Playing the Long Game: Building a Lasting Freight Sales Career

Freight is a competitive industry and a long game at the same time. The people who build lasting careers in it understand both of those things — they compete hard every day while also investing in the relationships, the knowledge, and the leadership skills that compound over years. In this episode of The Journey Podcast, Will Jenkins sits down with Kevin McMaster, SVP of Sales and Operations at Flock Freight, to talk about what that looks like across a freight career spanning Coyote Logistics, multiple leadership transitions, and now a senior operating role at one of logistics technology's most interesting companies.

Kevin shares his immigration story and what building a career in the United States taught him about work ethic, adaptability, and the specific hunger that shapes the best freight sales performers. He talks about his early years at Coyote — the competitive environment, the mentors who shaped him, the grind that built his foundation — and what it took to develop from a strong individual contributor into a leader who could build and run teams.

The conversation covers the transition from selling to leading in freight: what changes in that shift, what stays the same, and what skills get you to a top performer level that don't get you to effective leadership without intentional development. Kevin also shares how he thinks about building freight sales organizations today — the talent they need, the culture that lets them perform, and the market context that shapes what winning looks like right now.

For freight professionals developing their leadership, explore Journey's executive search or build your career through The Freight Academy.