Operations Escalation Lead

CloudTrucks is the virtual trucking carrier and leading technology and service provider for trucking entrepreneurs. Our mission is simple: to empower truck drivers—one of our nation's most essential workforces—with the tools they need to earn more, stress less, and grow their trucking businesses. We provide a complete business management platform for owner-operators and small trucking carriers, and our world-class software engineering, data science, and operations processes keep costs low for owner-operators.
As Operations Escalation Lead, you'll be the critical link between our owner-operators, broker partners, and internal teams when shipments face challenges. You'll leverage our platform and your logistics expertise to resolve complex issues quickly, maintain service quality, and ensure our drivers and broker partners stay confident in CloudTrucks' reliability. When drivers win, we win—and you'll play a key role in making that happen.

• Resolve high-priority escalations including delivery delays, load issues, driver breakdowns, and broker concerns

• Serve as the primary point of contact for critical incidents affecting owner-operators and brokers

• Coordinate across drivers, brokers, and internal teams (dispatch, customer success, engineering) to troubleshoot and resolve issues in real-time

• Investigate root causes of service failures and document solutions to prevent recurrence

• Monitor at-risk loads proactively and intervene before issues escalate

• Communicate clearly and empathetically with all stakeholders during high-pressure situations

• Partner with our product and engineering teams to surface platform improvements based on recurring operational challenges

• Track escalation metrics and identify trends to drive continuous improvement

• 2-4 years in trucking, freight brokerage, or logistics operations with direct carrier and broker interaction

• Proven experience managing urgent escalations and resolving complex operational problems

• Strong decision-making skills with comfort navigating ambiguous situations and making judgment calls with incomplete information

• Strong understanding of FTL operations, driver challenges, and broker requirements

• Exceptional communication skills and ability to remain composed under pressure

• Strong project management skills with ability to juggle multiple escalations simultaneously and prioritize effectively

• Tech-savvy with experience using TMS, dispatch software, or logistics platforms

• Flexible availability to support operations across time zones and occasional off-hours escalations

• Self-motivated problem-solver who thrives in fast-paced, ambiguous environments

• Experience working with owner-operators or small fleet operations

• Familiarity with digital freight platforms or freight tech startups

• Knowledge of trucking compliance, FMCSA regulations, and ELD systems

• Background in customer success or