Customer Obsession & Agentic AI Power Ravenna’s Reinvention of Internal Ops

Most startups bolt AI onto old products.  ⁨@ravennahq⁩  reimagined the entire workflow. 

When we first met Kevin Coleman and Taylor Halliday, it was clear they weren’t just chasing the hype cycle. They were pairing AI-native architecture with deep founder-market fit, and rebuilding how internal ops work — from first principles.

Their new company, Ravenna, is going after a $160B+ market dominated by legacy players. But instead of being intimidated by incumbents, they got focused, making some smart moves that more early-stage teams should consider:

1) Speak with 30+ customers before writing a line of code 2) Define a clear ICP and pain points 3) Build natively for Slack — where support actually happens 4) Prioritize automation, iteration, and real workflow transformation 5) Stayed radically transparent with investors and early customers

At Madrona, we love backing teams that combine ambition with discipline — and Kevin and Taylor are doing just that. In this episode of Founded & Funded, they sit down with Madrona Managing Director Tim Porter and talk through their journey, what they’d do differently the second time around, and how they’re building a durable, agentic platform for internal support.

If you're a founder building in AI, SaaS, or ops — this conversation is full of lessons worth hearing.

Transcript: https://bit.ly/4ju2Cml

Chapters:  (00:00) Introduction (00:23) Meet the Founders: Taylor Halliday and Kevin Coleman (02:05) The Birth of Ravenna: Identifying the Problem (03:05) The Concept of Enterprise Service Management (04:02) The Journey from Idea to Execution (04:31) Customer Insights and Market Fit (06:42) Building a Next-Generation Platform (10:43) Slack Integration and AI Automation (14:37) Partnering with Slack: A Strategic Move (17:13) Leveraging Slack for Knowledge Management (20:13) Balancing Focus and Vision (21:07) Discovering ITSM: A Hidden Market (21:40) Expanding Beyond IT: The Universal Help Desk (24:30) ServiceNow and the AI Revolution (27:03) Building a Transparent and Collaborative Culture (29:37) Recruiting Top AI Talent (31:59) Navigating Market Realities and Customer Focus (37:59) Advice for Aspiring Founders