Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Ryan Alshak, CEO & Founder of Laurel, a Gen AI timekeeping platform that has raised $55.7 Million in funding.

Here are the most interesting points from our conversation:

• Laurel's Core Offering: Laurel automates timekeeping for professional service firms like law, accounting, and consulting. By shifting from manual to AI-driven time tracking, Laurel helps users save time and ensures companies bill and collect for all work performed, boosting profits by 4-11%.
• The "Aha" Moment: Ryan's inspiration to create Laurel came from his own frustrations as a lawyer, where tracking time in six-minute increments felt dehumanizing and inefficient. He realized a machine should be reminding professionals of their work, not the other way around.
• Overcoming Enterprise Resistance: Ryan emphasized that competing with large incumbents in the enterprise space requires not just great technology but also building trust and social proof to overcome buyers' fear of adopting new solutions.
• Change Management & Flexibility: Initially, Laurel tried to force users into a new workflow. They pivoted to offer multiple ways to track time—manually, through automation, with timers, or via delegation—meeting users where they are to drive adoption.
• Importance of First Principles in AI: Ryan believes incumbents are struggling to adapt to AI because they’re retrofitting it into legacy systems. Building AI-first, Laurel delivers a superior user experience, which Ryan sees as critical to winning in the AI space.
• Founder-Led Sales to 8-Figure ARR: Laurel’s journey to $10 million ARR has been driven by a founder-led sales approach, with a small but focused team. Ryan emphasized the unique learning advantages this approach provides, enabling faster product iteration and market fit.