Howie.ai

AI calendar secretary that schedules by email, SMS and iMessage

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Screenshot of Howie.ai, AI calendar secretary that schedules by email, SMS and iMessage

What is Howie.ai?

Howie.ai is a proactive AI assistant tool. Howie is an AI calendar secretary that books meetings over email, SMS and iMessage, protects focus time, follows up with people who go quiet and keeps reminders, using a credit-based workspace plan.

Howie is an AI scheduling assistant that people loop into email threads, texts and iMessage conversations whenever a meeting needs to be arranged. Instead of sharing a booking page, the user copies Howie on a message, and he reads the thread, looks up the relevant calendars, proposes times in the right time zone and sends an invite once someone confirms. The same approach covers group threads, where he collects replies from several people and settles on a slot that works for everyone. Beyond booking, the product acts as a general calendar and admin aide. It can hold focus blocks, add buffers, commutes and travel time, watch for conflicts and overloaded days, and apply scheduling rules the user sets, such as a cap on back-to-back meetings. It also tracks follow-ups, sending nudges on a chosen cadence when someone goes quiet, keeps reminders and to-dos, and briefs the day. Teams can give the assistant a custom name, an email address on the company domain and a matching signature, so outside contacts see him as part of the team. The intended audience is busy founders, executives, sales and recruiting teams, and anyone whose calendar turns into a pile of back-and-forth messages. Howie works with Gmail and Google Calendar, Zoom, and tools such as Granola, Notion, Todoist and Linear, and the site mentions SOC 2 Type II compliance. Pricing is credit based, with a shared workspace pool and unlimited teammates. Among alternatives, Howie sits between scheduling-link tools, which still ask the other party to pick a slot, and human executive assistants. Its pitch is conversational handling inside the channels people already use, which makes it closer to a delegated secretary than a calendar app. Buyers who want only a self-service booking page, or who work outside the supported mail and calendar stack, may find a simpler tool fits better.

How do you use Howie.ai?

  1. 1Start a free account
    Use the start button on the homepage to create an account and connect Gmail and Google Calendar so Howie can read threads and check availability.
  2. 2Set your scheduling rules
    Tell Howie your preferences, such as focus blocks, buffers, travel time and limits on back-to-back meetings, so proposed times respect them.
  3. 3Loop Howie into a thread
    Copy Howie on an email or message a contact asks to meet. He reads the conversation, checks calendars and offers times.
  4. 4Set up follow-ups and reminders
    Ask Howie to nudge people who go quiet, for example twice at set intervals, and to track reminders and to-dos.
  5. 5Brand the assistant for your team
    On the team plan, choose a name, a company-domain email and a signature so Howie appears as part of your team.

Pros and cons

Pros

  • Handles scheduling inside email, SMS and iMessage threads, so other parties need no new appAI
  • Follows up automatically on a cadence the user sets when contacts stop replyingAI
  • Applies personal scheduling rules such as back-to-back limits, buffers and travel timeAI
  • Team plan allows unlimited teammates and a custom assistant name and company-domain emailAI
  • Connects to Gmail, Google Calendar, Zoom and task tools like Notion, Todoist and LinearAI

Cons

  • Credit-based pricing makes monthly cost hard to predict for heavy scheduling volumeAI
  • Homepage names only Google calendar and mail, so Outlook or Microsoft users may be left outAI
  • Acts on your behalf in messages to third parties, which requires trust and careful rule setupAI
  • Custom domain assistant email costs extra on top of the base planAI
  • No native mobile or desktop app is listed, interaction depends on email and messagingAI

How much does Howie.ai cost?

Free trial

The homepage offers a "Start for free" button, but does not describe the free tier's limits or duration.

Learn more

Pricing

Plans start at $25/mo with shared workspace credits ranging from 1,250 to 150,000 monthly. A custom assistant email adds $20/mo. Enterprise pricing is custom, with invoicing, DPA, SLA and dedicated onboarding.

Learn more

Support

Enterprise includes SLA, priority support and dedicated onboarding. Sales contact is by email at support@howie.com.

Integrations

Works with Gmail, Google Calendar, Zoom, iMessage, Granola, Notion, Todoist, Linear, PostHog and Stripe, plus many more.

Features

Email, SMS and iMessage scheduling, group thread coordination, booking links, automatic follow-ups, focus blocks, holds, buffers and travel time, conflict watching, reminders, to-dos, daily briefings, custom assistant name and email.

Frequently asked questions about Howie.ai

  • How much does Howie.ai cost?
    Plans start at $25/mo with shared workspace credits ranging from 1,250 to 150,000 monthly. A custom assistant email adds $20/mo. Enterprise pricing is custom, with invoicing, DPA, SLA and dedicated onboarding.
  • Does Howie.ai offer a free trial?
    The homepage offers a "Start for free" button, but does not describe the free tier's limits or duration.
  • How do you use Howie.ai?
    The walkthrough on this page covers 5 steps: 1. Start a free account 2. Set your scheduling rules 3. Loop Howie into a thread 4. Set up follow-ups and reminders 5. Brand the assistant for your team.
  • What platforms does Howie.ai support?
    Howie.ai is available on Web App.
  • What does Howie.ai integrate with?
    Works with Gmail, Google Calendar, Zoom, iMessage, Granola, Notion, Todoist, Linear, PostHog and Stripe, plus many more.
  • What are the limitations of Howie.ai?
    Credit-based pricing makes monthly cost hard to predict for heavy scheduling volume. Homepage names only Google calendar and mail, so Outlook or Microsoft users may be left out. Acts on your behalf in messages to third parties, which requires trust and careful rule setup.

Status

StatusActive
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Added11/12/2026

Platforms

Web App

Pricing

FreemiumSubscription