Howie is an AI‑powered calendar management service backed by a 24/7 team of executive assistants that automates scheduling, rescheduling, conflict detection, and follow‑ups for busy professionals. It learns individual preferences, handles both work and personal events in real time, and operates on a SOC 2 Type II and ADA‑compliant platform to keep executives’ calendars optimized and secure.
Funding
$6M raised to dateRaised to date based on public sources. This may differ from the amount the company actually raised and is based only on what is publicly available on the internet.



3OFounders
Product
Problem
Professionals with dense meeting calendars spend excessive time coordinating, rescheduling, and managing conflicts, which reduces the time available for core work and strategic activities.
Solution
Howie combines state‑of‑the‑art AI with a 24/7 team of experienced executive assistants to automate calendar management end‑to‑end. The service handles meeting scheduling, conflict detection, calendar audits, and real‑time preference adjustments, allowing users to add, move, or cancel appointments via simple commands or email. Howie continuously learns individual scheduling rules and personal habits, proactively flags issues, and sends reminders or notifications when users run late. All interactions are secured with SOC 2 Type II and ADA compliance, ensuring data privacy while delivering a seamless, human‑like assistant experience.
Target Audience
Howie is designed for busy executives, founders, investors, and high‑growth teams who need to maximize productive time while maintaining a tightly coordinated calendar.
Features
- AI‑driven scheduling engine that books, reschedules, and cancels meetings across multiple participants and time zones
- Real‑time conflict detection and proactive alerts to prevent double‑booking
- Customizable rule engine that adapts to user‑defined preferences (e.g., meeting length, buffer times, recurring patterns)
- Integrated follow‑up handling, including sending calendar invites, confirming attendance, and managing Calendly links
- 24/7 support from world‑class executive assistants who intervene for complex or ambiguous requests
- Secure, compliant infrastructure (SOC 2 Type II, ADA) protecting calendar data and personal information
- Ability to manage non‑work events (e.g., personal appointments, sports schedules) alongside professional commitments