ON THE MOVE: Transportation Sales & Marketing Success Stories

From 100 Workflows to 12: A CRM Reset with Bryan Ossa

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.

How B2B Buying Is Changing in Supply Chain and Logistics with Brian Ceraolo

Jen sits down with Brian Ceraolo, a long-time supporter of TMSA and a President & CEO at Peerless Media, to discuss insights from Peerless Media’s Annual B2B Marketing Trends Study. The research provides practical benchmarks for marketing teams across supply chain, logistics, material handling, robotics, and engineering to compare their strategies with industry peers.The conversation also explores findings from Peerless’ recent Buyer’s Journey study, which revealed a significant generational shift in how B2B buyers research, evaluate, and make purchasing decisions.Jen and Brian discuss what the data shows, what marketing teams may be getting wrong, and how companies in logistics and supply chain can better align their strategies with the expectations of today’s buyers.Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.

From Three Weeks to 45 Minutes: AI at JAXPORT with Jeff Price

Jen sits down with Jeff Price, Marketing Director at Jacksonville Port Authority (JAXPORT) and one of the four finalists selected for the AI & Tech Showdown opening keynote at TMSA ELEVATE.Jeff shares how his team is using AI to turn complex maritime trade data into actionable sales intelligence and how a newly developed “digital worker” is helping their marketing team accelerate research, reporting, and content creation without increasing headcount. With more than 20 years of maritime industry experience combined with hands-on AI development, Jeff offers a practical look at how emerging technology can help sales and marketing teams move faster and work smarter.In this conversation, Jen and Jeff discuss the real-world challenges that led to these tools, the measurable results already being seen at JAXPORT, and what attendees can expect when he takes the stage at the AI & Tech Showdown at TMSA ELEVATE.Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.

Designing the Future Workforce with Lindsey Trent

Jen sits down with Lindsey Trent, Co-Founder and President of Next Generation in Trucking, to talk about building the future workforce of the supply chain. Lindsey shares her own path into the industry, the mission behind Next Gen, and why creating clear entry points for students and early-career professionals is more important than ever.The conversation also highlights the growing partnership between TMSA and Next Generation in Trucking through the Future Forward Volunteer Program at TMSA ELEVATE, an initiative designed to bring supply chain students into the conference experience through hands-on involvement, networking, and exposure to the industry. With applications currently open, this episode gives listeners a behind-the-scenes look at why the program exists, who it’s for, and the impact it can have on both volunteers and companies investing in the next generation of talent.Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.

Community, Career, and Showing Up Where It Matters with Briana Irwin

Jen sits down with Briana Irwin, Marketing Manager at TCW, to talk about building a career in logistics while staying grounded in community. From her day-to-day role in transportation marketing to her involvement with TMSA’s CSR subcommittee, Briana shares how getting involved early has shaped her growth. She also reflects on her 11-year commitment to delivering Christmas gifts to children in remote villages in Guatemala, and how both her personal experiences and TCW’s culture of giving back influence the way she shows up professionally. It’s a conversation about growth, involvement, and finding purpose alongside your profession.Register for the 2026 TMSA ELEVATE Conference at events.tmsatoday.orgCheck out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.