[SaaS Series] Creating Happier Workplaces Through AI With Taylor Halliday

INspired INsider Podcast

Taylor Halliday is the Co-founder and CEO of Ravenna, an AI-powered helpdesk software company that simplifies IT support and internal operations for organizations. Under his leadership, Ravenna raised $15 million in funding from Madrona Venture Group and Khosla Ventures, gaining recognition for its innovative Slack-native platform that streamlines support for IT, HR, and revenue operations teams. Before founding Ravenna, Tylor served as Director of AI Engineering and New Products at Zapier and also completed a fellowship at Y Combinator, experiences that brought both technical depth and startup expertise to the company.

In this episode…

Internal operations often struggle to keep pace with modern technology. Companies are buried in employee requests, scattered knowledge bases, and clunky help desk systems. What if AI could bring clarity and automation to that chaos — transforming Slack and other team platforms into true hubs of support?

Taylor Halliday has helped shape the future of workplace operations by drawing on experience at Zapier, along with a fellowship at Y Combinator. He brings a blend of technical expertise and startup leadership to solving the challenges of modern internal support. Known for a customer-led approach to product development, Taylor focuses on intuitive design, automation, and data-driven decision-making that enable organizations to scale more effectively. His work highlights how the right mix of AI and human insight can transform team efficiency and build stronger, more resilient companies.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Taylor Halliday, Co-founder and CEO of Ravenna, to discuss how Ravenna is reinventing internal support, co-founder dynamics, the role of customer feedback, and key decisions behind growth and fundraising. Taylor also shares stories on winning early customers and why trust and speed are vital in client relationships.