Leadership pipelines are under pressure. Companies are moving faster, roles are becoming more cross-functional, and high-potential talent is expected to deliver beyond narrow job descriptions earlier in their careers. At the same time, the World Economic Forum estimates that 39% of workers’ core skills will need to evolve by 2030 to keep pace with business change—raising the stakes for how organizations develop leaders from within. In that environment, career growth can’t just be vertical; it has to be adaptive. So what does it actually look like to build leadership readiness before the promotion, not after it? Welcome to Beyond the Ledger. In the latest episode, host Troy Ashby sits down with Brent Asavamonchai, Director of Analytics, Revenue Strategy and Pricing at Southwest Airlines, to unpack “spiral growth”—a development model where professionals keep excellence in their core role while intentionally expanding into adjacent responsibilities. The conversation spans Brent’s path across major travel and airline brands, lessons from M&A integrations, and how to coach emerging leaders through real-world stretch opportunities. What you’ll learn… What Is Spiral Growth?Spiral growth means staying excellent in your core role while deliberately taking on adjacent responsibilities that expand your skills and leadership range over time. Growing Without Changing TitlesBrent emphasizes that some of the most valuable career growth is often invisible on job titles because real development happens in stretch assignments, not just promotions. Building Relationships That Create OpportunityHe credits much of his impact to intentionally building cross-functional relationships early, so collaboration and influence are in place before major projects begin. Learning Leadership Through RotationRotating across functions like supply chain, sales, marketing, and revenue management gave him a broader business lens that made him a stronger, more empathetic leader. Leading Through M&A and ChangeBrent’s M&A experience taught him that successful transformation requires aligning technology, process, strategy, and people—not just integrating systems. Developing Leaders EarlyHis view is that leadership development starts long before a manager title by giving people ownership of cross-functional work and mentoring opportunities now. Why Feedback Fuels GrowthBrent sees direct, honest feedback as essential because even when it’s uncomfortable, it creates the self-awareness and course correction leaders need to improve. Building a Startup Inside a Big CompanyWhile launching Getaways by Southwest, he found that startup-style agility inside an enterprise works best when teams stay anchored to a clear long-term vision and short-term milestones. Leadership, Family, and Long-Term FulfillmentLooking back, he believes sustainable success comes from balancing work with a meaningful life outside it, because career achievement alone is not enough for long-term fulfillment. Brent Asavamonchai has built his career by leaning into growth — even when it’s uncomfortable. His path hasn’t been linear. Sometimes that meant stepping into entirely new roles and learning fast. Other times, it meant expanding roles he was already strong in by layering on new responsibilities and stretch opportunities. Both approaches pushed his career forward in meaningful ways. Brent has extensive experience leading through post-acquisition change, including integrating multiple vacation brands — CheapCaribbean, Southwest Airlines Vacations, and United Vacations — following the merger of Apple Leisure Group and Mark Travel. His work focused on evolving revenue strategy, aligning technology, and reshaping team skills to meet changing business needs. He also played a key role in rolling out the Getaways by Southwest product. A core part of Brent’s leadership philosophy is developing people. He believes in starting small, giving team members ownership of projects, creating mentorship opportunities, and using stretch and rotational assignments to build broader skill sets. He’s also candid about early career mistakes, especially around communication, and how those lessons shaped him as a leader. Brent has worked with three of the five largest U.S. airlines and brings a thoughtful, practical perspective on growth, leadership, and navigating change.
