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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:
Breaking into large enterprises as a startup requires more than a great product. Ryan stressed that enterprises often avoid early-stage startups due to a lack of trust and social proof. Founders must focus on earning that trust through consistent delivery, strategic proof points, and customer success stories to combat the “nobody gets fired for buying IBM” mindset.
Ryan learned the hard way that forcing users into a new workflow can backfire. Instead, offer flexibility in how customers use your product. By allowing multiple ways to track time—AI-driven automation, manual entry, or delegation—Laurel increased adoption. This takeaway is especially useful for founders introducing transformative solutions in traditionally conservative industries.
Founder-led sales have been crucial to Laurel's growth to over $10 million in ARR. Ryan recommends that founders stay on the front lines of sales for as long as possible. Doing so helps capture valuable market feedback, accelerate learning, and improve product-market fit—particularly important when launching category-defining products.
Incorporating AI effectively isn’t just about adding AI to your product. Ryan believes incumbents are failing because they’re trying to fit AI into outdated workflows. Instead, build AI solutions from a first-principles perspective to optimize the user experience. This lesson highlights the importance of designing AI tools that truly enhance productivity rather than just automating existing inefficiencies.
When selling to enterprises, especially in challenging economic conditions, ROI must be clear and demonstrable. Laurel’s ability to show how it directly impacts clients' bottom lines—through time saved and money earned—became a critical competitive advantage. This reinforces the importance of quantifying and communicating the value your product provides to secure deals, particularly when budgets are tight.