, and ensure zero disruption while migrating TBs of data and 100% of users seamlessly.
Actions
Discovery & Strategic Pivot (December 2022 - February 2023)
Conducted ethnographic research shadowing 10 inspectors, interviewed 50+ inspectors documenting pain points, analyzed 12 competing solutions, and developed the breakthrough thesis: shifting from checklist-driven to input-driven inspection with photo-first and search-first workflows.
Building the Foundation (February 2023 - December 2023)
Designed microservices architecture with search service using Elasticsearch, offline sync service with WatermelonDB, image processing pipeline, PDF generation service, and AI comment generation with GPT-3.5. Built team from 0 to 8 engineers and established technical standards.
Crisis Response & Acceleration (November 2023 - January 2024)
When vendor announced immediate sunset, showcased prototype at January 2024 convention despite incompleteness. Presented live demos to 200+ franchisees, facilitated feedback sessions collecting 200+ feature requests, and converted 20 skeptical power users into champions.
Sprint to Production (February - June 2024)
Executed dual-track approach: prioritized features using value/effort matrix, ran weekly user testing with 5-7 inspectors, led architecture reviews for 10x scalability, implemented AWS infrastructure, and personally debugged critical offline sync issues.
Migration & Launch (June - September 2024)
Architected migration of 10TB+ historical data, managed App Store submissions, deployed through Apple Business Manager, created interactive training reducing onboarding from 14 days to 2 days, and personally handled escalations during launch.
Process & Deliverables
Orders dashboard showing upcoming inspections with scheduling, client details, and offline download capabilities
Category-driven inspection interface with search-first workflow and integrated photo capture
Photo-first approach with integrated image management and organized gallery by inspection category
Technical architecture with offline sync, AI comment generation, and image processing pipeline
Live demo presentation to 200+ franchisees at January 2024 convention
Data migration dashboard showing successful transfer of 10TB+ historical data
Testimonials
"When inspectors at our convention gave a standing ovation to a software demo, I knew we had transformed not just our technology, but an entire profession's relationship with their tools."
Will Rosler
Product Manager & Technical Lead
"This technology convinced me not to retire. What used to take me until midnight now gets done before dinner."
Testimonial Placeholder
Senior Inspector
Results
The initiative delivered transformational outcomes: 50% reduction in total inspection time (6-7 hours → 3-3.5 hours), 100% user adoption in 3 months with all 200+ franchisees migrated by deadline, 85% reduction in training time (14 days → 2 days), 30+ inspection types supported unlocking $5M+ in new service revenue, 99.9% uptime with zero critical failures during migration, 0% data loss vs. 15-20% in legacy system, and supporting 400+ daily active users with 500K+ images/month.
Technical Stack
React Native, NodeJS, Python, AWS (ECS, Lambda, RDS, S3), Elasticsearch, WatermelonDB, GPT-3.5
Timeline
December 2022 - September 2024 (21 months)