Howie

Verified

Email-based AI secretary that schedules and reschedules meetings by handling the back-and-forth.

4.3

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Pricing

Paid

About Howie

Howie is an AI scheduling secretary that works over email, SMS, and iMessage: users CC Howie on a thread and it negotiates times, sends invites, reschedules, and follows up until the meeting is booked. It learns individual scheduling preferences and manages calendars with a focus on doing one job - calendar management - rather than being a general assistant. The Seattle-based company raised a $6M seed round in 2025 and reports scheduling thousands of meetings per week for over a thousand paying customers.

Key Features

CC-based scheduling over email, SMS, and iMessage
Automatic follow-ups until meetings are booked
Rescheduling and conflict detection
Customizable scheduling preferences and rules
Calendar audits and focus-time protection
Team and Enterprise plans with custom billing and support

Pros & Cons

Pros

+ Handles the entire scheduling conversation end to end

+ Learns flexible, user-defined scheduling preferences

+ Works over email and messaging without a new app to learn

+ Deliberately narrow scope keeps it reliable at its one job

Cons

- Scheduling only - no broader email or task assistance

- Exact pricing is not published on the official site

- Historically centered on Google Calendar, limiting Outlook shops

Use Cases

Booking meetings by CC'ing Howie on an email threadCoordinating group meetings across busy schedulesRescheduling and clearing the calendar on short noticeFollowing up automatically when invitees go quietEnforcing personal scheduling preferences and focus time