Mid-Market's AI Playbook | Episode 04: Justin Bailie & Caleb Gawne

Most companies know they need AI, they just don't know where to start. In this episode, Caleb Gawne breaks down how mid-market companies can find the right AI opportunities, avoid scattered experimentation, and use automation to improve how work actually gets done. Caleb explains why AI only creates value when it is tied to a clear business goal. Many teams are experimenting with ChatGPT, Claude, Copilot, internal tools, workflow automation, and AI agents, but experimentation alone does not transform a business. Without a plan, AI can become another version of spreadsheet chaos: faster individual work happening outside the core systems, but not better coordination across the company. The real opportunity for mid-market companies is to start with operational bottlenecks, define the business outcome, and decide whether the right answer is AI, automation, better software, process improvement, or some combination of all four. Read the full article:   / mid-markets-ai-playbook-caleb-gawne-5sxcc   Subscribe to the newsletter:   / nobody-built-this-for-you-7458377253488361472   00:00 Meet Caleb and Kye 02:01 Start With Clear Goals 03:37 Quick Wins and Governance 09:45 Where Companies Get Stuck 15:20 AI vs Automation vs Process 20:27 Why Mid Market Moves Faster 27:38 Speed as Competitive Edge 29:48 Rapid Fire AI Questions Guest: Caleb Gawne, CEO and co-founder of Kye (www.kye.ai). Caleb has spent more than a decade building technology for industries where the work is complex, manual, and full of exceptions, including logistics, healthcare, insurance, and financial services. At Kye, he helps mid-market companies identify operational bottlenecks and deploy customized AI agents to improve how work gets done. #MidMarket #WorkflowAutomation #AIStrategy #ProcessAutomation #AIAdoption #BusinessAutomation