Howie: The AI Assistant Revolutionizing How We Schedule Meetings

In the hustle of professional life, scheduling meetings can consume hours of valuable time each week. Imagine typing an email about needing to schedule a call, and simply adding “@Howie can arrange time for a 45min chat.” Within a few exchanges, the meeting is set, complete with Howie asking if you’d like to add any materials or agenda items to the meeting description. While this interaction feels remarkably human, Howie isn’t a person at all – it’s an artificial intelligence assistant that lives in your inbox and aims to become your trusted AI secretary.

This Seattle-based startup has quickly gained traction, recently securing $6 million in seed funding after attracting over 1,000 paying customers. The investment round was led by True Ventures, with participation from an impressive lineup of investors including Jason Calacanis, Perplexity CEO Aravind Srinivas, Rahul Vohra of Superhuman, and many others. The impressive investor roster signals strong confidence in Howie’s approach to solving a universal pain point for busy professionals. Functioning as a virtual executive assistant, Howie does much more than just coordinate calendars – it adds events, follows up when necessary, and even proactively audits schedules to identify potential conflicts before they become problems. Users simply need to cc Howie on an email thread, and the AI handles the rest, creating a seamless scheduling experience that feels like working with a highly competent human assistant.

The platform has found particular resonance among professionals who spend significant portions of their workweek on external calls. Startup founders navigating fundraising and sales, venture capitalists managing extensive deal flow, journalists coordinating interviews, and consultants or recruiters who live by their meeting schedules have all embraced Howie as a solution to scheduling headaches. The growth metrics tell the story of Howie’s value proposition – the company reports scheduling over 5,000 meetings weekly for its paying customers and has achieved an impressive 50% month-over-month growth in both recurring revenue and usage throughout 2025. These figures suggest that once professionals experience Howie’s capabilities, they quickly integrate it into their workflow as an indispensable tool.

While Howie enters a competitive market with numerous AI assistant startups vying to automate administrative tasks, its approach offers key differentiators that have helped it stand out. The company emphasizes customization and accuracy as its core strengths. Users define their preferences in an open-ended document, allowing for highly personalized instructions like “if it’s a pitch call, set it to 25 minutes and use Zoom.” This flexibility enables Howie to adapt to individual workflows rather than forcing users to conform to rigid system parameters. Behind the scenes, Howie employs a sophisticated technical approach, running tasks through multiple fine-tuned language models and escalating uncertain cases to human reviewers. This hybrid AI-human system delivers reliability comparable to a human executive assistant while maintaining the efficiency and availability advantages of artificial intelligence. The company offers tiered pricing with a standard plan at $25 monthly and a premium version at $95 monthly that includes additional features such as the ability to rename Howie to suit your organization’s branding.

The story of Howie’s founding reveals perfect timing in the AI evolution timeline. CEO Austin Petersmith and co-founder Dave Newman first collaborated at Assembly in 2013 and were ahead of their time when they prototyped an AI assistant in 2015. They ultimately shelved that early project, concluding the market wasn’t ready. Now, with advancements in language models and growing acceptance of AI in professional settings, they believe the moment is right. “Now it’s not too early, so here we are,” Petersmith explained to GeekWire. The timing aligns with broader AI adoption trends, as professionals increasingly seek tools that can handle routine tasks while allowing them to focus on higher-value work. Howie’s approach reflects a nuanced understanding of what professionals need – not just a scheduling tool, but an intelligent assistant that understands individual preferences and communicates naturally.

Operating from Seattle’s Fremont neighborhood, Howie has assembled an impressive nine-person team that includes five former founders, with two being Y Combinator alumni. This concentration of entrepreneurial experience likely contributes to the company’s rapid growth and product-market fit. Petersmith brings valuable experience from previously founding Capiche, which was successfully acquired by Vendr. The company has attracted additional investment from notable figures including Sophia Amoruso of Trust Fund, Turner Novak of Banana Capital, Gaby Goldberg of Rostra, Lindel Eakman of Foundry Group, as well as institutions like Resolute Ventures, PJC, and Roo Capital. Seattle tech veteran Diego Oppenheimer, another investor, offered perhaps the most telling endorsement: “I could not live without Howie at this point.” As AI continues transforming how we work, Howie represents a practical, immediately valuable application that solves a universal problem – making it a company to watch in the evolving landscape of AI productivity tools.