Howie, a Seattle-based startup offering an AI-powered scheduling assistant, has secured $6 million in a seed funding round. The company also announced its public launch, revealing it already serves more than 1,000 paying customers who use the tool to automate meeting coordination directly from their email inboxes.
Key Takeaways
- Howie raised $6 million in a seed round led by venture capital firm True Ventures.
- The company launched publicly with an existing base of over 1,000 paying customers.
- The AI assistant operates within email to coordinate schedules, manage calendars, and send follow-ups.
- Howie reports scheduling over 5,000 meetings per week and has seen 50% average monthly growth in 2025.
How the Email-Based AI Assistant Functions
Howie is designed to function as a virtual executive assistant for professionals who frequently schedule external meetings. Users interact with the system by including it on an email thread, similar to copying a human assistant.
Once included in an email chain, the AI takes over the task of coordinating a suitable meeting time for all participants. Its responsibilities include proposing times, confirming a final slot, sending calendar invitations, and following up if a response is delayed. The system can also audit a user's schedule to identify and flag potential conflicts before they occur.
The primary users of the service include startup founders, venture capitalists, journalists, consultants, and recruiters. According to the company, these professionals rely on the tool to manage high volumes of external communication and scheduling demands.
A Crowded but Evolving Market
The market for AI-powered productivity tools has expanded rapidly. Companies like Perplexity have recently introduced similar email assistants. The sector has also seen challenges, as demonstrated by the closure of Xembly, another Seattle-based AI assistant startup that had previously raised $15 million.
Details of the $6 Million Investment
The $6 million seed funding round was led by True Ventures, a prominent venture capital firm. The investment signals confidence in Howie's approach to automated scheduling and its early market traction.
A notable group of individual and institutional investors also participated in the round. This includes Jason Calacanis, Perplexity CEO Aravind Srinivas, Superhuman founder Rahul Vohra, and Jordi Hays of TBPN. Other backers include Sophia Amoruso of Trust Fund, Turner Novak of Banana Capital, and Lindel Eakman of Foundry Group.
"I could not live without Howie at this point," said investor Diego Oppenheimer, a Seattle-based tech veteran, highlighting the product's value to its early users.
This diverse investor base, which also includes Resolute Ventures, PJC, and Roo Capital, underscores broad interest in solving the persistent challenge of professional scheduling.
Customization and Accuracy as Key Differentiators
Howie aims to distinguish itself in the competitive AI assistant market through enhanced customization and a focus on accuracy. The company employs a hybrid model that combines artificial intelligence with human oversight to ensure reliability.
Personalized Scheduling Rules
Users can define their specific scheduling preferences in an open-ended document. This allows the AI to adapt to individual workflows. For example, a user can set rules such as, "if it’s a pitch call, set it to 25 minutes and use Zoom," or specify preferred days and times for certain types of meetings.
Early Growth Metrics
Since its private beta, Howie has been scheduling more than 5,000 meetings each week. The company reports that its monthly recurring revenue and usage have grown by an average of 50% month-over-month throughout 2025.
A Hybrid AI and Human Approach
To maintain a high level of accuracy, Howie processes scheduling tasks using multiple fine-tuned large language models. When the system encounters a request with a high degree of uncertainty, the case is automatically escalated to a human reviewer. This two-tiered process is designed to deliver a level of reliability comparable to a human executive assistant, minimizing errors and misunderstandings.
The company offers two pricing tiers for its service. The standard plan is priced at $25 per month, while a premium version is available for $95 per month. The premium plan includes additional features, such as the ability for users to rename their AI assistant.
Company Background and Future Outlook
Howie was co-founded by CEO Austin Petersmith and Dave Newman. The pair first collaborated at Assembly in 2013 and experimented with a prototype for an AI assistant in 2015. At the time, they concluded that the technology and market were not yet mature enough for the concept.
"Now it’s not too early, so here we are," Petersmith stated, indicating their belief that the timing is now right for AI-driven scheduling tools.
Petersmith has prior entrepreneurial experience, having founded Capiche, a company later acquired by Vendr. The Howie team, based in Seattle's Fremont neighborhood, consists of nine people, five of whom are former company founders. This includes two alumni of the prestigious Y Combinator startup accelerator.
With fresh capital and a growing customer base, Howie is positioned to scale its operations and further refine its technology as it competes for a share of the expanding AI productivity market.