The Challenge
Live event producers at comedy venues spend 15+ hours per week on manual administrative tasks instead of creative programming. They juggle multiple sales channels (Eventbrite, direct website, door sales) using error-prone spreadsheet coordination, leading to overbooking incidents, lost revenue, and operational chaos during show times.
- Manual inventory sync across 3-5 platforms with different formatting requirements
- 15+ hours weekly on administrative tasks vs. creative programming
- $5K-10K annual losses from overselling incidents
- Show-day check-in chaos with paper lists and confused staff
User Research Methodology
I conducted one-on-one validation sessions with five stakeholders at Cheaper Than Therapy Comedy: three co-producers, one bar manager, and the primary box office associate. Each session started with workflow mapping of current manual processes, followed by prototype demonstration and iterative feedback collection.
Development Process
Technical Architecture Decisions
I chose Supabase over alternatives like Neon because it provides real-time subscriptions, built-in authentication, row-level security policies, and edge functions—features I'd need to build from scratch with other solutions. This decision proved crucial for the multi-tenant architecture and real-time inventory sync requirements.
Development Workflow Evolution
I started with no-code platforms (Lovable, Bolt, v0) for rapid experimentation but found they eventually got stuck in self-created error loops. This led me to switch to Claude Code for the core platform development, using the no-code tools only for initial UI concepts and visual inspiration.
No-code platforms excel for rapid prototyping and stakeholder demos, but become limiting when building complex, interconnected features. Claude Code provided the flexibility needed for sophisticated API integrations and custom business logic.
Square API Integration Deep Dive
The most technically complex achievement was building automated scheduling logic that updates inventory item variant availability based on organization-specific configuration. The system handles single vs. double show nights, differentiating between door sales for early vs. late Friday/Saturday shows.
Automated Scheduling
Cron jobs update Square inventory variants at precise times based on venue's show schedule
Smart Monitoring
Email notifications classify runs (NO_OP, CRITICAL) with detailed execution metrics
Mobile-First UI
Box office management optimized for tablets with offline capability
Intelligent Search
Progressive attendee lookup across events with 7-day look-ahead/back
Technical Implementation
Email Monitoring System
I built a comprehensive monitoring system that tracks execution timing, classifies run types, and provides actionable feedback. The system monitors GitHub Actions delays, critical window execution, and business impact assessment.
- Execution timing: Expected vs. actual minute with delay calculations
- Business impact: CRITICAL, MODERATE, NONE classification
- Run classification: NO_OP, STANDARD, CRITICAL types
- Action details: Which variants changed and why
Box Office Management Features
The current UI handles complex real-world scenarios: full/partial check-ins, no-show marking, cross-event attendee search, comp ticket management with organizational policies, and offline-capable operations for unreliable venue WiFi.
API Integration Lessons
I discovered that Facebook and Google severely restrict API access for event publishing, making those integrations impractical. This taught me to validate API accessibility early in the planning phase. I'm now focusing on Eventbrite integration for bi-weekly event publishing as the next development priority.
Impact & Learning Outcomes
Technical Skills Developed
- Product Management: Feature prioritization under time constraints with real user feedback loops
- API Integration: Complex scheduling logic with error handling and monitoring
- User-Centered Design: Balancing powerful functionality with operational simplicity
- Stakeholder Management: Addressing AI concerns through disciplined architecture and gradual autonomy models
Cross-Industry Pattern Recognition
This project reinforced my ability to apply methodical problem-solving across domains. The inventory management concepts from live events could apply to restaurant reservations, equipment rentals, or any multi-channel booking scenario.
What's Next
Current development priorities include Eventbrite API integration for automated event publishing, enhanced box office UI based on initial user testing, and expanding the platform to support additional comedy venues in San Francisco.
- Eventbrite Integration: Bi-weekly event publishing with template system
- Multi-venue Support: Scale architecture for additional comedy venues
- Advanced Analytics: Show performance metrics and attendance patterns
- Customer Portal: Self-service transfer and refund capabilities
This project demonstrates my ability to combine technical implementation with user-centered design thinking, turning operational chaos into systematic efficiency through methodical problem-solving.