ClickUp
Additional 20% off on any plan
Howie is an artificial intelligence platform that acts as a virtual executive assistant specializing in meeting planning, automating the coordination, rescheduling, and management of events directly from your email inbox. Simply by copying Howie into an email thread, it analyzes your preferences, suggests slots that work for participants, creates invitations, and tracks responses, eliminating time-consuming back-and-forth and scheduling conflicts so you can stay focused on your priorities.
Using a combination of advanced AI and human support in the background, Howie adjusts to your custom rules, manages multiple Google calendars, anticipates conflicts, and proactively tracks responses, all while integrating seamlessly into your existing workflows without requiring a complex application. This approach helps professionals, founders, and teams save time, reduce scheduling stress, and improve their daily productivity.
Howie is precise:
Just CC Howie and he’ll start scheduling, coordinating, or following up based on your message. He checks *all* of your calendars. He handles group scheduling with grace. He catches every detail buried downthread. He clicks booking links for you. He adds PTA meetings to your calendar. He picks up on your subtle instructions indicating priority.
Howie is proactive:
Howie always follows up and never drops the ball. He knows to check with you before scheduling an 8am on a school dropoff day. He reacts to your guidance, and commits it to memory. He is constantly scanning your calendar to make sure it's accurate, logistically possible, and reflective of your priorities.
Howie is programmable:
To customize Howie's behavior, just tell him what you want. Create rules around availability, buffers, durations, travel, etc. Give guidance on meeting types, locations, code phrases that indicate priority, event titles, conferencing, communication style etc. Howie will better understand your scheduling needs in a week than a typical EA would in a year.
Howie is human?
Howie's left brain consists of NVIDIA GPUs running powerful machine-learning algorithms and fine-tuned LLMs to ensure Howie never misses a beat. Howie's right brain is a team of bright former EAs who intervene as needed to ensure natural communication, human intuition, and adaptive problem solving. One of their core innovations is the technology that allows these two brains to work together.
Scheduling meetings is one of those tasks that never gets any easier. The back-and-forth, the time zone juggling, the follow-ups when someone goes quiet, the rescheduling when a conflict arises: for professionals who handle a high volume of external calls, it can eat up a surprising amount of time every single week. Howie tackles this problem not by giving you a better calendar tool, but by giving you an AI that acts like an executive assistant. You CC it in an email thread, it takes over, and it handles the rest.
The tool operates entirely within email. There’s no dashboard to learn, no app to install, and no booking link to share. Howie reads the email thread, understands the context, checks availability, coordinates with all participants, and sends the calendar invite. For the recipient of Howie’s emails, the experience is indistinguishable from receiving a message from a human assistant.
Howie offers two individual plans and a team plan. There is no free trial, though the pricing is significantly lower than the hourly cost of a human executive assistant. Plans renew monthly and can be canceled at any time.
| Plan | Price | Key features |
|---|---|---|
| Solo | $25/month | Email-based calendar assistant, AI scheduling, conflict detection, daily summary, Zoom and Google Meet integration |
| Pro | $95/month | Everything in Solo, plus the ability to rename Howie with a custom persona, and a white-label experience for client-facing use |
| Team | $95/month (per team) | Pro features for every team member, centralized billing, shared scheduling rules, and a premium experience across the organization |
1️⃣ If you are a freelancer or consultant:
For an independent professional who schedules a moderate number of client calls per month, the key question is whether a dedicated AI assistant is worth the subscription cost compared to a simpler self-service tool. Calendly remains the go-to choice for this type of user: it’s easy to set up, free for basic use, and familiar to the professionals on the other end of the scheduling request. Cal.com is a strong open-source alternative with a cleaner interface and greater flexibility at a lower cost. For freelancers who want something closer to Howie’s conversational approach without the premium price, Reclaim combines intelligent calendar blocking with automatic meeting scheduling and works across Google Calendar and Outlook. Lemcal, also available in the Freelance Stack , is worth considering for those who primarily schedule sales or discovery calls and want a branded booking experience.
2️⃣ If you are a startup:
In the early stages of a startup, founders typically juggle a high volume of investor calls, partner meetings, and hiring conversations all at once—and this is precisely where Howie’s value shines. For teams that need both scheduling and meeting insights in one place, Reclaim or Motion offer AI-powered calendar management that goes beyond simple booking to include time blocking and task prioritization. Savvycal is a thoughtful alternative to Calendly that lets the invitee overlay their availability on yours, which reduces the back-and-forth while providing a better experience than a basic booking link. For startups already deeply integrated into the Google Workspace ecosystem, Google Calendar’s native appointment scheduling combined with Gemini AI features may meet basic needs without requiring an additional subscription.
3️⃣ If you are a small or medium-sized business:
For organizations managing the schedules of multiple team members, the priority shifts toward centralized visibility and shared scheduling logic. Microsoft Bookings, included in most Microsoft 365 plans, handles multi-staff scheduling and external bookings reasonably well for businesses that already rely on Microsoft tools. Acuity Scheduling is a more powerful option for service-based businesses that need granular control over appointment types, buffers, and availability windows for multiple team members. For sales-heavy teams where scheduling is directly tied to pipeline management, HubSpot Meetings or Salesforce Scheduler integrate booking directly into the CRM workflow, eliminating the friction of switching between tools when a prospect books a call.
Otherwise, these other software programs may also be a good alternative to Howie.
