Hall Pass
AI-powered calendar automation for busy families
Hall Pass turns messy school, sport and family emails into structured calendar events — automatically. Built as an internal Pleasant Company product, it demonstrates our ability to turn a real-world pain point into a working AI-powered service that fits into existing family workflows.
The opportunity
Families receive a constant stream of emails from schools, sports clubs, appointments and extracurricular activities. Important details are often buried in long messages, PDFs, images, newsletters or links.
Hall Pass reduces that mental load by turning noisy communication into calendar-ready information.
The system
Progressive web application (mobile-first)
Cloud-based backend and processing pipeline
Email ingestion and parsing system
AI extraction using large language models (e.g. Gemini)
Calendar integration layer (Google, Outlook, Apple)
Event normalisation and scheduling engine
Highlights
Processes structured and unstructured inputs: emails, PDFs, images, newsletters and links
Works with existing email and calendar tools — no new workflow required
Uses natural language to decide what matters
Creates calendar events with dates, times, locations and notes
Supports summaries and digests for upcoming events
Tens of thousands of emails parsed since launch
From messy workflow to useful product
Hall Pass shows how we approach product incubation: find a real pain point, build around existing behaviour, and use technology where it removes friction.