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Mayday
An AI-powered calendar assistant that helps you organize your schedule for maximum productivity.
What it does
Unifies personal and professional calendars into a single, intelligent view. Features an AI 'Scheduling Assistant' that suggests the best times for meetings based on your preferences. Automatically protects 'Deep Work' slots to prevent burnout and meeting bloat. Includes a unified 'To-Do' list that syncs directly with calendar time-blocks. Provides 'Availability Links' that intelligently hide or show slots based on your current workload.
Why it works
Personalization: Unlike standard calendars, Mayday learns your 'ideal day' and works to preserve it. Focus: Actively prioritizes your time rather than just displaying it. Interoperability: Works seamlessly with Google Calendar, Outlook, and Apple Calendar. Automation: Removes the friction of the 'meeting dance' by automating availability management.
Category: Productivity
Team Size: 11-25
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As of 2026
Productivity
Revenue: $1M-$5M ARR
An AI-powered calendar assistant that helps you organize your schedule for maximum productivity.
Overview
Mayday is an intelligent calendar and scheduling platform designed to act as a personal chief of staff. It uses AI to analyze your work patterns, identify priorities, and automatically find the best times for meetings and deep work. By unifying multiple calendars and managing availability, it helps users reclaim their time and reduce the cognitive load of daily planning.
Funding status: Funded
Revenue source: Subscriptions
Customer type: B2C
Pricing: Freemium
Tech stack: React, Node.js, Swift, AWS
Platform: MacOS • iOS • Web
Integrations: Google Calendar, Microsoft Outlook, iCloud, Zoom, Slack
Founder story
Founded in 2019 by Jeremy J. and a team of software engineers in Toronto, Canada. The founders realized that while everyone had a calendar, no one was actually being 'managed' by it. They built Mayday to be the proactive assistant they needed to navigate their own complex startup schedules.
What it does
- Unifies personal and professional calendars into a single, intelligent view
- Features an AI 'Scheduling Assistant' that suggests the best times for meetings based on your preferences
- Automatically protects 'Deep Work' slots to prevent burnout and meeting bloat
- Includes a unified 'To-Do' list that syncs directly with calendar time-blocks
- Provides 'Availability Links' that intelligently hide or show slots based on your current workload.
Who it's for
- Founders and Executives
- Project Managers
- Knowledge Workers
- People with busy social/work balances
Why it works
- Personalization: Unlike standard calendars, Mayday learns your 'ideal day' and works to preserve it
- Focus: Actively prioritizes your time rather than just displaying it
- Interoperability: Works seamlessly with Google Calendar, Outlook, and Apple Calendar
- Automation: Removes the friction of the 'meeting dance' by automating availability management.
Growth strategies
- Targeted the 'Productivity Nerd' niche on platforms like Twitter and Product Hunt.
- Used a 'Build in Public' approach to gather feedback and build a community of early adopters.
- Leveraged a freemium model to drive high- volume signups before introducing Pro features.
- Raised $3M in Seed funding (2022) to accelerate their AI- driven 'Time Intelligence' engine.
Alternatives
Comparison overview
- Motion: More enterprise-focused task management; Mayday is the more 'assistant-like' personal schedule optimizer.
- Reclaim.ai: Better for automated habits; Mayday offers a more comprehensive cross-platform desktop and mobile app experience.
- Mayday is the top choice for individuals who want an AI-first approach to owning their day.