Ready to launch your own podcast? Book a strategy call.
Frontlines.io | Where B2B Founders Talk GTM.
Strategic Communications Advisory For Visionary Founders
Conversation
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.
Recommended Founder
Interviews
Bob van Luijt
CEO and Co-Founder of Weaviate
Bob van Luijt, CEO and Co-Founder of Weaviate: Over $67 Million Raised to Power the Future of Vector Databases
Tom Trowbridge
Co-Founder of Fluence Labs
Tom Trowbridge, co-founder of Fluence Labs: $9 Million Raised to Build the Future of Decentralized P2P Computing
Jorge Penalva
CEO & Co-Founder of Lang AI
Jorge Penalva, CEO of Lang.ai: $40 Million+ Raised to Build the Customer Experience Operations Category
Deon Nicholas
CEO & Co-Founder of Forethought
Deon Nicholas, CEO & Co-Founder of Forethought: $92 Million Raised to Power the Future of Customer Support with AI
Daniele Grassi
CEO of Axyon AI
Daniele Grassi, CEO of Axyon AI: $5.5 Million Raised to Power the Future of Financial Markets with AI
Davit Baghdasaryan
Co-Founder and CEO of Krisp
Davit Baghdasaryan, Co-Founder and CEO of Krisp: $19 Million Raised to Build the Voice Productivity Category
Damien Garot
Stellar of Stellar
Damien Garot, CEO & Co-Founder of Stellar: $9.3M Raised to Build the Future of Reliable Internet Connectivity for Autonomous Vehicles
Ravin Thambapillai
CEO and Co-Founder of Credal
Ravin Thambapillai, CEO and Co-Founder of Credal: $5 Million Raised to Build the Future of AI Security
Inna Sela
CEO & Founder of illumex
Inna Tokarev Sela, CEO & Founder of illumex: $13 Million Raised to Power the Future of Enterprise LLM Deployments
Johannes Peeters
Co-Founder & CEO of VoxelSensors
Johannes Peeters, Co-Founder & CEO of VoxelSensors: $7 Million Raised to Build the Future of Spatial Computing
Alon Talmor
CEO & Founder of Ask-AI
Alon Talmor, CEO & Founder of Ask-AI: $20 Million Raised to Power the Future of Enterprise AI
Richard Potter
Co-Founder and CEO of Peak
Richard Potter, Co-Founder and CEO at Peak: $118 Million Raised to Power the Future of AI-Enabled Businesses
Linda Watkins
SVP of Marketing of Edge Impulse
The Founder Whisperer: A Marketing Leader’s Guide to Technical CEOs
Joe Witt
CEO & Co-Founder of Datavolo
Joe Witt, CEO & Co-Founder of Datavolo: $21 Million Raised to Unlock the Potential of Unstructured Data for AI
Darko Vukovic
CEO & Founder of PolyAPI
Darko Vukovic, CEO & Founder of PolyAPI: $5 Million Raised to Transform Enterprise Middleware Through Native Code Developm
Jonathan Corbin
CEO & Co-Founder of Maven AGI
Jonathan Corbin, CEO and Co-Founder of Maven AGI: $28 Million Raised to Build the Future of Customer Experience
Mike Conover
CEO & Co-Founder of Brightwave
Mike Conover, CEO & Co-Founder of Brightwave: $6M Raised to Build the Future of AI-Powered Investment Research
Ryan Sevey
CEO of Mantium
Ryan Sevey, CEO of Mantium: $12 Million Raised to Help Teams Deploy and Monitor their AI Process Automations
David DeWolf
CEO & President of Knownwell
David DeWolf, CEO & President of Knownwell: $2 Million Raised to Build the Future of Commercial Intelligence
Jorge Torres
CEO and Co-Founder of MindsDB
Jorge Torres, CEO and Co-Founder of MindsDB: $50 Million Raised to Enable Developers to Integrate Machine Learning into Applications
Rich Taylor
Vice President of Seek AI
Rich Taylor, VP of Marketing at Seek AI: $10.5 Million Raised to Transform Data Analysis with Generative AI
Krish Ramineni
CEO of Fireflies
Krish Ramineni, CEO of Fireflies: $19 Million Raised to Build the Future of AI Meeting Assistants
Harry Xu
CEO and Co-Founder of Breeze ML
Harry Xu, CEO and Co-Founder of Breeze ML: $4.6 Million Raised to Create the Future of AI Governance
Igor Jablokov
CEO of Pryon
Igor Jablokov, CEO of Pryon: $50+ Million Raised to Build the Future of Enterprise Knowledge Management
Alex Sambvani
CEO & Co-Founder of Slang AI
Alex Sambvani, CEO & Co-Founder of Slang AI: $20 Million Raised to Power the Future of Voice AI for Restaurants
Jason Corso
Co-Founder and Chief Science Officer of Voxel 51
Jason Corso, Co-Founder and Chief Science Officer of Voxel 51: $15.5 Million Raised to Build the Future of Developer Tools for Machine Learning
Patricia Thaine
Co-Founder & CEO of Private AI
Patricia Thaine, Co-Founder & CEO of Private AI: Over $11 Million Raised to Help Organizations Anonymize PII to Achieve Regulatory Compliance
Nikola Borisov
CEO & Co-Founder of Deep Infra
Nikola Borisov, CEO & Co-Founder of Deep Infra: $9 Million Raised to Build the Future of AI Model Hosting
Ashley Montanaro
CEO and Co-Founder of Phasecraft
Ashley Montanaro, CEO & Co-Founder of Phasecraft: $22 Million Raised to Build the Future of Quantum Software
Alan Cowen
CEO and Founder of Hume AI
Alan Cowen, CEO and Founder of Hume AI: Over $17 Million Raised to Measure and Improve How Technology Affects Human Emotion
Jonathan Dambrot
CEO and Founder of Cranium
Jonathan Dambrot, CEO and Founder at Cranium: $32 Million Raised to Power the Future of AI Security
Malte Pietsch
CTO & Co-Founder of Deepset
Malte Pietsch, CTO & Co-Founder of Deepset: $45 Million Raised to Build the Future of LLMs
Jonathan Schneider
CEO and Co-Founder of Moderne
Jonathan Schneider, CEO & Co-Founder of Moderne: $20 Million Raised to Build the Future of Code Remediation
Anand Gopalan
CEO and Co-Founder of Vayu Robotics
Anand Gopalan, CEO & Co-Founder of Vayu Robotics: $12.7 Million Raised to Build the Next Wave of Robotics Solutions
Anand Kulkarni
CEO of Crowdbotics
Anand Kulkarni, CEO of Crowdbotics: $58 Million Raised to Power the Future of Rapid Application Development
William Gaviria Rojas
Field CTO & Co-Founder of CoactiveAI
William Gaviria Rojas, Field CTO & Co-Founder of CoactiveAI: $44 Million Raised to Build the Future of Multimodal AI Applications
Jeong-Suh Choi
CEO of Bobidi
Jeong-Suh Choi, CEO Bobidi: Nearly $6 Million raised to Deliver Better, More Inclusive AI Solutions for Developers
Ofer Ronen
CEO & Co-Founder of Tomato.ai
Ofer Ronen, CEO & Co-Founder of Tomato.ai: $12 Million Raised to Build the Accent Softening Category
Roger Luo
Founder & Managing Partner of Embedding VC
Funding the Future: Roger Luo, Managing Partner at Embedding VC
Aron Kirschen
CEO of SEMRON
Aron Kirschen, CEO of SEMRON: $7.3M Raised to Build Ultra-Efficient 3D AI Chips
Matt Theurer
CEO & Co-Founder of HyperSpectral
Matt Theurer, CEO & Co-Founder of HyperSpectral: $8.5 Million Raised to Power the Future of AI-Powered Spectral Intelligence
Gabriel Bayomi Tinoco Kalejaiye
CEO and Co-Founder of Openlayer
Gabriel Bayomi, CEO and Co-Founder of Openlayer: $4.8 Million Raised to Power the Future of Machine Learning Testing
Christian Stein
CEO & Co-Founder of Threedy
Christian Stein, CEO & Co-Founder of Threedy: $11.5M Raised to Power the Future of Industrial 3D Computing Infrastructure
David Plon
CEO & Co-Founder of Portrait Analytics
David Plon, CEO & Co-Founder of Portrait Analytics: $10M Raised to Build an AI-Powered Thought Partner for Institutional Investors
Douwe Kiela
CEO and Co-Founder of Contextual AI
Douwe Kiela, CEO and Co-Founder of Contextual AI: $20 Million Raised to Build the Future of Enterprise Language Models
Meryem Arik
CEO & Co-Founder of Titan ML
Meryem Arik, CEO and Co-Founder of Titan ML: $2.8 Million Raised to Revolutionize LLM Deployment
Phillip Liu
CEO of Trustero
Phillip Liu, CEO of Trustero: $8 Million Raised to Build the Future of Compliance AI