Jen sits down with Bryan Ossa, Co-Founder and COO of Cartographer Consulting, and one of the four finalists selected for the AI & Tech Showdown opening keynote at TMSA ELEVATE.Bryan shares the story behind a CRM transformation for a transportation brokerage managing more than 1,000 shipments per month. Faced with notification overload, duplicate records, and conflicting automation, the company was struggling to keep track of customer requests and was close to abandoning its CRM altogether.In this episode, Jen and Bryan explore the operational realities behind CRM success, why over-engineering automation can create more problems than it solves, and what it takes to turn a system teams avoid into one they actually rely on.Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.