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Highlights

 

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.

 

Actionable
Takeaways

Build Trust to Overcome Enterprise Resistance

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.

Meet Your Users Where They Are

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.

Iterate Fast by Embracing Founder-Led Sales

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.

Leverage AI with a First-Principles Approach

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.

ROI-Driven Sales Are Key in Tight Markets

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.

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