Courtney Tremaine

Courtney Tremaine is an accomplished Executive Sales Director and insurance industry leader with over 18 years of experience spanning health insurance, financial services, property and casualty, life, and commercial lines. A former high school basketball coach, she brings the same discipline, strategic mindset, and commitment to excellence from the court to building high-performing teams and service organizations. Throughout her career, Courtney has consistently driven compliance, retention, and scalable growth, earning recognition for her ability to develop leaders and optimize organizational performance. At the heart of Courtney’s work is a dedication to financial education as the foundation of financial freedom. She is deeply committed to teaching families how to manage money, build wealth, and make intentional decisions that create long-term stability. Through her co-ownership of Collective Legacy Investments, LLC, alongside Karissa Tremaine, Courtney equips families with the knowledge, tools, and strategies to achieve financial security and generational wealth, partnering with WealthWave and The How Money Works® Company to deliver impactful education and guidance. Courtney’s leadership philosophy is rooted in service, integrity, and accountability. She has successfully led large-scale teams, optimized operational processes, and implemented training programs that elevate performance across hundreds of agents, many frontline leaders and mid-level leadership. Whether guiding corporate teams or empowering families, her mission remains steadfast: to build systems, leaders, and legacies that endure, creating lasting impact for both individuals and communities.

• Life and Health

• California State University San Marcos - BBA

• 2021 Top Sales Director-Effectuated Sales

• LendaHand